(E)-3-(4-Meth­oxy­phen­yl)-1-[4-(piperidin-1-yl)phen­yl]prop-2-en-1-one

Jasinski, J.P.; Guild, C.J.; Narayana, B.; Nayak, P.S.; Yathirajan, H.S.

doi:10.1107/S1600536810026218

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1996

https://doi.org/10.1107/S1600536810026218

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(E)-3-(4-Methoxyphenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one

Jerry P. Jasinski,^a ^* Curtis J. Guild,^a B. Narayana,^b Prakash S. Nayak ^b and H. S. Yathirajan ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 10 June 2010; accepted 3 July 2010; online 14 July 2010)

The piperidine ring in the title compound, C₂₁H₂₃NO₂, is in a slightly distorted chair conformation. The dihedral angle between the two benzene rings is 5.6 (4)°. The dihedral angles between the propenone unit and the benzene and methoxy-substituted benzene rings are 5.6 (7) and 10.7 (8)°, respectively. Weak intermolecular C—H⋯O hydrogen bonds and weak C—H⋯π interactions contribute to the stability of the crystal structure.

Related literature

For the synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents, see: Bandgar et al. (2010 ). For anti-inflammatory chalcones, see: Nowakowska (2007 ). For related structures, see: Ahmad et al.(2010 ); Arai et al.(1994 ); Jasinski et al. (2010 ); Li et al. (1992 ); Patil et al. (2007 ); Shettigar et al. (2006 ). For standard bond lengths, see; Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₃NO₂
M_r = 321.40
Triclinic, $[P \overline 1]$
a = 6.0963 (11) Å
b = 10.985 (2) Å
c = 13.133 (3) Å
α = 74.188 (3)°
β = 88.674 (3)°
γ = 77.393 (3)°
V = 825.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.36 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.962, T_max = 0.983
10674 measured reflections
4861 independent reflections
3562 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.151
S = 1.05
4861 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.93	2.47	3.2105 (16)	137
C8—H8A⋯Cg3ⁱⁱ	0.97	2.66	3.623 (2)	171
C21—H21A⋯Cg2ⁱⁱⁱ	0.96	2.90	3.823 (2)	162
Symmetry codes: (i) -x+2, -y+2, -z; (ii) x, y, z+1; (iii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026218/lh5070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026218/lh5070Isup2.hkl

checkCIF report

Comment top

The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. A review of anti- infective and anti-inflammatory chalcones is published (Nowakowska, 2007). The synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents is recently reported (Bandgar et al., 2010). The crystal structures of some related chalcones containing methoxy substituents, viz., 4-bromo-4'-methoxy-chalcone (Li et al., 1992), 4-bromo-4'-methoxychalcone (Arai et al., 1994), 1-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Shettigar et al., 2006) and 1-(4-bromophenyl)-3-(3-methoxyphenyl) prop-2-en-1-one (Patil et al., 2007), a monoclinic polymorph of 1-(4-chlorophenyl)-3- (4-methoxyphenyl)prop-2-en-1-one (Jasinski et al., 2010) and (E)-3-(3-chlorophenyl)-1-(4-methoxyphenyl) prop-2-en-1-one (Ahmad et al., 2010) have been reported. Hence in continuation with the synthesis and crystal structure of chalcones and their derivatives, this new chalcone containing the piperidine moiety was synthesized and its crystal structure is reported herein.

The title compound contains phenyl-4-methoxy and phenyl-4-piperidine groups on opposite sides of a 2-propen-1-one moiety (Fig. 1). Bond distances (Allen et al., 1987) and angles are in normal ranges. The piperidine ring is in a slightly distorted chair conformation. The dihedral angles between the two benzene rings is 5.6 (4)°. The dihedral angles between the propenone moiety and the benzene and methoxy-benzene rings are 5.6 (7)° and 10.7 (8)°. A weak intermolecular hydrogen bond and weak intermolecular C—H···π-ring interactions contribute to the stability of crystal packing (Fig. 2).

Related literature top

For the synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents, see: Bandgar et al. (2010). For anti-inflammatory chalcones, see: Nowakowska (2007). For related structures, see: Ahmad et al.(2010); Arai et al.(1994); Jasinski et al. (2010); Li et al. (1992); Patil et al. (2007); Shettigar et al. (2006). For standard bond lengths, see; Allen et al. (1987).

