1-[(4-Chloro­phen­yl)(phenyl­imino)­meth­yl]-7-meth­oxy-2-naphthol–1,4-diaza­bicyclo­[2.2.2]octane (2/1)

Nagasawa, A.; Mitsui, R.; Kato, Y.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810034690

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2498

doi:10.1107/S1600536810034690

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1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)

Atsushi Nagasawa,^a Ryosuke Mitsui,^a Yuichi Kato,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

^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 24 August 2010; accepted 28 August 2010; online 4 September 2010)

In the crystal structure of the title cocrystal, 2C₂₄H₁₈ClNO₂·C₆H₁₂N₂, the 1,4-diazabicyclo[2.2.2]octane molecule is located on a twofold rotation axis and linked to the two triarylimine molecules by O—H⋯N hydrogen bonds, forming a 2:1 aggregate. C—H⋯Cl interactions are also observed. In the triarylimine molecule, the naphthalene ring system makes dihedral angles of 80.39 (6) and 82.35 (6)°, respectively, with the phenyl and benzene rings. The dihedral angle between these two latter rings is 87.09 (7)°.

Related literature

For our study of the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene and peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009 ). For related structures, see: Hijikata et al. (2010 ); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ); Watanabe, Nakaema, Muto et al. (2010 ); Watanabe, Nakaema, Nishijima et al. (2010 ).

Experimental

Crystal data

C₂₄H₁₈ClNO₂·0.5C₆H₁₂N₂
M_r = 443.93
Monoclinic, C 2/c
a = 25.0027 (5) Å
b = 9.92298 (18) Å
c = 20.0052 (4) Å
β = 114.621 (1)°
V = 4512.07 (16) Å³
Z = 8
Cu Kα radiation
μ = 1.71 mm⁻¹
T = 193 K
0.60 × 0.50 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.381, T_max = 0.548
39753 measured reflections
4125 independent reflections
3831 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.04
4125 reflections
295 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.89 (2)	1.86 (2)	2.7401 (18)	167.2 (18)
C20—H20⋯Cl1ⁱⁱ	0.95	2.78	3.6071 (17)	146
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034690/is2593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034690/is2593Isup2.hkl

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). Recently, we reported the crystal structures of several 1,8-diaroylated naphthalene homologues exemplified by bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe, Nakaema, Muto et al., 2010).

The aroyl groups in these compounds are bonded almost perpendicularly to the naphthalene rings at the 1,8-positions but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Moreover, the X-ray crystal structural analyses of 1-(4-substituted benzoylated)naphthalenes, i.e., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Okamoto & Yonezawa, 2008), 1-(4-nitrobenzoyl)-2,7-dimethoxynaphthalene (Watanabe, Nakaema, Nishijima et al., 2010) and methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al., 2010), have also revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. Contrarily, the benzene ring of (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008) is bonded to the naphthalene ring with nearly coplanar configuration in the opposite direction against the 2-hydroxy group. This crystal structure is stabilized by intramolecular hydrogen bond between 2-hydroxy group and the carbonyl group.

As a part of our continuous study on the molecular structures of this kind of homologous molecules, we have investigated imination of aroylated naphthalene derivatives. Triarylimine has been clarified to be synthesized effectively by imination with the aid of TiCl₄ and 1,4-diazabicyclo[2.2.2]octane (DABCO). The cocrystal of triarylimines and DABCO (2/1) was prepared directly from the reaction mixture.

An ORTEPIII (Burnett & Johnson, 1996) plot of the title cocrystal is shown in Fig. 1. In the crystal packing, one DABCO molecule is connected to two triarylimine molecules with two O—H···N hydrogen bonds (Fig. 2). The 2:1 comolecular unit of triarylimines and DABCO have twofold rotation symmetry, with the central DABCO molecule lying on the rotation axis. In triarylimine of the comolecular unit, the interplanar angles of phenyl ring (C18–C23) attached to nitrogen atom (N1) and benzene ring (C12–C17) attached to carbon atom (C11) against the naphthalene ring (C1–C10) are 80.39 (6) and 82.35 (6)°, respectively. Furthermore, the interplanar angle between the phenyl and benzene rings is 87.09 (7)°.

