3-(4-Chloro­benzo­yl)-4-(4-chloro­phen­yl)-1-phenethyl­piperidin-4-ol

Aydın, A.; Akkurt, M.; Mete, E.; Sahin, E.; Gul, H.I.

doi:10.1107/S1600536811018034

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1447-o1448

doi:10.1107/S1600536811018034

Open

access

3-(4-Chlorobenzoyl)-4-(4-chlorophenyl)-1-phenethylpiperidin-4-ol

Abdullah Aydın,^a ^* Mehmet Akkurt,^b Ebru Mete,^c Ertan Sahin ^c and Halise Inci Gul ^d

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, and ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, 25240 Erzurum, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

(Received 22 April 2011; accepted 12 May 2011; online 20 May 2011)

In the title compound, C₂₆H₂₅Cl₂NO₂, the piperidine ring adopts a chair conformation with a cis configuration of the carbonyl and hydroxy substituents. The dihedral angle between the aromatic rings of the chlorobenzene groups is 24.3 (2)°. The phenyl ring forms dihedral angles of 59.4 (3) and 44.1 (3)° with the benzene rings. In the crystal, molecules are linked by intermolecular O—H⋯N and C—H⋯O hydrogen bonds and C—H⋯π interactions into layers parallel to the bc plane.

Related literature

For the synthesis and biological activity of Mannich bases, see: Dimmock et al. (1991 ); Dimmock & Kumar (1997); Gul et al. (2001 , 2004 , 2005 ); Atwal et al. (1969 ); Gul (2005 ); Erciyas et al. (1994 ); Porretta et al. (1995 ); Piscopo et al. (1986 ); Manavathu et al. (1998 ); Vashishtha et al. (1998 ); Canturk et al. (2008 ); Suleyman et al. (2007 ); Yogeeswari et al. (2005 ); Mete et al. (2010a ,b ) For MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985 ); Stewart (1993 ). For bond-length data, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₅Cl₂NO₂
M_r = 454.37
Monoclinic, P 2₁ /c
a = 16.950 (4) Å
b = 12.863 (3) Å
c = 10.792 (2) Å
β = 97.779 (13)°
V = 2331.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 294 K
0.23 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan [XABS2 (Parkin et al., 1995 ); cubic fit to sin(θ)/λ, 24 parameters] T_min = 0.934, T_max = 0.965
4830 measured reflections
4830 independent reflections
1939 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.148
S = 1.07
4830 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C15–C20 and C21–C26 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.82	2.11	2.879 (5)	155
C13—H13B⋯O2ⁱⁱ	0.97	2.54	3.372 (5)	144
C2—H2⋯Cg2ⁱⁱⁱ	0.93	2.85	3.739 (9)	159
C16—H16⋯Cg3^iv	0.93	2.85	3.646 (5)	144
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018034/rz2590sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018034/rz2590Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018034/rz2590Isup3.cml

checkCIF report

Comment top

The title compound, C₂₆H₂₅Cl₂NO₂, is a semicyclic mono Mannich base. Mannich bases are generally formed by the reaction between a compound containing reactive hydrogen atom, formaldehyde, and a secondary amine. On occasion, aldehydes other than formaldehyde may be employed, and the secondary amine may be replaced by ammonia and primary amines. The process whereby these compounds are formed is known as the Mannich reaction (Dimmock & Kumar, 1997).

Mannich bases have several biological activities such as antimicrobial (Gul et al., 2001, Gul, 2005; Erciyas et al., 1994; Porretta et al., 1995; Piscopo et al., 1986; Manavathu et al., 1998; Vashishtha et al., 1998), analgesic (Atwal et al., 1969), anti-inflammatory (Gul, 2005; Suleyman et al., 2007) and anticonvulsant activities (Gul et al., 2004; Dimmock et al., 1991). Considerable anticancer activity was also attributed to Mannich bases (Dimmock & Kumar, 1997). It has been reported that these compounds have an inhibiting effect on DNA topoisomerase I (Canturk et al., 2008) and II (Yogeeswari et al., 2005).

The biological activities of Mannich bases were attributed to the thiol alkylation of α,β-unsaturated ketones produced from Mannich bases. Mannich bases which have at least one activated hydrogen atom at the β-position of amine can undergo deamination under simulated physiological condition in vitro or in vivo condition to produce α,β-unsaturated ketones which are biologically active species (Gul et al., 2005).