Experimental top

A 30% KOH solution was added to a mixture of 1-[4-(piperidin-1-yl)phenyl] ethanone (0.01 mol, 2.03 g) and 4-methoxy benzaldehyde (0.01 mol, 1.36 g) in 50 ml of ethanol (Fig. 3). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from 1:1 mixture of acetone and toluene by slow evaporation method and yield of the compound was 68% (m.p.391–394 K). Analytical data: Found (Calculated): C %: 78.41 (78.47); H%: 7.18 (7.21); N%: 4.33 (4.36).

Structure description top

For the synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents, see: Bandgar et al. (2010). For anti-inflammatory chalcones, see: Nowakowska (2007). For related structures, see: Ahmad et al.(2010); Arai et al.(1994); Jasinski et al. (2010); Li et al. (1992); Patil et al. (2007); Shettigar et al. (2006). For standard bond lengths, see; Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing of the title compound viewed along the a axis.
	Fig. 3. Reaction Scheme of C₂₁H₂₃N₁O₂,.

(E)-3-(4-Methoxyphenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one top

Crystal data top

C₂₁H₂₃NO₂	Z = 2
M_r = 321.40	F(000) = 344
Triclinic, P1	D_x = 1.294 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0963 (11) Å	Cell parameters from 1958 reflections
b = 10.985 (2) Å	θ = 2.2–30.9°
c = 13.133 (3) Å	µ = 0.08 mm⁻¹
α = 74.188 (3)°	T = 100 K
β = 88.674 (3)°	Block, red
γ = 77.393 (3)°	0.47 × 0.36 × 0.21 mm
V = 825.2 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	4861 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 31.3°, θ_min = 1.6°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −8→8
T_min = 0.962, T_max = 0.983	k = −15→15
10674 measured reflections	l = −18→18