The molecular packing is mainly stabilized by intermolecular hydrogen bonds and van der Waals interactions. Triarylimine and DABCO are linked with intermolecular O—H···N hydrogen bond [O1—H1···N2 = 1.86 (2) Å]. The 2:1 comolecular units are aligned along the a axis (Fig. 3). The C—H···π interaction between the methylene hydrogen atom of DABCO molecule and the naphthalene ring is observed along the c axis [C5···H25A = 2.69 Å]. Furthermore, the hydrogen bond between the chlorine atom and the hydrogen atom of the phenyl ring (C18–C23) is observed along the b axis [Cl1···H20 = 2.78 Å].

Related literature top

For related structures, see: Hijikata et al. (2010); Mitsui, Nakaema, Noguchi & Yonezawa (2008); Mitsui, Nakaema, Noguchi, Okamoto, A. & Yonez (2008); Watanabe, Nakaema, Muto et al. (2010); Watanabe, Nakaema, Nishijima et al. (2010). For our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009).

Experimental top

To a solution of 1-(4-chlorobenzoyl)-2-hydroxy-7-methoxynaphthalene (0.2 mmol, 62.8 mg) in chlorobenzene (1 ml), a mixture of aniline (0.22 mmol, 20.5 mg), TiCl₄ (0.33 mmol, 62.4 mg), DABCO (1.32 mmol, 148.0 mg) and chlorobenzene (1 ml) was added by portions at 363 K under nitrogen atmosphere. After the reaction mixture was stirred at 398 K for 1.5 h, the resulting solution was filtrated to remove the precipitate. The solvent was removed under reduced pressure to give crude material. The crude material thus obtained was subjected to crystallization from CHCl₃/n-hexane to give the cocrystal of triarylimines and DABCO (2/1) as colorless block (m.p. 445.6–446.0 K, yield 19.5 mg, 22%).

Spectroscopic Data: ¹H NMR (300 MHz, DMSO-d₆) δ; 10.13, (s, 1H), 7.66–7.60 (m, 4H), 7.44 (d, 2H), 7.00 (t, 2H), 6.95 (d, 1H), 6.86–6.76 (m, 4H), 6.52 (d, 1H), 3.64 (s, 3H), 3.29 (s, 6H); ¹³C NMR (75 MHz, DMSO-d₆) 164.4, 158.2, 153.7, 151.0, 137.6, 135.7, 132.2, 130.3, 130.0, 129.7, 128.7, 128.2, 123.8, 122.9, 119.2, 115.1, 115.0, 114.9, 102.6, 55.1, 47.3; IR (KBr): 3407, 2937, 2592, 1625, 1585, 1509, 1227; HRMS (m/z): [M + H]⁺ calcd for C₂₄H₁₉ClNO₂, 388.1110; found, 388.1104.

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

	Fig. 1. The asymmetric unit of the cocrystal of triarylimine and DABCO, showing 50% probability displacement ellipsoids [symmetry code: (i) 1 - x, y, 3/2 - z].
	Fig. 2. The 2:1 comolecular unit of triarylimines and DABCO [symmetry codes: (i) 1 - x, y, -z; (ii) 1 - x, -y, 1 - z; (iii) x, -y, -1/2 + z]. The intermolecular O—H···N hydrogen bond are shown as dashed lines.
	Fig. 3. A partial crystal packing diagram of the cocrystal of triarylimine and DABCO, viewed down the b axis. The intermolecular O—H···N hydrogen bond are shown as dashed lines.

1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol– 1,4-diazabicyclo[2.2.2]octane (2/1) top

Crystal data top

C₂₄H₁₈ClNO₂·0.5C₆H₁₂N₂	F(000) = 1864
M_r = 443.93	D_x = 1.307 Mg m⁻³
Monoclinic, C2/c	Melting point = 445.6–446.0 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54187 Å
a = 25.0027 (5) Å	Cell parameters from 33487 reflections
b = 9.92298 (18) Å	θ = 3.6–68.2°
c = 20.0052 (4) Å	µ = 1.71 mm⁻¹
β = 114.621 (1)°	T = 193 K
V = 4512.07 (16) Å³	Block, colorless
Z = 8	0.60 × 0.50 × 0.40 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4125 independent reflections
Radiation source: rotating anode	3831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 3.9°
ω scans	h = −30→30
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −11→11
T_min = 0.381, T_max = 0.548	l = −24→24
39753 measured reflections