The title compound was tested against seven types of plant pathogenic fungi and three types of human pathogenic fungi using the agar dilution assay (Mete et al., 2010b). Cytotoxic activity of the title compound against androgen-independent prostate cancer cells (PC-3) and the biological activity on DNA topoisomerase I enzyme were also reported (Mete et al., 2010a).

The molecular structure of the title compound, (I), is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are in normal ranges. The piperidine ring (N1/C9–C13) adopts a chair conformation [puckering parameters are Q_T = 0.590 (4) Å, θ = 4.4 (4) °, ϕ = 289 (5) ° (Cremer & Pople, 1975)], with atoms C9, C10, C12 and C13 occupying coplanar positions and atoms C11 and N1 on opposite sides of the plane. The carbonyl and hydroxy groups are cis configured. The C15–C20 and C21–C26 benzene rings form a dihedral angle of 24.3 (2)° with each other. The C1–C6 phenyl ring forms dihedral angles of 59.4 (3) and 44.1 (3)° with the C15–C20 and C21–C26 benzene rings, respectively. The crystal structure is stabilized by intermolecular O—H···N and C—H···O hydrogen bonds (Table 1, Fig. 2) and C—H···π interactions (Table 1), forming layer parallel to the bc plane.

We applied a semiempirical calculation AM1 of (I) with MOPAC (Dewar et al., 1985; Stewart, 1993). Figure 3 shows the conformation of the calculated molecule. The values of the structural parameters of (I) obtained by the results of the theoretical calculations (based on isolated molecules) and X-ray structural determinations in the solid state are almost identical within experimental error. The dihedral angles between the mean planes of the aromatic rings in (I) are listed in Table 2 for comparision. The calculated dipole moment of (I) is 2.119 D. The HOMO and LUMO energy levels are -9.22109 and -0.56402 eV, respectively. We may state that the theoretical calculation of (I) supports the suggestion that the present intermolecular interactions in (I) influence crystal packing.

Related literature top

For the synthesis and biological activity of Mannich bases, see: Dimmock et al. (1991); Dimmock & Kumar (1997); Gul et al. (2001, 2004, 2005); Atwal et al. (1969); Gul (2005); Erciyas et al. (1994); Porretta et al. (1995); Piscopo et al. (1986); Manavathu et al. (1998); Vashishtha et al. (1998); Canturk et al. (2008); Suleyman et al. (2007); Yogeeswari et al. (2005); Mete et al. (2010a,b) For MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985); Stewart (1993). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

4'-Chloroacetophenone (10.00 g), paraformaldehyde (1.95 g) and phenylethylamine hydrochloride (5.12 g) in the molar ratio 2:2:1 were stirred and heated in an oil bath. When the temperature reached 365 K, the solid mixture started to melt. When heating continued, the reaction content solidified again totally. The reaction flask was quickly removed from the oil bath. The temperature of the reaction medium spontaneously increased to 377 K. Following the increase in temperature and removal of the flask from the oil bath, ethyl acetate (20 ml) was added to the reaction flask when the temperature had dropped to 338 K. Stirring was continued for 24 h. The formed precipitate was separated by filtration and crystallized from ethanol to obtain 1-(4-chlorophenyl)-3-phenethylamino-1-propanone hydrochloride. The ethyl acetate present in the reaction flask was removed under reduced pressure to obtain the title compound (I) as a viscous orange oil. The compound was purified by column chromatography using a basic Al₂O₃ column with ethyl acetate/hexane (1:9 v/v) as eluent (yield 18%; m. p. 405–407 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution. ¹H-NMR(DMSO) δ: 1.55 (br d, 1H, J = 13.6 Hz), 2.04–2.11 (m, 1H), 2.56–2.91 (m, 8H), 4.30 (dd, 1H, J = 11.0, 3.7 Hz), 4.96 (d, OH, J = 1.1 Hz), 7.15 (quasi d,2H, J = 8.8 Hz), 7.21–7.28 (m, 5H), 7.43 (quasi d, 2H, J = 8.8 Hz), 7.50 (quasi d, 2H, J = 8.4 Hz), 7.74 (quasi d, 2H, J = 8.8 Hz). ¹³C-NMR(DMSO) δ: 33.5, 39.6, 48.9, 51.3, 52.3, 60.2, 73.1, 126.5, 127.7, 128.3, 128.9, 129.3, 129.4, 130.7, 131.8, 136.0, 138.9, 141.1, 147.2, 202.5. Elemental analysis: C₂₆H₂₅Cl₂NO₂, Calc.(%) / Found (%): C: 68.72/68.76, H: 5.55/5.43, N: 3.08/3.27 (Mete et al., 2010b).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound viewed down the a axis. H atoms not involved in hydrogen bonds (dashed lines) are omitted for clarity.
	Fig. 3. A spatial view of the calculated molecule of the title compound.