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0703P)² + 0.1716P] where P = (F_o² + 2F_c²)/3
4861 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₂₃NO₂	γ = 77.393 (3)°
M_r = 321.40	V = 825.2 (3) Å³
Triclinic, P1	Z = 2
a = 6.0963 (11) Å	Mo Kα radiation
b = 10.985 (2) Å	µ = 0.08 mm⁻¹
c = 13.133 (3) Å	T = 100 K
α = 74.188 (3)°	0.47 × 0.36 × 0.21 mm
β = 88.674 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4861 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2008)	3562 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.983	R_int = 0.027
10674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
4861 reflections	Δρ_min = −0.25 e Å⁻³
218 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
O1	0.23178 (16)	0.88147 (10)	−0.30730 (7)	0.0256 (2)
O2	1.10171 (16)	0.82032 (10)	0.20063 (7)	0.0233 (2)
N1	0.76112 (17)	0.61303 (11)	0.66686 (8)	0.0172 (2)
C1	0.8660 (2)	0.75063 (12)	0.33849 (9)	0.0166 (2)
C2	1.0241 (2)	0.74601 (13)	0.41547 (10)	0.0197 (3)
H2	1.1548	0.7748	0.3940	0.024*
C3	0.9928 (2)	0.70016 (13)	0.52239 (10)	0.0201 (3)
H3	1.1021	0.6994	0.5710	0.024*
C4	0.7989 (2)	0.65444 (12)	0.55956 (9)	0.0168 (2)
C5	0.6400 (2)	0.65849 (13)	0.48138 (10)	0.0208 (3)
H5	0.5103	0.6282	0.5022	0.025*
C6	0.6729 (2)	0.70647 (13)	0.37468 (10)	0.0199 (3)
H6	0.5630	0.7094	0.3256	0.024*
C7	0.9508 (2)	0.59163 (14)	0.74157 (10)	0.0202 (3)
H7A	1.0243	0.6641	0.7201	0.024*
H7B	1.0594	0.5139	0.7385	0.024*
C8	0.8785 (2)	0.57739 (14)	0.85498 (10)	0.0210 (3)
H8A	0.7896	0.6599	0.8606	0.025*
H8B	1.0111	0.5548	0.9015	0.025*
C9	0.7413 (2)	0.47408 (13)	0.89082 (10)	0.0204 (3)
H9A	0.8332	0.3896	0.8921	0.025*
H9B	0.6895	0.4714	0.9616	0.025*
C10	0.5413 (2)	0.50756 (13)	0.81348 (9)	0.0194 (3)
H10A	0.4555	0.4405	0.8336	0.023*
H10B	0.4440	0.5888	0.8171	0.023*
C11	0.6156 (2)	0.51976 (13)	0.70057 (10)	0.0187 (3)
H11B	0.6961	0.4354	0.6951	0.022*
H11A	0.4836	0.5471	0.6532	0.022*
C12	0.9153 (2)	0.79733 (12)	0.22544 (9)	0.0174 (2)
C13	0.7416 (2)	0.81181 (12)	0.14373 (10)	0.0182 (3)
H13	0.6061	0.7885	0.1641	0.022*
C14	0.7769 (2)	0.85811 (12)	0.04061 (10)	0.0179 (3)
H14	0.9108	0.8853	0.0243	0.021*
C15	0.6283 (2)	0.87041 (12)	−0.04869 (9)	0.0174 (2)
C16	0.4309 (2)	0.82206 (13)	−0.03711 (10)	0.0195 (3)
H16	0.3856	0.7857	0.0304	0.023*
C17	0.3037 (2)	0.82786 (13)	−0.12444 (10)	0.0202 (3)
H17	0.1744	0.7948	−0.1154	0.024*
C18	0.3679 (2)	0.88308 (13)	−0.22624 (10)	0.0198 (3)
C19	0.5590 (2)	0.93488 (13)	−0.23992 (10)	0.0210 (3)
H19	0.6008	0.9739	−0.3074	0.025*
C20	0.6865 (2)	0.92747 (12)	−0.15117 (10)	0.0190 (3)
H20	0.8146	0.9616	−0.1604	0.023*
C21	0.3004 (3)	0.93119 (15)	−0.41233 (10)	0.0265 (3)
H21A	0.3054	1.0207	−0.4238	0.040*
H21B	0.1949	0.9240	−0.4624	0.040*
H21C	0.4470	0.8823	−0.4214	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0261 (5)	0.0332 (6)	0.0188 (5)	−0.0104 (4)	−0.0024 (4)	−0.0061 (4)
O2	0.0210 (5)	0.0296 (5)	0.0216 (5)	−0.0118 (4)	0.0029 (4)	−0.0060 (4)
N1	0.0154 (5)	0.0228 (6)	0.0143 (5)	−0.0079 (4)	−0.0008 (4)	−0.0038 (4)
C1	0.0178 (6)	0.0159 (6)	0.0169 (6)	−0.0039 (4)	0.0006 (4)	−0.0054 (4)
C2	0.0153 (6)	0.0257 (7)	0.0190 (6)	−0.0080 (5)	0.0009 (4)	−0.0047 (5)
C3	0.0164 (6)	0.0268 (7)	0.0173 (6)	−0.0080 (5)	−0.0019 (5)	−0.0036 (5)
C4	0.0157 (6)	0.0182 (6)	0.0166 (6)	−0.0035 (4)	−0.0005 (4)	−0.0050 (5)
C5	0.0161 (6)	0.0295 (7)	0.0192 (6)	−0.0103 (5)	0.0014 (5)	−0.0065 (5)
C6	0.0186 (6)	0.0262 (7)	0.0168 (6)	−0.0085 (5)	−0.0009 (5)	−0.0064 (5)
C7	0.0172 (6)	0.0281 (7)	0.0171 (6)	−0.0097 (5)	−0.0012 (4)	−0.0054 (5)
C8	0.0211 (6)	0.0274 (7)	0.0167 (6)	−0.0094 (5)	−0.0003 (5)	−0.0066 (5)
C9	0.0206 (6)	0.0244 (7)	0.0154 (6)	−0.0059 (5)	0.0011 (5)	−0.0032 (5)
C10	0.0167 (6)	0.0240 (6)	0.0174 (6)	−0.0068 (5)	0.0010 (4)	−0.0034 (5)
C11	0.0166 (6)	0.0222 (6)	0.0183 (6)	−0.0072 (5)	−0.0004 (5)	−0.0048 (5)
C12	0.0201 (6)	0.0161 (6)	0.0163 (6)	−0.0044 (5)	0.0000 (5)	−0.0047 (5)
C13	0.0180 (6)	0.0190 (6)	0.0183 (6)	−0.0054 (5)	0.0003 (5)	−0.0052 (5)
C14	0.0177 (6)	0.0179 (6)	0.0185 (6)	−0.0039 (5)	0.0002 (5)	−0.0057 (5)
C15	0.0187 (6)	0.0154 (6)	0.0182 (6)	−0.0036 (4)	0.0007 (4)	−0.0048 (5)
C16	0.0201 (6)	0.0204 (6)	0.0177 (6)	−0.0057 (5)	0.0031 (5)	−0.0039 (5)
C17	0.0175 (6)	0.0213 (6)	0.0224 (6)	−0.0058 (5)	0.0015 (5)	−0.0057 (5)
C18	0.0201 (6)	0.0210 (6)	0.0182 (6)	−0.0031 (5)	−0.0016 (5)	−0.0062 (5)
C19	0.0226 (6)	0.0219 (6)	0.0177 (6)	−0.0064 (5)	0.0012 (5)	−0.0029 (5)
C20	0.0188 (6)	0.0181 (6)	0.0197 (6)	−0.0052 (5)	0.0020 (5)	−0.0038 (5)
C21	0.0305 (8)	0.0312 (8)	0.0177 (6)	−0.0068 (6)	−0.0013 (5)	−0.0063 (5)