Refinement top

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0539P)² + 2.6288P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4125 reflections	Δρ_max = 0.44 e Å⁻³
295 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00076 (6)

Crystal data top

C₂₄H₁₈ClNO₂·0.5C₆H₁₂N₂	V = 4512.07 (16) Å³
M_r = 443.93	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 25.0027 (5) Å	µ = 1.71 mm⁻¹
b = 9.92298 (18) Å	T = 193 K
c = 20.0052 (4) Å	0.60 × 0.50 × 0.40 mm
β = 114.621 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4125 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3831 reflections with I > 2σ(I)
T_min = 0.381, T_max = 0.548	R_int = 0.026
39753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.44 e Å⁻³
4125 reflections	Δρ_min = −0.32 e Å⁻³
295 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

	x	y	z	U_iso*/U_eq
Cl1	0.091242 (19)	−0.01553 (5)	0.13553 (2)	0.06399 (16)
O1	0.39706 (5)	0.09386 (10)	0.35831 (6)	0.0414 (3)
O2	0.27685 (5)	−0.16378 (10)	0.60663 (6)	0.0454 (3)
N1	0.30621 (5)	0.22752 (11)	0.43787 (6)	0.0334 (3)
N2	0.52801 (5)	−0.05890 (12)	0.70856 (6)	0.0364 (3)
C1	0.35467 (5)	0.01095 (12)	0.43518 (7)	0.0285 (3)
C2	0.39665 (6)	−0.00014 (13)	0.40731 (7)	0.0320 (3)
C3	0.43819 (6)	−0.10588 (14)	0.43064 (8)	0.0372 (3)
H3	0.4684	−0.1102	0.4136	0.045*
C4	0.43495 (6)	−0.20190 (14)	0.47761 (8)	0.0369 (3)
H4	0.4623	−0.2743	0.4916	0.044*
C5	0.39191 (6)	−0.19608 (13)	0.50592 (7)	0.0319 (3)
C6	0.38745 (6)	−0.29572 (14)	0.55401 (8)	0.0381 (3)
H6	0.4123	−0.3726	0.5650	0.046*
C7	0.34832 (7)	−0.28366 (14)	0.58474 (8)	0.0393 (3)
H7	0.3458	−0.3518	0.6167	0.047*
C8	0.31135 (6)	−0.16910 (14)	0.56896 (7)	0.0345 (3)
C9	0.31213 (6)	−0.07365 (13)	0.51986 (7)	0.0311 (3)
H9	0.2857	0.0004	0.5079	0.037*
C10	0.35246 (5)	−0.08518 (12)	0.48682 (7)	0.0283 (3)
C11	0.30795 (5)	0.11744 (13)	0.40603 (7)	0.0296 (3)
C12	0.25612 (5)	0.08458 (13)	0.33587 (7)	0.0306 (3)
C13	0.23887 (6)	−0.04876 (14)	0.31739 (7)	0.0347 (3)
H13	0.2624	−0.1194	0.3474	0.042*
C14	0.18793 (6)	−0.08022 (14)	0.25584 (8)	0.0370 (3)
H14	0.1758	−0.1712	0.2442	0.044*
C15	0.15531 (6)	0.02355 (15)	0.21194 (7)	0.0378 (3)
C16	0.17224 (6)	0.15721 (15)	0.22735 (8)	0.0396 (3)
H16	0.1498	0.2271	0.1955	0.048*
C17	0.22236 (6)	0.18705 (14)	0.28987 (7)	0.0350 (3)
H17	0.2339	0.2783	0.3016	0.042*
C18	0.35302 (6)	0.26745 (13)	0.50447 (7)	0.0321 (3)
C19	0.41007 (6)	0.28720 (13)	0.51060 (8)	0.0355 (3)
H19	0.4198	0.2637	0.4710	0.043*
C20	0.45241 (6)	0.34079 (14)	0.57415 (8)	0.0396 (3)
H20	0.4910	0.3558	0.5775	0.048*
C21	0.43962 (7)	0.37310 (15)	0.63327 (8)	0.0414 (3)
H21	0.4692	0.4094	0.6770	0.050*
C22	0.38341 (7)	0.35180 (15)	0.62785 (8)	0.0423 (3)
H22	0.3744	0.3725	0.6684	0.051*
C23	0.34011 (6)	0.30065 (14)	0.56397 (8)	0.0385 (3)
H23	0.3014	0.2880	0.5605	0.046*
C24	0.24275 (8)	−0.04438 (17)	0.59824 (10)	0.0523 (4)
