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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2904-o2905
https://doi.org/10.1107/S1600536810041346

1,8-Bis(4-amino­benzo­yl)-2,7-dimeth­­oxy­naphthalene

Takahiro Nishijima,a Kotaro Kataoka,a Atsushi Nagasawa,a Akiko Okamotoa and Noriyuki Yonezawaa*

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 2 October 2010; accepted 14 October 2010; online 23 October 2010)

The title compound {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C26H22O4N2, possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the mol­ecules inter­act through inter­molecular N—H⋯O hydrogen bonds between the amino and meth­oxy groups on the naphthalene ring systems and N—H⋯π inter­actions between the amino groups and the naphthalene rings. Furthermore, weak C—H⋯O hydrogen bonds and π–π stacking inter­actions between the benzene rings are observed. The centroid–centroid and inter­planar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent mol­ecules 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[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]). For related structures, see: Muto et al. (2010[Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.]); Nakaema et al. (2007[Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120.], 2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Watanabe et al. (2010a[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010a). Acta Cryst. E66, o329.],b[Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010b). Acta Cryst. E66, o403.]). For work-up procedure in the preparation of the title compound, see: Bellamy et al. (1984[Bellamy, F. D. & Ou, K. (1984). Tetrahedron Lett. 25, 839-842.]).

[Scheme 1]

Experimental

Crystal data

  • C26H22N2O4

  • Mr = 426.46

  • Monoclinic, C 2/c

  • 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[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.751, Tmax = 0.928

  • 17453 measured reflections

  • 1892 independent reflections

  • 1690 reflections with I > 2σ(I)

  • Rint = 0.056
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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

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) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+2]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y, z+{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041346/rz2496Isup2.hkl

checkCIF report


Comment top

In the course of our study on selective electrophilic aromatic aroylation of naphthalene core, peri-aroylnaphthalene compounds have proved to be formed regioselectively by the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). The aroyl groups at 1,8-positions of the naphthalene rings in these compounds are oriented in opposite direction. The aromatic rings in this molecule are clarified to be assembled with non-coplanar configuration resulting in partial disruption of π-conjugated ring systems. Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalenes such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), bis(4-bromophenyl) (2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al., 2010a), (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe et al., 2010b) and 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., in press). As a part of our continuous study on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, (I), a peri-aroylnaphthalene bearing amino groups, is discussed in this article.

An ORTEPIII (Burnett & Johnson, 1996) plot of title compound is displayed in Fig. 1. The molecule of (I) lies across a crystallographic 2-fold axis so that the asymmetric unit contains one-half of the molecule. Thus, the two benzoyl groups are situated in anti orientation. The benzoyl groups are twisted away from the naphthalene moiety, and the dihedral angle is 83.59 (5)°. The torsion angle between the carbonyl group and the naphthalene ring is -89.52 (13)° [O2—C7—-C8—-C13], and that between the carbonyl group and the benzene ring is 175.91 (10)° [C5—C4—C7—O2].

The molecular packing of (I) is mainly stabilized by intermolecular hydrogen bond and van der Waals interaction (Table 1).The amino groups interact with the methoxy groups [N1—H4···O1i = 2.26 (2) Å; symmetry code: (i)-x + 3/2, -y - 1/2, -z + 2] of the adjacent molecules along the b axis (Fig. 2). Moreover, molecules are linked by N—H···π interactions along the c axis (Fig. 3). Besides, relatively weak C—H···O hydrogen bonding, C14—H14B···O2ii[symmetry code: (ii) -x + 3/2, y - 1/2, -z + 3/2], and a π—π stacking interaction are observed. In the packing, the molecules form the column structure of stacked naphthalene rings by π—π interaction perpendicular to the bc plane with alignment by N—H···π interaction and C—H···O hydrogen bonding along the c axis of the unit cell (Fig. 4).