Geometric parameters (Å, º) top

O1—C18	1.3711 (15)	C9—H9B	0.9700
O1—C21	1.4277 (16)	C10—C11	1.5194 (17)
O2—C12	1.2346 (15)	C10—H10A	0.9700
N1—C4	1.3882 (16)	C10—H10B	0.9700
N1—C7	1.4706 (15)	C11—H11B	0.9700
N1—C11	1.4713 (16)	C11—H11A	0.9700
C1—C6	1.3942 (17)	C12—C13	1.4779 (17)
C1—C2	1.3963 (16)	C13—C14	1.3408 (17)
C1—C12	1.4797 (17)	C13—H13	0.9300
C2—C3	1.3806 (17)	C14—C15	1.4575 (17)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.4097 (17)	C15—C20	1.3948 (17)
C3—H3	0.9300	C15—C16	1.4071 (17)
C4—C5	1.4130 (16)	C16—C17	1.3785 (17)
C5—C6	1.3830 (17)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.3949 (18)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.5197 (17)	C18—C19	1.3920 (18)
C7—H7A	0.9700	C19—C20	1.3897 (17)
C7—H7B	0.9700	C19—H19	0.9300
C8—C9	1.5212 (18)	C20—H20	0.9300
C8—H8A	0.9700	C21—H21A	0.9600
C8—H8B	0.9700	C21—H21B	0.9600
C9—C10	1.5207 (17)	C21—H21C	0.9600
C9—H9A	0.9700

C18—O1—C21	116.56 (10)	C11—C10—H10B	109.3
C4—N1—C7	117.45 (10)	C9—C10—H10B	109.3
C4—N1—C11	117.85 (10)	H10A—C10—H10B	108.0
C7—N1—C11	113.84 (10)	N1—C11—C10	112.56 (10)
C6—C1—C2	116.73 (11)	N1—C11—H11B	109.1
C6—C1—C12	124.41 (11)	C10—C11—H11B	109.1
C2—C1—C12	118.84 (11)	N1—C11—H11A	109.1
C3—C2—C1	122.16 (11)	C10—C11—H11A	109.1
C3—C2—H2	118.9	H11B—C11—H11A	107.8
C1—C2—H2	118.9	O2—C12—C13	121.02 (11)
C2—C3—C4	121.43 (11)	O2—C12—C1	119.88 (11)
C2—C3—H3	119.3	C13—C12—C1	119.07 (11)
C4—C3—H3	119.3	C14—C13—C12	120.87 (12)
N1—C4—C3	121.98 (11)	C14—C13—H13	119.6
N1—C4—C5	121.74 (11)	C12—C13—H13	119.6
C3—C4—C5	116.22 (11)	C13—C14—C15	127.06 (12)
C6—C5—C4	121.47 (12)	C13—C14—H14	116.5
C6—C5—H5	119.3	C15—C14—H14	116.5
C4—C5—H5	119.3	C20—C15—C16	117.66 (11)
C5—C6—C1	121.97 (11)	C20—C15—C14	119.35 (11)
C5—C6—H6	119.0	C16—C15—C14	122.93 (11)
C1—C6—H6	119.0	C17—C16—C15	120.88 (12)
N1—C7—C8	112.76 (10)	C17—C16—H16	119.6
N1—C7—H7A	109.0	C15—C16—H16	119.6
C8—C7—H7A	109.0	C16—C17—C18	120.37 (12)
N1—C7—H7B	109.0	C16—C17—H17	119.8
C8—C7—H7B	109.0	C18—C17—H17	119.8
H7A—C7—H7B	107.8	O1—C18—C19	124.56 (12)
C7—C8—C9	112.12 (10)	O1—C18—C17	115.48 (11)
C7—C8—H8A	109.2	C19—C18—C17	119.96 (11)
C9—C8—H8A	109.2	C20—C19—C18	119.01 (12)
C7—C8—H8B	109.2	C20—C19—H19	120.5
C9—C8—H8B	109.2	C18—C19—H19	120.5
H8A—C8—H8B	107.9	C19—C20—C15	122.08 (12)
C10—C9—C8	108.32 (10)	C19—C20—H20	119.0
C10—C9—H9A	110.0	C15—C20—H20	119.0
C8—C9—H9A	110.0	O1—C21—H21A	109.5
C10—C9—H9B	110.0	O1—C21—H21B	109.5
C8—C9—H9B	110.0	H21A—C21—H21B	109.5
H9A—C9—H9B	108.4	O1—C21—H21C	109.5
C11—C10—C9	111.56 (10)	H21A—C21—H21C	109.5
C11—C10—H10A	109.3	H21B—C21—H21C	109.5
C9—C10—H10A	109.3