3-(4-Chlorobenzoyl)-4-(4-chlorophenyl)-1-phenethylpiperidin-4-ol top

Crystal data top

C₂₆H₂₅Cl₂NO₂	F(000) = 952
M_r = 454.37	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5626 reflections
a = 16.950 (4) Å	θ = 2.4–30.5°
b = 12.863 (3) Å	µ = 0.30 mm⁻¹
c = 10.792 (2) Å	T = 294 K
β = 97.779 (13)°	Block, colourless
V = 2331.3 (9) Å³	0.23 × 0.14 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4830 independent reflections
Radiation source: Sealed Tube	1939 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.000
Detector resolution: 10.00 pixels mm^-1	θ_max = 26.5°, θ_min = 2.4°
dtprofit.ref scans	h = −21→21
Absorption correction: multi-scan [XABS2 (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters]	k = 0→16
T_min = 0.934, T_max = 0.965	l = 0→13
4830 measured reflections

Refinement top

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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0094P)² + 1.4373P] where P = (F_o² + 2F_c²)/3
4830 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₆H₂₅Cl₂NO₂	V = 2331.3 (9) Å³
M_r = 454.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.950 (4) Å	µ = 0.30 mm⁻¹
b = 12.863 (3) Å	T = 294 K
c = 10.792 (2) Å	0.23 × 0.14 × 0.12 mm
β = 97.779 (13)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4830 independent reflections
Absorption correction: multi-scan [XABS2 (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters]	1939 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.965	R_int = 0.000
4830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
4830 reflections	Δρ_min = −0.13 e Å⁻³
282 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.45921 (10)	0.30278 (16)	0.49332 (19)	0.1484 (10)
Cl2	0.47453 (11)	0.57277 (17)	0.1905 (2)	0.1803 (13)
O1	0.0660 (2)	0.3454 (2)	0.3384 (3)	0.0716 (12)
O2	0.08304 (19)	0.5228 (2)	0.1541 (3)	0.0769 (14)
N1	−0.0050 (2)	0.2257 (3)	0.0508 (3)	0.0590 (16)
C1	−0.1997 (4)	0.1029 (5)	−0.2619 (7)	0.112 (3)
C2	−0.2733 (7)	0.1035 (6)	−0.3331 (8)	0.146 (5)
C3	−0.3396 (5)	0.1102 (6)	−0.2802 (11)	0.136 (5)
C4	−0.3367 (5)	0.1168 (5)	−0.1543 (9)	0.128 (4)
C5	−0.2612 (4)	0.1186 (5)	−0.0817 (6)	0.106 (3)
C6	−0.1933 (3)	0.1121 (4)	−0.1342 (6)	0.074 (2)
C7	−0.1130 (3)	0.1128 (4)	−0.0571 (5)	0.089 (3)
C8	−0.0868 (3)	0.2217 (3)	−0.0146 (4)	0.0683 (17)
C9	0.0000 (3)	0.1708 (4)	0.1714 (4)	0.0685 (17)
C10	0.0822 (3)	0.1743 (3)	0.2431 (4)	0.0651 (17)
C11	0.1144 (3)	0.2856 (3)	0.2674 (4)	0.0601 (17)
C12	0.1052 (2)	0.3410 (3)	0.1367 (4)	0.0521 (17)
C13	0.0195 (2)	0.3339 (3)	0.0750 (4)	0.0598 (17)
C14	0.1317 (3)	0.4537 (4)	0.1482 (4)	0.0581 (17)
C15	0.2176 (3)	0.4812 (4)	0.1536 (4)	0.0581 (17)
C16	0.2732 (3)	0.4180 (4)	0.1104 (4)	0.070 (2)
C17	0.3525 (3)	0.4459 (4)	0.1192 (5)	0.089 (2)
C18	0.3752 (3)	0.5378 (5)	0.1759 (6)	0.096 (3)
C19	0.3223 (4)	0.6037 (4)	0.2184 (6)	0.102 (3)
C20	0.2425 (3)	0.5758 (4)	0.2084 (5)	0.082 (3)
C21	0.2001 (3)	0.2836 (4)	0.3290 (4)	0.0582 (17)
C22	0.2562 (3)	0.2166 (4)	0.2909 (4)	0.0733 (19)
C23	0.3354 (3)	0.2222 (4)	0.3407 (5)	0.087 (3)
C24	0.3593 (3)	0.2945 (5)	0.4313 (5)	0.084 (2)
C25	0.3063 (4)	0.3599 (4)	0.4732 (5)	0.085 (3)