Related literature top

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

Experimental top

The title compound was prepared by reduction reaction of 1,8-bis(4-nitrobenzoyl)-2,7-dimethoxynaphthalene (486.4 mg, 1.0 mmol), which was obtained via electrophilic aromatic diaroylation reaction of 2,7-dimethoxynaphthalene with 4-nitrobenzoyl chloride, with stannous chloride dihydrate (2.256 g, 10 mmol) in EtOH (8.0 ml) at 343 K for 2 h. The reaction mixture was worked up by reference to the previously outlined procedure (Bellamy et al., 1984). Isolated yield 96%. Brown single crystals suitable for X-ray diffraction were obtained by recrystallization from methanol.

Spectral data: 1H NMR (300 MHz, CDCl3) δ 3.71 (6H, s), 4.02 (4H, s), 6.54 (4H, broad), 7.18 (2H, d, J = 8.7 Hz), 7.53 (4H, broad), 7.88 (2H, d, J = 9.6 Hz); 13C NMR (75 MHz, DMSO) δ 56.37, 111.59. 112.22, 122.11, 125.06. 127.41, 128.86, 131.15, 131.29, 153.09, 155.06, 192.49; IR (KBr): 3463.53 (N—H), 3374.82 (N—H), 1644.98 (C═O), 1595.81 (Ar), 1508.06 (Ar)cm-1; HRMS (m/z): [M + H]+ Calcd for C26H23O4N2, 427.1658; found, 427.1633; m.p.= 580.5–583.0 K(decomp).

Refinement top

All the H-atoms could be located in difference Fourier maps. The amine and aromatic hydrogen atoms were freely refined. The hydrogen atom of methyl groups were subsequently refined as riding atoms with C—H = 0.96 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

In the course of our study on selective electrophilic aromatic aroylation of naphthalene core, peri-aroylnaphthalene compounds have proved to be formed regioselectively by the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). The aroyl groups at 1,8-positions of the naphthalene rings in these compounds are oriented in opposite direction. The aromatic rings in this molecule are clarified to be assembled with non-coplanar configuration resulting in partial disruption of π-conjugated ring systems. Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalenes such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), bis(4-bromophenyl) (2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al., 2010a), (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe et al., 2010b) and 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., in press). As a part of our continuous study on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, (I), a peri-aroylnaphthalene bearing amino groups, is discussed in this article.

An ORTEPIII (Burnett & Johnson, 1996) plot of title compound is displayed in Fig. 1. The molecule of (I) lies across a crystallographic 2-fold axis so that the asymmetric unit contains one-half of the molecule. Thus, the two benzoyl groups are situated in anti orientation. The benzoyl groups are twisted away from the naphthalene moiety, and the dihedral angle is 83.59 (5)°. The torsion angle between the carbonyl group and the naphthalene ring is -89.52 (13)° [O2—C7—-C8—-C13], and that between the carbonyl group and the benzene ring is 175.91 (10)° [C5—C4—C7—O2].

The molecular packing of (I) is mainly stabilized by intermolecular hydrogen bond and van der Waals interaction (Table 1).The amino groups interact with the methoxy groups [N1—H4···O1i = 2.26 (2) Å; symmetry code: (i)-x + 3/2, -y - 1/2, -z + 2] of the adjacent molecules along the b axis (Fig. 2). Moreover, molecules are linked by N—H···π interactions along the c axis (Fig. 3). Besides, relatively weak C—H···O hydrogen bonding, C14—H14B···O2ii[symmetry code: (ii) -x + 3/2, y - 1/2, -z + 3/2], and a π—π stacking interaction are observed. In the packing, the molecules form the column structure of stacked naphthalene rings by π—π interaction perpendicular to the bc plane with alignment by N—H···π interaction and C—H···O hydrogen bonding along the c axis of the unit cell (Fig. 4).