H24A	0.2229	−0.0483	0.6313	0.063*
H24B	0.2133	−0.0374	0.5473	0.063*
H24C	0.2686	0.0345	0.6103	0.063*
C25	0.47037 (7)	0.00787 (16)	0.67146 (8)	0.0437 (3)
H25A	0.4462	−0.0418	0.6259	0.052*
H25B	0.4761	0.1008	0.6576	0.052*
C26	0.56208 (7)	0.01255 (17)	0.77789 (9)	0.0462 (4)
H26A	0.5679	0.1075	0.7673	0.055*
H26B	0.6013	−0.0299	0.8030	0.055*
C27	0.51789 (7)	−0.19821 (15)	0.72649 (9)	0.0432 (3)
H27A	0.5562	−0.2434	0.7538	0.052*
H27B	0.4962	−0.2491	0.6805	0.052*
H1	0.4247 (9)	0.075 (2)	0.3425 (11)	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0550 (3)	0.0596 (3)	0.0526 (3)	0.00847 (19)	−0.0022 (2)	−0.00729 (19)
O1	0.0492 (6)	0.0401 (5)	0.0517 (6)	0.0113 (4)	0.0378 (5)	0.0121 (4)
O2	0.0642 (7)	0.0358 (5)	0.0564 (6)	0.0060 (5)	0.0453 (6)	0.0087 (5)
N1	0.0348 (6)	0.0318 (6)	0.0381 (6)	0.0051 (4)	0.0197 (5)	0.0033 (5)
N2	0.0388 (6)	0.0394 (6)	0.0383 (6)	0.0020 (5)	0.0233 (5)	0.0011 (5)
C1	0.0299 (6)	0.0273 (6)	0.0310 (6)	0.0027 (5)	0.0154 (5)	0.0006 (5)
C2	0.0356 (7)	0.0306 (7)	0.0353 (7)	0.0021 (5)	0.0202 (6)	0.0017 (5)
C3	0.0366 (7)	0.0392 (8)	0.0454 (7)	0.0071 (6)	0.0265 (6)	0.0017 (6)
C4	0.0375 (7)	0.0348 (7)	0.0418 (7)	0.0120 (6)	0.0199 (6)	0.0028 (6)
C5	0.0357 (6)	0.0296 (7)	0.0317 (6)	0.0040 (5)	0.0151 (5)	0.0002 (5)
C6	0.0472 (8)	0.0288 (7)	0.0405 (7)	0.0091 (6)	0.0204 (6)	0.0050 (5)
C7	0.0549 (8)	0.0289 (7)	0.0404 (7)	0.0031 (6)	0.0261 (7)	0.0069 (6)
C8	0.0424 (7)	0.0313 (7)	0.0370 (7)	−0.0009 (5)	0.0236 (6)	0.0002 (5)
C9	0.0341 (6)	0.0284 (6)	0.0351 (6)	0.0029 (5)	0.0187 (5)	0.0014 (5)
C10	0.0295 (6)	0.0273 (6)	0.0294 (6)	0.0003 (5)	0.0135 (5)	−0.0013 (5)
C11	0.0328 (6)	0.0298 (6)	0.0348 (6)	0.0039 (5)	0.0224 (5)	0.0066 (5)
C12	0.0338 (6)	0.0321 (7)	0.0343 (6)	0.0042 (5)	0.0225 (5)	0.0038 (5)
C13	0.0362 (7)	0.0322 (7)	0.0384 (7)	0.0052 (5)	0.0183 (6)	0.0059 (5)
C14	0.0384 (7)	0.0346 (7)	0.0414 (7)	0.0016 (6)	0.0202 (6)	−0.0007 (6)
C15	0.0362 (7)	0.0478 (8)	0.0324 (7)	0.0070 (6)	0.0173 (6)	−0.0004 (6)
C16	0.0454 (8)	0.0399 (8)	0.0365 (7)	0.0133 (6)	0.0200 (6)	0.0082 (6)
C17	0.0424 (7)	0.0316 (7)	0.0370 (7)	0.0052 (5)	0.0225 (6)	0.0043 (5)
C18	0.0363 (7)	0.0267 (6)	0.0374 (7)	0.0074 (5)	0.0193 (5)	0.0051 (5)
C19	0.0397 (7)	0.0320 (7)	0.0430 (7)	0.0040 (5)	0.0256 (6)	0.0001 (5)
C20	0.0358 (7)	0.0344 (7)	0.0519 (8)	0.0027 (6)	0.0215 (6)	−0.0014 (6)
C21	0.0455 (8)	0.0357 (7)	0.0412 (7)	0.0047 (6)	0.0160 (6)	−0.0004 (6)
C22	0.0547 (9)	0.0394 (8)	0.0413 (7)	0.0054 (6)	0.0286 (7)	0.0003 (6)
C23	0.0393 (7)	0.0385 (8)	0.0463 (8)	0.0057 (6)	0.0263 (6)	0.0024 (6)
C24	0.0678 (10)	0.0459 (9)	0.0680 (10)	0.0119 (8)	0.0528 (9)	0.0094 (8)
C25	0.0489 (8)	0.0494 (9)	0.0387 (7)	0.0110 (7)	0.0240 (7)	0.0070 (6)
C26	0.0420 (8)	0.0565 (10)	0.0474 (8)	−0.0107 (7)	0.0259 (7)	−0.0084 (7)
C27	0.0516 (8)	0.0380 (8)	0.0494 (8)	0.0043 (6)	0.0305 (7)	0.0005 (6)