C26	0.2267 (3)	0.3553 (4)	0.4218 (4)	0.0694 (19)
H1	−0.15410	0.09610	−0.30030	0.1340*
H1A	0.05700	0.31190	0.39960	0.1070*
H2	−0.27690	0.09920	−0.41970	0.1750*
H3	−0.38870	0.11030	−0.33040	0.1630*
H4	−0.38300	0.12010	−0.11710	0.1540*
H5	−0.25790	0.12430	0.00480	0.1270*
H7A	−0.07430	0.08360	−0.10570	0.1070*
H7B	−0.11450	0.06910	0.01580	0.1070*
H8A	−0.09080	0.26700	−0.08710	0.0820*
H8B	−0.12280	0.24810	0.04060	0.0820*
H9A	−0.01560	0.09880	0.15630	0.0820*
H9B	−0.03720	0.20210	0.22140	0.0820*
H10A	0.11810	0.13630	0.19680	0.0780*
H10B	0.08170	0.13950	0.32260	0.0780*
H12	0.13890	0.30470	0.08370	0.0620*
H13A	−0.01500	0.36600	0.12880	0.0720*
H13B	0.01370	0.37200	−0.00330	0.0720*
H16	0.25700	0.35460	0.07420	0.0840*
H17	0.38920	0.40320	0.08740	0.1060*
H19	0.33930	0.66710	0.25400	0.1220*
H20	0.20580	0.62000	0.23810	0.0990*
H22	0.24010	0.16680	0.23040	0.0880*
H23	0.37230	0.17720	0.31310	0.1040*
H25	0.32310	0.40760	0.53590	0.1020*
H26	0.19060	0.40100	0.45010	0.0830*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0835 (12)	0.1827 (19)	0.1682 (18)	−0.0113 (12)	−0.0226 (11)	−0.0167 (15)
Cl2	0.1017 (14)	0.190 (2)	0.243 (3)	−0.0701 (14)	0.0008 (15)	−0.0200 (18)
O1	0.086 (2)	0.076 (2)	0.058 (2)	0.0178 (19)	0.0290 (18)	0.0100 (17)
O2	0.084 (2)	0.063 (2)	0.085 (3)	0.0156 (19)	0.016 (2)	−0.0046 (19)
N1	0.063 (3)	0.059 (3)	0.056 (2)	−0.004 (2)	0.012 (2)	0.005 (2)
C1	0.121 (6)	0.112 (5)	0.103 (6)	−0.018 (4)	0.016 (5)	−0.025 (4)
C2	0.192 (10)	0.118 (6)	0.113 (7)	−0.012 (7)	−0.033 (8)	−0.029 (5)
C3	0.104 (7)	0.109 (6)	0.184 (10)	−0.020 (5)	−0.020 (7)	0.010 (7)
C4	0.100 (6)	0.117 (6)	0.171 (8)	−0.004 (4)	0.032 (6)	0.036 (6)
C5	0.076 (4)	0.131 (6)	0.112 (5)	−0.012 (4)	0.014 (4)	0.029 (4)
C6	0.077 (4)	0.067 (3)	0.079 (4)	−0.016 (3)	0.014 (4)	0.001 (3)
C7	0.078 (4)	0.074 (4)	0.114 (5)	−0.015 (3)	0.006 (4)	−0.002 (3)
C8	0.070 (3)	0.066 (3)	0.070 (3)	−0.001 (3)	0.013 (3)	0.005 (3)
C9	0.076 (3)	0.065 (3)	0.067 (3)	−0.003 (3)	0.019 (3)	0.014 (3)
C10	0.073 (3)	0.060 (3)	0.064 (3)	0.003 (3)	0.015 (3)	0.010 (3)
C11	0.070 (3)	0.063 (3)	0.049 (3)	0.012 (3)	0.014 (3)	0.002 (3)
C12	0.059 (3)	0.050 (3)	0.049 (3)	0.001 (2)	0.014 (2)	0.000 (2)
C13	0.068 (3)	0.059 (3)	0.054 (3)	0.003 (2)	0.014 (2)	0.002 (2)
C14	0.074 (3)	0.057 (3)	0.045 (3)	−0.003 (3)	0.014 (2)	0.002 (2)
C15	0.069 (3)	0.051 (3)	0.053 (3)	−0.007 (3)	0.004 (3)	0.010 (2)
C16	0.061 (3)	0.073 (4)	0.076 (4)	−0.005 (3)	0.007 (3)	−0.002 (3)
C17	0.073 (4)	0.094 (4)	0.098 (4)	−0.016 (3)	0.010 (3)	−0.004 (4)
C18	0.079 (4)	0.092 (5)	0.109 (5)	−0.025 (4)	−0.014 (4)	0.008 (4)
C19	0.118 (6)	0.068 (4)	0.112 (5)	−0.031 (4)	−0.013 (4)	−0.004 (4)
C20	0.101 (5)	0.061 (4)	0.082 (4)	−0.007 (3)	0.003 (3)	0.004 (3)
C21	0.071 (3)	0.060 (3)	0.044 (3)	0.009 (3)	0.009 (2)	0.006 (2)
C22	0.064 (3)	0.085 (4)	0.070 (3)	0.010 (3)	0.006 (3)	−0.010 (3)
C23	0.071 (4)	0.101 (5)	0.088 (4)	0.018 (3)	0.006 (3)	−0.007 (4)
C24	0.066 (4)	0.091 (4)	0.091 (4)	0.000 (3)	−0.002 (3)	0.008 (4)
C25	0.098 (5)	0.078 (4)	0.075 (4)	0.000 (3)	−0.004 (4)	−0.001 (3)
C26	0.087 (4)	0.063 (3)	0.060 (3)	0.012 (3)	0.017 (3)	0.006 (3)