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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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(Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of title compound with displacement ellipsoids drawn at the 50% probability level. The symbol_2 refers to symmetry code: -x + 1, y, -z + 3/2.
[Figure 2] Fig. 2. Side view of the N—H···O hydrogen bond (blue dashed lines) and the π—π interaction (red dashed lines).
[Figure 3] Fig. 3. Side view of the N—H···π interactions (dashed lines).
[Figure 4] Fig. 4. A partial packing diagram of the title compound, viewed down the b axis.
[8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone top
Crystal data top
C26H22N2O4F(000) = 896
Mr = 426.46Dx = 1.372 Mg m−3
Monoclinic, C2/cMelting point = 580.5–583.0 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54187 Å
a = 14.2996 (3) ÅCell parameters from 11162 reflections
b = 10.2811 (2) Åθ = 3.1–68.2°
c = 15.4306 (3) ŵ = 0.76 mm−1
β = 114.523 (1)°T = 193 K
V = 2063.90 (7) Å3Platelet, brown
Z = 40.40 × 0.30 × 0.10 mm
Data collection top
Rigaki R-AXIS RAPID
diffractometer		1892 independent reflections
Radiation source: rotating anode1690 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.00 pixels mm-1θmax = 68.2°, θmin = 5.5°
ω scansh = −17→17
Absorption correction: numerical
(NUMABS; Higashi, 1999)		k = −12→12
Tmin = 0.751, Tmax = 0.928l = −18→18
17453 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H 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 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C26H22N2O4V = 2063.90 (7) Å3
Mr = 426.46Z = 4
Monoclinic, C2/cCu Kα radiation
a = 14.2996 (3) ŵ = 0.76 mm−1
b = 10.2811 (2) ÅT = 193 K
c = 15.4306 (3) Å0.40 × 0.30 × 0.10 mm
β = 114.523 (1)°
Data collection top
Rigaki R-AXIS RAPID
diffractometer		1892 independent reflections
Absorption correction: numerical
(NUMABS; Higashi, 1999)		1690 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 0.928Rint = 0.056
17453 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.24 e Å−3
1892 reflectionsΔρmin = −0.37 e Å−3
178 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.77436 (7)−0.11857 (9)0.88398 (7)0.0426 (3)
O20.62425 (7)0.07379 (8)0.72735 (6)0.0341 (3)
N10.63099 (9)0.33681 (13)1.10437 (8)0.0405 (3)
C10.62489 (9)0.26028 (13)1.02908 (8)0.0307 (3)
C20.63071 (9)0.31736 (12)0.94876 (9)0.0311 (3)
C30.62524 (9)0.24184 (12)0.87347 (8)0.0293 (3)
C40.61301 (8)0.10665 (11)0.87440 (8)0.0268 (3)
C50.60412 (9)0.05115 (13)0.95329 (9)0.0311 (3)
C60.60986 (9)0.12582 (13)1.02970 (9)0.0333 (3)
C70.61101 (8)0.02784 (12)0.79446 (8)0.0266 (3)
C80.59675 (9)−0.11834 (12)0.79669 (8)0.0278 (3)
C90.5000−0.18296 (16)0.75000.0267 (4)
C100.5000−0.32223 (16)0.75000.0302 (4)
