Ethyl 3-methyl-2,6-diphenyl­piperidine-1-carboxyl­ate

Natarajan, S.; Mathews, R.

doi:10.1107/S1600536811019155

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1530

doi:10.1107/S1600536811019155

Open

access

Ethyl 3-methyl-2,6-diphenylpiperidine-1-carboxylate

Sampath Natarajan ^a ^* and Rita Mathews ^a

^aDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul-143 701, Republic of Korea
^*Correspondence e-mail: sampath@konkuk.ac.kr

(Received 18 April 2011; accepted 19 May 2011; online 25 May 2011)

In the title compound, C₂₁H₂₅NO₂, the piperidine ring adopts a twisted boat conformation characterized by puckering parameters θ = 89.5 (1) and φ = 257.5 (2)°. The phenyl groups are located in equatorial and axial positions on the central piperidine ring, while the methyl group is in an equatorial position. The dihedral angle between the phenyl rings is 49.8 (1)°. An intramolecular C—H⋯O interaction occurs. The crystal structure features weak intermolecular C—H⋯O interactions and a stabilizing intermolecular C—H⋯π contact involving the axial phenyl ring.

Related literature

For the biological activity of related piperidines, see: Parthiban et al. (2009 ); Aridoss et al. (2007 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1995 ). For the conformation of piperidine derivatives, see: Ravindran et al. (1991 ); Krishna Kumar & Krishna Pillay (1996 ). For the synthesis of the title compound, see: Sampath et al. (2003 ); Noller & Baliah (1948 ).

Experimental

Crystal data

C₂₁H₂₅NO₂
M_r = 323.42
Monoclinic, P 2₁ /n
a = 10.4113 (3) Å
b = 10.6073 (6) Å
c = 16.2782 (6) Å
β = 95.960 (2)°
V = 1787.98 (13) Å³
Z = 4
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.26 × 0.22 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3698 measured reflections
3502 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.012
Standard reflections: 3; every 60 minutes intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.136
S = 1.03
3502 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1	0.93	2.91	3.519 (2)	125
C14—H14⋯O2ⁱ	0.93	2.82	3.406 (2)	122
C10—H10⋯O1ⁱⁱ	0.93	2.67	3.460 (3)	144
C3—H3B⋯Cg1ⁱⁱⁱ	0.97	2.70	3.666 (2)	172
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019155/bh2353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019155/bh2353Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019155/bh2353Isup3.cml

checkCIF report

Comment top

Piperidines and its N-substituted derivatives show significant pharmacological properties (Parthiban et al., 2009; Aridoss et al., 2007). Substitution by electron withdrawing groups (CHO, COCH₂CH₃, COPh, NO, etc.) at N-th position of piperidine ring causes major changes in the ring conformation (Ravindran et al., 1991; Krishna Kumar & Krishna Pillay, 1996). In the title compound (Fig. 1), the ethylacetate group substituting the piperidine ring shows extended conformation and the hetero π electron delocalization through the atoms N1, C20, O1 and O2 causes twisted boat conformation for the piperidine core, with puckering amplitude, Q_T = 0.718 (1) Å and phase angle = 89.5 (2)° (Nardelli, 1995; Cremer & Pople, 1975).

The phenyl rings at C2 and C6 atoms are oriented in the axial and equatorial positions, respectively, and the dihedral angle between them is 49.8 (1)°. Similarly, the methyl group at C5 is also oriented in equatorial position. All these substitutions are confirmed by the respective torsion angles. In addition, the substitution of ethylacetate group on N1 atom showed extended conformation with respect to the piperidine ring, which is also confirmed by the torsion angles.

The packing diagram of the title compound viewed down a-axis is shown in Fig. 2. The molecules did not present any classical H-bonds. However, the molecules are involved in weak intra- and intermolecular C—H···O interactions (Table 1), which stabilize the molecules in the crystal packing. Interestingly, a C—H···π interaction (C3—H3B···Cg1; Cg1 is the centroid of the ring C13···C18) also helps for the crystal packing.