Geometric parameters (Å, º) top

Cl1—C24	1.738 (5)	C21—C22	1.386 (7)
Cl2—C18	1.729 (6)	C22—C23	1.379 (7)
O1—C11	1.422 (6)	C23—C24	1.370 (8)
O2—C14	1.220 (6)	C24—C25	1.353 (8)
O1—H1A	0.8200	C25—C26	1.389 (8)
N1—C9	1.473 (6)	C1—H1	0.9300
N1—C13	1.466 (5)	C2—H2	0.9300
N1—C8	1.469 (6)	C3—H3	0.9300
C1—C2	1.374 (13)	C4—H4	0.9300
C1—C6	1.373 (10)	C5—H5	0.9300
C2—C3	1.330 (15)	C7—H7A	0.9700
C3—C4	1.356 (15)	C7—H7B	0.9700
C4—C5	1.407 (11)	C8—H8A	0.9700
C5—C6	1.352 (9)	C8—H8B	0.9700
C6—C7	1.496 (8)	C9—H9A	0.9700
C7—C8	1.521 (7)	C9—H9B	0.9700
C9—C10	1.500 (7)	C10—H10A	0.9700
C10—C11	1.542 (6)	C10—H10B	0.9700
C11—C12	1.569 (6)	C12—H12	0.9800
C11—C21	1.514 (7)	C13—H13A	0.9700
C12—C14	1.518 (6)	C13—H13B	0.9700
C12—C13	1.517 (5)	C16—H16	0.9300
C14—C15	1.492 (7)	C17—H17	0.9300
C15—C16	1.373 (7)	C19—H19	0.9300
C15—C20	1.393 (7)	C20—H20	0.9300
C16—C17	1.382 (7)	C22—H22	0.9300
C17—C18	1.362 (8)	C23—H23	0.9300
C18—C19	1.358 (8)	C25—H25	0.9300
C19—C20	1.389 (8)	C26—H26	0.9300
C21—C26	1.391 (7)