Geometric parameters (Å, º) top

Cl1—C15	1.7357 (15)	C13—H13	0.9500
O1—C2	1.3563 (16)	C14—C15	1.378 (2)
O1—H1	0.89 (2)	C14—H14	0.9500
O2—C8	1.3623 (15)	C15—C16	1.387 (2)
O2—C24	1.4282 (18)	C16—C17	1.384 (2)
N1—C11	1.2744 (17)	C16—H16	0.9500
N1—C18	1.4150 (17)	C17—H17	0.9500
N2—C26	1.4723 (19)	C18—C19	1.3937 (19)
N2—C25	1.4749 (18)	C18—C23	1.3964 (18)
N2—C27	1.4762 (19)	C19—C20	1.378 (2)
C1—C2	1.3828 (17)	C19—H19	0.9500
C1—C10	1.4241 (17)	C20—C21	1.385 (2)
C1—C11	1.5012 (17)	C20—H20	0.9500
C2—C3	1.4119 (19)	C21—C22	1.380 (2)
C3—C4	1.364 (2)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.382 (2)
C4—C5	1.4106 (18)	C22—H22	0.9500
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.4159 (19)	C24—H24A	0.9800
C5—C10	1.4198 (17)	C24—H24B	0.9800
C6—C7	1.360 (2)	C24—H24C	0.9800
C6—H6	0.9500	C25—C26ⁱ	1.540 (2)
C7—C8	1.4154 (19)	C25—H25A	0.9900
C7—H7	0.9500	C25—H25B	0.9900
C8—C9	1.3706 (18)	C26—C25ⁱ	1.540 (2)
C9—C10	1.4221 (17)	C26—H26A	0.9900
C9—H9	0.9500	C26—H26B	0.9900
C11—C12	1.4966 (18)	C27—C27ⁱ	1.545 (3)
C12—C13	1.3931 (19)	C27—H27A	0.9900
C12—C17	1.3949 (18)	C27—H27B	0.9900
C13—C14	1.3890 (19)