Related literature top

For the biological activity of related piperidines, see: Parthiban et al. (2009); Aridoss et al. (2007). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1995). For the conformation of piperidine derivatives, see: Ravindran et al. (1991); Krishna Kumar & Krishna Pillay (1996). For the synthesis of the title compound, see: Sampath et al. (2003); Noller & Baliah (1948).

Experimental top

The compound, 3-methyl-2,6-diphenylpiperidin-4-one was obtained by adopting an earlier method (Sampath et al., 2003; Noller & Baliah, 1948) and it was reduced using amalgamated zinc in aqueous methanol solution in the presence of HCl, giving 3-methyl-2,6-diphenylpiperidine as a product. To a well stirred solution of 3,5-dimethyl-2,6-diphenylpiperidin-4-one (2 mM) and triethylamine (4 mM) in freshly distilled benzene (50 ml), a little excess amount of ethylchloroacetate (2.2 mM) in benzene (10 ml) was added drop-wise over about half an hour and stirring was continued until the completion of reaction. The reaction mixture was then poured into water and extracted with dichloromethane. Recrystallization of the title compound using pure ethanol resulted in suitable colorless crystals.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP diagram of the title molecule with displacement ellipsoid drawn at the 30% probability level. Hydrogen atoms were removed for clarity.
	Fig. 2. A unit cell packing of the crystal structure of the title compound viewed down a-axis.