C11—O1—H1A	109.00	C3—C2—H2	119.00
C8—N1—C9	110.2 (3)	C2—C3—H3	119.00
C8—N1—C13	110.2 (3)	C4—C3—H3	119.00
C9—N1—C13	108.5 (3)	C3—C4—H4	121.00
C2—C1—C6	120.2 (7)	C5—C4—H4	121.00
C1—C2—C3	121.1 (9)	C4—C5—H5	119.00
C2—C3—C4	121.1 (9)	C6—C5—H5	119.00
C3—C4—C5	117.8 (8)	C6—C7—H7A	109.00
C4—C5—C6	121.8 (7)	C6—C7—H7B	109.00
C1—C6—C5	118.0 (6)	C8—C7—H7A	109.00
C1—C6—C7	120.1 (5)	C8—C7—H7B	109.00
C5—C6—C7	121.9 (6)	H7A—C7—H7B	108.00
C6—C7—C8	112.3 (4)	N1—C8—H8A	109.00
N1—C8—C7	113.3 (4)	N1—C8—H8B	109.00
N1—C9—C10	112.3 (4)	C7—C8—H8A	109.00
C9—C10—C11	113.5 (4)	C7—C8—H8B	109.00
O1—C11—C10	112.2 (4)	H8A—C8—H8B	108.00
O1—C11—C12	104.1 (3)	N1—C9—H9A	109.00
C10—C11—C12	106.2 (3)	N1—C9—H9B	109.00
C10—C11—C21	110.8 (4)	C10—C9—H9A	109.00
C12—C11—C21	112.0 (4)	C10—C9—H9B	109.00
O1—C11—C21	111.2 (4)	H9A—C9—H9B	108.00
C11—C12—C13	109.9 (3)	C9—C10—H10A	109.00
C11—C12—C14	111.6 (3)	C9—C10—H10B	109.00
C13—C12—C14	110.4 (3)	C11—C10—H10A	109.00
N1—C13—C12	111.5 (3)	C11—C10—H10B	109.00
O2—C14—C12	120.4 (4)	H10A—C10—H10B	108.00
C12—C14—C15	120.4 (4)	C11—C12—H12	108.00
O2—C14—C15	119.2 (4)	C13—C12—H12	108.00
C14—C15—C16	123.9 (5)	C14—C12—H12	108.00
C14—C15—C20	117.5 (4)	N1—C13—H13A	109.00
C16—C15—C20	118.6 (5)	N1—C13—H13B	109.00
C15—C16—C17	121.9 (5)	C12—C13—H13A	109.00
C16—C17—C18	118.0 (5)	C12—C13—H13B	109.00
Cl2—C18—C19	119.1 (5)	H13A—C13—H13B	108.00
C17—C18—C19	122.3 (5)	C15—C16—H16	119.00
Cl2—C18—C17	118.6 (4)	C17—C16—H16	119.00
C18—C19—C20	119.5 (5)	C16—C17—H17	121.00
C15—C20—C19	119.6 (5)	C18—C17—H17	121.00
C11—C21—C26	120.2 (4)	C18—C19—H19	120.00
C22—C21—C26	117.2 (5)	C20—C19—H19	120.00
C11—C21—C22	122.4 (4)	C15—C20—H20	120.00
C21—C22—C23	121.5 (5)	C19—C20—H20	120.00
C22—C23—C24	119.5 (5)	C21—C22—H22	119.00
Cl1—C24—C23	119.7 (4)	C23—C22—H22	119.00
Cl1—C24—C25	119.3 (5)	C22—C23—H23	120.00
C23—C24—C25	121.0 (5)	C24—C23—H23	120.00
C24—C25—C26	119.6 (5)	C24—C25—H25	120.00
C21—C26—C25	121.2 (5)	C26—C25—H25	120.00
C2—C1—H1	120.00	C21—C26—H26	119.00
C6—C1—H1	120.00	C25—C26—H26	119.00
C1—C2—H2	120.00