C2—O1—H1	110.6 (13)	C16—C15—Cl1	119.57 (11)
C8—O2—C24	116.85 (10)	C17—C16—C15	118.87 (13)
C11—N1—C18	121.58 (11)	C17—C16—H16	120.6
C26—N2—C25	108.56 (12)	C15—C16—H16	120.6
C26—N2—C27	108.21 (12)	C16—C17—C12	120.75 (13)
C25—N2—C27	108.21 (11)	C16—C17—H17	119.6
C2—C1—C10	120.30 (11)	C12—C17—H17	119.6
C2—C1—C11	119.87 (11)	C19—C18—C23	118.91 (13)
C10—C1—C11	119.62 (10)	C19—C18—N1	122.47 (11)
O1—C2—C1	118.17 (11)	C23—C18—N1	118.32 (11)
O1—C2—C3	121.60 (11)	C20—C19—C18	120.01 (12)
C1—C2—C3	120.22 (12)	C20—C19—H19	120.0
C4—C3—C2	120.00 (12)	C18—C19—H19	120.0
C4—C3—H3	120.0	C19—C20—C21	121.01 (13)
C2—C3—H3	120.0	C19—C20—H20	119.5
C3—C4—C5	121.48 (12)	C21—C20—H20	119.5
C3—C4—H4	119.3	C22—C21—C20	119.17 (14)
C5—C4—H4	119.3	C22—C21—H21	120.4
C4—C5—C6	122.23 (12)	C20—C21—H21	120.4
C4—C5—C10	118.96 (12)	C21—C22—C23	120.57 (13)
C6—C5—C10	118.79 (12)	C21—C22—H22	119.7
C7—C6—C5	121.37 (12)	C23—C22—H22	119.7
C7—C6—H6	119.3	C22—C23—C18	120.31 (13)
C5—C6—H6	119.3	C22—C23—H23	119.8
C6—C7—C8	119.72 (12)	C18—C23—H23	119.8
C6—C7—H7	120.1	O2—C24—H24A	109.5
C8—C7—H7	120.1	O2—C24—H24B	109.5
O2—C8—C9	124.82 (12)	H24A—C24—H24B	109.5
O2—C8—C7	114.39 (11)	O2—C24—H24C	109.5
C9—C8—C7	120.79 (12)	H24A—C24—H24C	109.5
C8—C9—C10	120.14 (12)	H24B—C24—H24C	109.5
C8—C9—H9	119.9	N2—C25—C26ⁱ	110.77 (12)
C10—C9—H9	119.9	N2—C25—H25A	109.5
C5—C10—C9	119.01 (11)	C26ⁱ—C25—H25A	109.5
C5—C10—C1	118.81 (11)	N2—C25—H25B	109.5
C9—C10—C1	122.18 (11)	C26ⁱ—C25—H25B	109.5
N1—C11—C12	117.33 (11)	H25A—C25—H25B	108.1
N1—C11—C1	126.31 (12)	N2—C26—C25ⁱ	110.40 (11)
C12—C11—C1	116.14 (11)	N2—C26—H26A	109.6
C13—C12—C17	118.81 (12)	C25ⁱ—C26—H26A	109.6
C13—C12—C11	120.47 (11)	N2—C26—H26B	109.6
C17—C12—C11	120.62 (12)	C25ⁱ—C26—H26B	109.6
C14—C13—C12	121.12 (13)	H26A—C26—H26B	108.1
C14—C13—H13	119.4	N2—C27—C27ⁱ	110.45 (7)
C12—C13—H13	119.4	N2—C27—H27A	109.6
C15—C14—C13	118.53 (13)	C27ⁱ—C27—H27A	109.6
C15—C14—H14	120.7	N2—C27—H27B	109.6
C13—C14—H14	120.7	C27ⁱ—C27—H27B	109.6
C14—C15—C16	121.86 (13)	H27A—C27—H27B	108.1
C14—C15—Cl1	118.57 (12)