C110.59352 (11)−0.39011 (13)0.79714 (9)0.0355 (3)
C120.68471 (11)−0.32756 (13)0.84270 (9)0.0366 (3)
C130.68596 (9)−0.19016 (13)0.84184 (9)0.0328 (3)
C140.86976 (11)−0.18638 (16)0.93136 (11)0.0495 (4)
H14A0.9248−0.12460.95740.059*
H14B0.8815−0.24150.88660.059*
H14C0.8669−0.23850.98180.059*
H10.5936 (11)−0.0400 (16)0.9542 (10)0.038 (4)*
H20.6079 (12)0.0862 (14)1.0838 (11)0.039 (4)*
H30.6425 (15)0.2952 (19)1.1606 (14)0.068 (6)*
H40.6672 (15)0.413 (2)1.1123 (13)0.065 (5)*
H50.6425 (11)0.4089 (16)0.9514 (10)0.038 (4)*
H60.6305 (11)0.2772 (14)0.8178 (10)0.034 (3)*
H70.5900 (12)−0.4824 (17)0.7944 (11)0.047 (4)*
H80.7479 (13)−0.3756 (16)0.8739 (11)0.048 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0267 (5)0.0363 (6)0.0529 (6)0.0065 (4)0.0048 (4)0.0005 (4)
O20.0404 (5)0.0317 (5)0.0299 (5)−0.0019 (4)0.0141 (4)0.0015 (4)
N10.0409 (7)0.0464 (7)0.0354 (6)−0.0038 (6)0.0170 (5)−0.0089 (5)
C10.0217 (6)0.0375 (7)0.0311 (6)0.0004 (5)0.0091 (5)−0.0033 (5)
C20.0309 (6)0.0258 (7)0.0348 (7)−0.0006 (5)0.0117 (5)−0.0005 (5)
C30.0289 (6)0.0275 (7)0.0298 (6)0.0001 (5)0.0106 (5)0.0034 (5)
C40.0221 (6)0.0258 (6)0.0291 (6)0.0002 (4)0.0074 (4)0.0010 (4)
C50.0296 (6)0.0279 (7)0.0350 (7)−0.0015 (5)0.0126 (5)0.0032 (5)
C60.0321 (6)0.0383 (7)0.0308 (6)−0.0010 (5)0.0144 (5)0.0039 (5)
C70.0198 (5)0.0271 (6)0.0281 (6)0.0002 (4)0.0053 (4)0.0016 (4)
C80.0305 (6)0.0259 (7)0.0271 (6)0.0023 (5)0.0120 (5)0.0006 (4)
C90.0329 (9)0.0249 (9)0.0241 (8)0.0000.0136 (7)0.000
C100.0407 (10)0.0258 (9)0.0278 (8)0.0000.0180 (7)0.000
C110.0520 (8)0.0235 (7)0.0332 (7)0.0058 (5)0.0200 (6)0.0030 (5)
C120.0408 (8)0.0318 (7)0.0350 (7)0.0124 (6)0.0135 (6)0.0053 (5)
C130.0319 (7)0.0319 (7)0.0321 (6)0.0033 (5)0.0108 (5)0.0004 (5)
C140.0308 (7)0.0487 (9)0.0550 (9)0.0133 (6)0.0040 (6)−0.0041 (7)
Geometric parameters (Å, º) top
O1—C131.3712 (15)C6—H20.939 (15)
O1—C141.4331 (15)C7—C81.5189 (17)
O2—C71.2223 (14)C8—C131.3857 (17)
N1—C11.3756 (16)C8—C91.4308 (14)
N1—H30.92 (2)C9—C8i1.4308 (14)
N1—H40.92 (2)C9—C101.432 (2)
C1—C61.3996 (19)C10—C11i1.4132 (16)
C1—C21.4045 (17)C10—C111.4132 (16)
C2—C31.3724 (17)C11—C121.359 (2)
C2—H50.954 (16)C11—H70.950 (18)
C3—C41.4017 (17)C12—C131.4128 (19)
C3—H60.964 (14)C12—H80.965 (17)
C4—C51.3972 (16)C14—H14A0.9600
C4—C71.4662 (16)C14—H14B0.9600
C5—C61.3806 (18)C14—H14C0.9600
C5—H10.950 (16)
C13—O1—C14118.41 (11)C13—C8—C9120.11 (12)
C1—N1—H3117.1 (12)C13—C8—C7115.75 (10)
C1—N1—H4115.9 (12)C9—C8—C7123.98 (11)
H3—N1—H4113.7 (17)C8—C9—C8i124.66 (15)
N1—C1—C6121.01 (12)C8—C9—C10117.67 (8)
N1—C1—C2120.00 (12)C8i—C9—C10117.67 (8)
C6—C1—C2118.97 (11)C11i—C10—C11120.81 (17)
C3—C2—C1120.48 (12)C11i—C10—C9119.59 (8)
C3—C2—H5122.7 (8)C11—C10—C9119.59 (8)
C1—C2—H5116.7 (8)C12—C11—C10122.17 (13)
C2—C3—C4121.05 (11)C12—C11—H7121.2 (9)
C2—C3—H6122.9 (9)C10—C11—H7116.6 (10)