C9—N1—C13—C12	62.1 (4)	C10—C11—C12—C14	177.6 (4)
C9—N1—C8—C7	−67.4 (5)	C14—C12—C13—N1	174.0 (3)
C13—N1—C8—C7	173.0 (4)	C11—C12—C14—O2	−96.0 (5)
C8—N1—C13—C12	−177.2 (3)	C13—C12—C14—O2	26.5 (6)
C13—N1—C9—C10	−58.3 (5)	C13—C12—C14—C15	−154.0 (4)
C8—N1—C9—C10	−179.0 (4)	C11—C12—C14—C15	83.5 (5)
C2—C1—C6—C7	−179.2 (6)	C11—C12—C13—N1	−62.5 (4)
C6—C1—C2—C3	−1.8 (11)	O2—C14—C15—C16	−159.1 (4)
C2—C1—C6—C5	1.9 (9)	O2—C14—C15—C20	22.4 (6)
C1—C2—C3—C4	0.1 (12)	C12—C14—C15—C16	21.5 (6)
C2—C3—C4—C5	1.4 (11)	C12—C14—C15—C20	−157.1 (4)
C3—C4—C5—C6	−1.2 (10)	C14—C15—C16—C17	−178.9 (4)
C4—C5—C6—C1	−0.4 (9)	C20—C15—C16—C17	−0.4 (7)
C4—C5—C6—C7	−179.3 (5)	C14—C15—C20—C19	178.4 (5)
C1—C6—C7—C8	102.4 (6)	C16—C15—C20—C19	−0.2 (7)
C5—C6—C7—C8	−78.7 (6)	C15—C16—C17—C18	1.9 (8)
C6—C7—C8—N1	−174.4 (4)	C16—C17—C18—Cl2	178.8 (4)
N1—C9—C10—C11	56.4 (5)	C16—C17—C18—C19	−2.9 (9)
C9—C10—C11—C12	−52.7 (5)	Cl2—C18—C19—C20	−179.3 (5)
C9—C10—C11—C21	−174.6 (4)	C17—C18—C19—C20	2.4 (10)
C9—C10—C11—O1	60.4 (5)	C18—C19—C20—C15	−0.8 (9)
C10—C11—C12—C13	54.7 (4)	C11—C21—C22—C23	174.2 (4)
O1—C11—C12—C13	−63.8 (4)	C26—C21—C22—C23	−1.5 (7)
O1—C11—C12—C14	59.0 (4)	C11—C21—C26—C25	−175.3 (4)
C21—C11—C12—C14	−61.3 (5)	C22—C21—C26—C25	0.5 (7)
O1—C11—C21—C22	168.5 (4)	C21—C22—C23—C24	1.0 (8)
O1—C11—C21—C26	−16.0 (6)	C22—C23—C24—Cl1	−179.4 (4)
C10—C11—C21—C22	43.0 (6)	C22—C23—C24—C25	0.5 (8)
C10—C11—C21—C26	−141.5 (4)	Cl1—C24—C25—C26	178.5 (4)
C12—C11—C21—C22	−75.4 (5)	C23—C24—C25—C26	−1.4 (8)
C12—C11—C21—C26	100.1 (5)	C24—C25—C26—C21	0.9 (8)
C21—C11—C12—C13	175.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C15–C20 and C21–C26 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.11	2.879 (5)	155
C13—H13B···O2ⁱⁱ	0.97	2.54	3.372 (5)	144
C2—H2···Cg2ⁱⁱⁱ	0.93	2.85	3.739 (9)	159
C16—H16···Cg3^iv	0.93	2.85	3.646 (5)	144

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅Cl₂NO₂
M_r	454.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	16.950 (4), 12.863 (3), 10.792 (2)
β (°)	97.779 (13)
V (Å³)	2331.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.23 × 0.14 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan [XABS2 (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters]
T_min, T_max	0.934, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	4830, 4830, 1939
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.148, 1.07
No. of reflections	4830
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C15–C20 and C21–C26 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.11	2.879 (5)	155
C13—H13B···O2ⁱⁱ	0.97	2.54	3.372 (5)	144
C2—H2···Cg2ⁱⁱⁱ	0.93	2.85	3.739 (9)	159
C16—H16···Cg3^iv	0.93	2.85	3.646 (5)	144

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

Dihedral angles (°) between the mean planes of the aromatic rings top

	X-ray	AM1	X-ray	AM1
	Ring-2	Ring-2	Ring-3	Ring-3
Ring-1	59.5 (3)	69.47	44.2 (3)	89.21
Ring-2			24.4 (3)	28.56

Ring-1 is the C1–C6 phenyl ring, Ring-2 is the C15–C20 benzene ring and Ring-3 is the C21–C26 benzene ring.