C10—C1—C2—O1	−179.95 (12)	C2—C1—C11—C12	81.97 (15)
C11—C1—C2—O1	5.43 (19)	C10—C1—C11—C12	−92.69 (13)
C10—C1—C2—C3	−0.9 (2)	N1—C11—C12—C13	−147.08 (12)
C11—C1—C2—C3	−175.50 (12)	C1—C11—C12—C13	27.86 (16)
O1—C2—C3—C4	−177.23 (13)	N1—C11—C12—C17	29.38 (16)
C1—C2—C3—C4	3.7 (2)	C1—C11—C12—C17	−155.68 (11)
C2—C3—C4—C5	−2.2 (2)	C17—C12—C13—C14	−2.25 (18)
C3—C4—C5—C6	179.21 (14)	C11—C12—C13—C14	174.28 (11)
C3—C4—C5—C10	−2.1 (2)	C12—C13—C14—C15	1.67 (19)
C4—C5—C6—C7	175.43 (14)	C13—C14—C15—C16	0.5 (2)
C10—C5—C6—C7	−3.2 (2)	C13—C14—C15—Cl1	−179.35 (10)
C5—C6—C7—C8	−0.4 (2)	C14—C15—C16—C17	−2.0 (2)
C24—O2—C8—C9	−5.2 (2)	Cl1—C15—C16—C17	177.82 (10)
C24—O2—C8—C7	174.25 (14)	C15—C16—C17—C12	1.4 (2)
C6—C7—C8—O2	−175.83 (13)	C13—C12—C17—C16	0.67 (18)
C6—C7—C8—C9	3.7 (2)	C11—C12—C17—C16	−175.85 (11)
O2—C8—C9—C10	176.23 (12)	C11—N1—C18—C19	59.63 (17)
C7—C8—C9—C10	−3.2 (2)	C11—N1—C18—C23	−126.69 (13)
C4—C5—C10—C9	−175.10 (12)	C23—C18—C19—C20	−1.1 (2)
C6—C5—C10—C9	3.62 (18)	N1—C18—C19—C20	172.57 (12)
C4—C5—C10—C1	4.86 (18)	C18—C19—C20—C21	1.4 (2)
C6—C5—C10—C1	−176.42 (12)	C19—C20—C21—C22	−0.4 (2)
C8—C9—C10—C5	−0.45 (19)	C20—C21—C22—C23	−0.9 (2)
C8—C9—C10—C1	179.60 (12)	C21—C22—C23—C18	1.2 (2)
C2—C1—C10—C5	−3.40 (18)	C19—C18—C23—C22	−0.2 (2)
C11—C1—C10—C5	171.24 (11)	N1—C18—C23—C22	−174.12 (12)
C2—C1—C10—C9	176.56 (12)	C26—N2—C25—C26ⁱ	−56.40 (14)
C11—C1—C10—C9	−8.81 (18)	C27—N2—C25—C26ⁱ	60.82 (16)
C18—N1—C11—C12	179.94 (11)	C25—N2—C26—C25ⁱ	60.43 (14)
C18—N1—C11—C1	5.59 (18)	C27—N2—C26—C25ⁱ	−56.79 (16)
C2—C1—C11—N1	−103.62 (15)	C26—N2—C27—C27ⁱ	61.24 (19)
C10—C1—C11—N1	81.72 (16)	C25—N2—C27—C27ⁱ	−56.21 (19)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱⁱ	0.89 (2)	1.86 (2)	2.7401 (18)	167.2 (18)
C20—H20···Cl1ⁱⁱⁱ	0.95	2.78	3.6071 (17)	146

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈ClNO₂·0.5C₆H₁₂N₂
M_r	443.93
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	25.0027 (5), 9.92298 (18), 20.0052 (4)
β (°)	114.621 (1)
V (Å³)	4512.07 (16)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.71
Crystal size (mm)	0.60 × 0.50 × 0.40

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.381, 0.548
No. of measured, independent and observed [I > 2σ(I)] reflections	39753, 4125, 3831
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.04
No. of reflections	4125
No. of parameters	295
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.32

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.89 (2)	1.86 (2)	2.7401 (18)	167.2 (18)
C20—H20···Cl1ⁱⁱ	0.95	2.78	3.6071 (17)	146

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi for technical advice.

References

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hijikata, D., Nakaema, K., Watanabe, S., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o554. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o2497. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o403. Web of Science CSD CrossRef IUCr Journals Google Scholar
Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2498

doi:10.1107/S1600536810034690

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

1-[(4-Chloro­phen­yl)(phenyl­imino)­meth­yl]-7-meth­­oxy-2-naphthol–1,4-di­aza­bi­cyclo­[2.2.2]octane (2/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)