C6—C1—C2—C3	0.01 (19)	C6—C1—C12—O2	−171.55 (13)
C12—C1—C2—C3	−178.13 (12)	C2—C1—C12—O2	6.44 (18)
C1—C2—C3—C4	0.5 (2)	C6—C1—C12—C13	6.57 (19)
C7—N1—C4—C3	−12.83 (18)	C2—C1—C12—C13	−175.44 (11)
C11—N1—C4—C3	−154.97 (12)	O2—C12—C13—C14	−4.24 (19)
C7—N1—C4—C5	170.04 (11)	C1—C12—C13—C14	177.66 (11)
C11—N1—C4—C5	27.90 (18)	C12—C13—C14—C15	176.00 (11)
C2—C3—C4—N1	−177.33 (12)	C13—C14—C15—C20	176.56 (12)
C2—C3—C4—C5	−0.05 (19)	C13—C14—C15—C16	−6.3 (2)
N1—C4—C5—C6	176.42 (12)	C20—C15—C16—C17	1.80 (19)
C3—C4—C5—C6	−0.9 (2)	C14—C15—C16—C17	−175.43 (12)
C4—C5—C6—C1	1.4 (2)	C15—C16—C17—C18	−0.6 (2)
C2—C1—C6—C5	−0.95 (19)	C21—O1—C18—C19	3.18 (19)
C12—C1—C6—C5	177.09 (12)	C21—O1—C18—C17	−176.80 (11)
C4—N1—C7—C8	166.66 (11)	C16—C17—C18—O1	178.77 (11)
C11—N1—C7—C8	−49.73 (15)	C16—C17—C18—C19	−1.2 (2)
N1—C7—C8—C9	53.10 (15)	O1—C18—C19—C20	−178.31 (12)
C7—C8—C9—C10	−55.90 (15)	C17—C18—C19—C20	1.7 (2)
C8—C9—C10—C11	56.61 (14)	C18—C19—C20—C15	−0.4 (2)
C4—N1—C11—C10	−165.90 (11)	C16—C15—C20—C19	−1.33 (19)
C7—N1—C11—C10	50.64 (15)	C14—C15—C20—C19	176.00 (12)
C9—C10—C11—N1	−54.75 (15)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.93	2.47	3.2105 (16)	137
C8—H8A···Cg3ⁱⁱ	0.97	2.66	3.623 (2)	171
C21—H21A···Cg2ⁱⁱⁱ	0.96	2.90	3.823 (2)	162

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₂
M_r	321.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.0963 (11), 10.985 (2), 13.133 (3)
α, β, γ (°)	74.188 (3), 88.674 (3), 77.393 (3)
V (Å³)	825.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.36 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (APEX2; Bruker, 2008)
T_min, T_max	0.962, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10674, 4861, 3562
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.730

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.151, 1.05
No. of reflections	4861
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.93	2.47	3.2105 (16)	136.5
C8—H8A···Cg3ⁱⁱ	0.97	2.66	3.623 (2)	171
C21—H21A···Cg2ⁱⁱⁱ	0.96	2.90	3.823 (2)	162

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

Acknowledgements

BN thanks the UGC (New Delhi) for the SAP chemical grant. HSY thanks UOM for sabbatical leave. JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by the Ohio Board of Regents grant CAP-491, and by YSU.

References

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