C4—C3—H6116.1 (9)C11—C12—C13118.78 (12)
C5—C4—C3118.09 (11)C11—C12—H8121.0 (10)
C5—C4—C7122.03 (11)C13—C12—H8120.2 (10)
C3—C4—C7119.88 (11)O1—C13—C8115.30 (11)
C6—C5—C4121.49 (12)O1—C13—C12123.02 (11)
C6—C5—H1119.3 (9)C8—C13—C12121.67 (12)
C4—C5—H1119.2 (9)O1—C14—H14A109.5
C5—C6—C1119.88 (11)O1—C14—H14B109.5
C5—C6—H2120.3 (9)H14A—C14—H14B109.5
C1—C6—H2119.7 (9)O1—C14—H14C109.5
O2—C7—C4122.92 (11)H14A—C14—H14C109.5
O2—C7—C8118.10 (10)H14B—C14—H14C109.5
C4—C7—C8118.92 (10)
N1—C1—C2—C3179.66 (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—C40.48 (18)C7—C8—C9—C10173.63 (8)
C2—C3—C4—C51.46 (17)C8—C9—C10—C11i−178.56 (8)
C2—C3—C4—C7−177.87 (10)C8i—C9—C10—C11i1.44 (8)
C3—C4—C5—C6−1.70 (17)C8—C9—C10—C111.44 (8)
C7—C4—C5—C6177.61 (10)C8i—C9—C10—C11−178.56 (8)
C4—C5—C6—C10.00 (18)C11i—C10—C11—C12179.69 (13)
N1—C1—C6—C5−179.93 (11)C9—C10—C11—C12−0.31 (13)
C2—C1—C6—C51.96 (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—O23.40 (17)C14—O1—C13—C12−0.25 (18)
C5—C4—C7—C81.21 (16)C9—C8—C13—O1179.77 (9)
C3—C4—C7—C8−179.48 (10)C7—C8—C13—O14.22 (15)
O2—C7—C8—C1389.52 (13)C9—C8—C13—C120.53 (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—C996.90 (12)C11—C12—C13—C80.64 (19)
C13—C8—C9—C8i178.46 (11)
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N1—H4···O1ii0.93 (2)2.26 (2)3.1708 (17)169.1 (18)
C14—H14B···O2iii0.962.573.5013 (18)165
N1—H3···Cgiv0.92 (2)2.50 (2)3.3301 (13)149.8 (18)
Symmetry codes: (ii) −x+3/2, −y+1/2, −z+2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H22N2O4
Mr426.46
Crystal system, space groupMonoclinic, C2/c
Temperature (K)193
a, b, c (Å)14.2996 (3), 10.2811 (2), 15.4306 (3)
β (°) 114.523 (1)
V (Å3)2063.90 (7)
Z4
Radiation typeCu Kα
µ (mm−1)0.76
Crystal size (mm)0.40 × 0.30 × 0.10
Data collection
DiffractometerRigaki R-AXIS RAPID
Absorption correctionNumerical
(NUMABS; Higashi, 1999)
Tmin, Tmax0.751, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections		17453, 1892, 1690
Rint0.056
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.114, 1.12
No. of reflections1892
No. of parameters178
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.37

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), SHELXL97(Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N1—H4···O1i0.93 (2)2.26 (2)3.1708 (17)169.1 (18)
C14—H14B···O2ii0.962.573.5013 (18)165
N1—H3···Cgiii0.92 (2)2.50 (2)3.3301 (13)149.8 (18)
Symmetry codes: (i) −x+3/2, −y+1/2, −z+2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x, −y, z+1/2.
 

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Sasagawa Scientific Research Grant from the Japan Science Society.

References

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2904-o2905
https://doi.org/10.1107/S1600536810041346
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