Acknowledgements

The authors are indebted to the Department of Chemistry, Ataturk University, Erzurum, Turkey, for use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund. In addition, this work was partly supported by a grant from the Ataturk University Research Fund (project No. 2006/96).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Atwal, M. S., Bauer, L., Dixit, S. N., Gearien, J. E., Megahy, M., Morris, R. & Pokorny, C. (1969). J. Med. Chem. 12, 994–997. CrossRef CAS PubMed Web of Science Google Scholar
Canturk, P., Kucukoglu, K., Topcu, Z., Gul, M. & Gul, H. I. (2008). Arzneim. Forschung. (Drug Res.), 58, 686–691. CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dewar, M. J. S., Zoebish, E. G., Healy, E. F. & Stewart, J. J. P. (1985). J. Am. Chem. Soc. 107, 3902–3909. CrossRef CAS Web of Science Google Scholar
Dimmock, J. R. & Kumar, P. (1997). Curr. Med. Chem. 4, 1–22. CAS Google Scholar
Dimmock, J. R., Patil, S. A. & Shyam, K. (1991). Pharmazie, 46, 538–539. PubMed CAS Web of Science Google Scholar
Erciyas, E., Erkaleli, H. I. & Cosar, G. (1994). J. Pharm. Sci. 83, 545–548. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gul, M. (2005). PhD thesis, University of Kuopio, Finland. Google Scholar
Gul, M., Atalay, M., Gul, H. I., Nakao, C., Lappalainen, J. & Hanninen, O. (2005). Toxicol. in Vitro, 19, 573–580. Web of Science CrossRef PubMed CAS Google Scholar
Gul, H. I., Calis, U. & Vepsalainen, J. (2004). Arzneim. Forschung. (Drug Res.), 54, 359–364. CAS Google Scholar
Gul, H. I., Ojanen, T., Vepsalainen, J., Gul, M., Erciyas, E. & Hanninen, O. (2001). Arzneim. Forschung. (Drug Res.), 51, 72–75. CAS Google Scholar
Manavathu, E. K., Vashishtha, S. C., Alangaden, G. J. & Dimmock, J. R. (1998). Can. J. Microbiol. 44, 74–79. Web of Science CrossRef CAS PubMed Google Scholar
Mete, E., Gul, H. I., Canturk, P., Topcu, Z., Pandit, B., Gul, M. & Li, P. K. (2010a). Z. Naturforsch. Teil C, 65, 647–652. CAS Google Scholar
Mete, E., Ozelgul, C., Kazaz, C., Yurdakul, D., Sahin, F. & Gul, H. I. (2010b). Arch. Pharm. Chem. Life Sci. 343, 291–300. CAS Google Scholar
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56. CrossRef CAS Web of Science IUCr Journals Google Scholar
Piscopo, E., Diurno, M. V., Imperadrice, F. & Caliendo, V. (1986). Boll. Soc. Ital. Biol. Sper. 62, 1449–1455. CAS PubMed Google Scholar
Porretta, G. C., Biava, M., Fioravanti, R., Fischetti, M., Boccia, R., Villa, A. & Simonetti, N. (1995). IFarmaco, 50, 617–623. CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stewart, J. J. P. (1993). MOPAC7.0. QCPE Program No. 455. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN, USA. Google Scholar
Suleyman, H., Gul, H. I., Gul, M., Alkan, M. & Gocer, F. (2007). Biol. Pharm. Bull. 30, 63–67. Web of Science CrossRef PubMed CAS Google Scholar
Vashishtha, S. C., Dimmock, J. R. & Manavathu, E. K. (1998). Pharmazie, 53, 499–500. Web of Science CAS PubMed Google Scholar
Yogeeswari, P., Sriram, D., Kavya, R. & Tiwari, S. (2005). Biomed. Pharmacother. 59, 501–510. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1447-o1448

doi:10.1107/S1600536811018034

Open

access