Ethyl 3-methyl-2,6-diphenylpiperidine-1-carboxylate top

Crystal data top

C₂₁H₂₅NO₂	F(000) = 696
M_r = 323.42	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.4113 (3) Å	θ = 0–90°
b = 10.6073 (6) Å	µ = 0.60 mm⁻¹
c = 16.2782 (6) Å	T = 293 K
β = 95.960 (2)°	Needle, colourless
V = 1787.98 (13) Å³	0.26 × 0.22 × 0.18 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.012
Radiation source: fine-focus sealed tube	θ_max = 72.0°, θ_min = 4.8°
Graphite monochromator	h = 0→12
ω scans	k = 0→13
3698 measured reflections	l = −20→19
3502 independent reflections	3 standard reflections every 60 min
2428 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0736P)² + 0.2748P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3502 reflections	Δρ_max = 0.17 e Å⁻³
218 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0022 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₂₅NO₂	V = 1787.98 (13) Å³
M_r = 323.42	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.4113 (3) Å	µ = 0.60 mm⁻¹
b = 10.6073 (6) Å	T = 293 K
c = 16.2782 (6) Å	0.26 × 0.22 × 0.18 mm
β = 95.960 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.012
3698 measured reflections	3 standard reflections every 60 min
3502 independent reflections	intensity decay: none
2428 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
3502 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.92030 (13)	0.42372 (12)	0.12110 (7)	0.0586 (4)
O2	0.99447 (12)	0.61660 (11)	0.15872 (7)	0.0516 (3)
N1	0.90776 (13)	0.49725 (13)	0.25183 (8)	0.0427 (3)
C2	0.81474 (15)	0.39802 (16)	0.26812 (10)	0.0455 (4)
H2	0.7841	0.3620	0.2142	0.055*
C3	0.69751 (17)	0.45929 (18)	0.30030 (11)	0.0516 (4)
H3A	0.6370	0.3939	0.3123	0.062*
H3B	0.6550	0.5127	0.2574	0.062*
C4	0.73118 (18)	0.5382 (2)	0.37787 (12)	0.0584 (5)
H4A	0.7073	0.4918	0.4254	0.070*
H4B	0.6810	0.6153	0.3735	0.070*
C5	0.87457 (16)	0.57150 (17)	0.39184 (10)	0.0470 (4)
H5	0.9212	0.4975	0.4155	0.056*
C6	0.92925 (15)	0.60452 (16)	0.30998 (9)	0.0414 (4)
H6	0.8820	0.6777	0.2857	0.050*
C7	1.07053 (16)	0.63999 (16)	0.32679 (9)	0.0435 (4)
C8	1.16351 (18)	0.55226 (19)	0.35314 (13)	0.0587 (5)
H8	1.1416	0.4675	0.3555	0.070*
C9	1.2899 (2)	0.5901 (2)	0.37612 (15)	0.0718 (6)
H9	1.3516	0.5301	0.3942	0.086*
C10	1.3249 (2)	0.7134 (2)	0.37269 (14)	0.0680 (6)
H10	1.4095	0.7378	0.3888	0.082*
C11	1.2344 (2)	0.8007 (2)	0.34532 (14)	0.0686 (6)
H11	1.2576	0.8851	0.3421	0.082*
C12	1.10831 (19)	0.76434 (18)	0.32231 (12)	0.0563 (5)
H12	1.0477	0.8249	0.3034	0.068*
C13	0.87742 (17)	0.28998 (16)	0.31910 (10)	0.0459 (4)
C14	0.81423 (19)	0.22492 (19)	0.37698 (11)	0.0565 (5)
H14	0.7339	0.2528	0.3897	0.068*
C15	0.8691 (2)	0.1193 (2)	0.41592 (12)	0.0676 (6)
H15	0.8256	0.0768	0.4546	0.081*
C16	0.9876 (2)	0.0766 (2)	0.39778 (13)	0.0685 (6)
H16	1.0241	0.0051	0.4237	0.082*
C17	1.0513 (2)	0.1403 (2)	0.34120 (13)	0.0657 (5)
H17	1.1318	0.1121	0.3291	0.079*
C18	0.99719 (19)	0.24578 (18)	0.30200 (12)	0.0558 (5)
H18	1.0416	0.2879	0.2636	0.067*
C19	0.8953 (2)	0.6789 (2)	0.45370 (11)	0.0642 (5)
H19A	0.9856	0.6992	0.4622	0.096*
H19B	0.8659	0.6536	0.5052	0.096*
H19C	0.8476	0.7515	0.4328	0.096*
C20	0.93902 (16)	0.50599 (16)	0.17288 (10)	0.0440 (4)
C21	1.0362 (2)	0.6314 (2)	0.07700 (12)	0.0637 (5)
H21A	0.9644	0.6169	0.0351	0.076*
H21B	1.1039	0.5713	0.0688	0.076*
C22	1.0848 (3)	0.7612 (2)	0.07088 (15)	0.0802 (7)
H22A	1.1132	0.7740	0.0172	0.120*
H22B	1.1558	0.7744	0.1125	0.120*
H22C	1.0169	0.8199	0.0789	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0793 (9)	0.0536 (8)	0.0446 (7)	−0.0032 (7)	0.0148 (6)	−0.0103 (6)
O2	0.0663 (8)	0.0519 (7)	0.0388 (6)	−0.0084 (6)	0.0165 (5)	0.0009 (5)
N1	0.0506 (8)	0.0425 (7)	0.0355 (7)	−0.0050 (6)	0.0076 (6)	−0.0007 (6)
C2	0.0476 (9)	0.0477 (9)	0.0408 (8)	−0.0065 (7)	0.0024 (7)	0.0012 (7)
C3	0.0453 (9)	0.0592 (11)	0.0500 (10)	−0.0015 (8)	0.0038 (7)	0.0055 (8)
C4	0.0522 (10)	0.0690 (13)	0.0566 (11)	−0.0021 (9)	0.0179 (8)	−0.0046 (9)
C5	0.0513 (9)	0.0530 (10)	0.0378 (8)	−0.0001 (8)	0.0095 (7)	−0.0017 (7)
C6	0.0464 (9)	0.0409 (8)	0.0376 (8)	0.0002 (7)	0.0068 (6)	−0.0019 (6)
C7	0.0476 (9)	0.0451 (9)	0.0386 (8)	−0.0019 (7)	0.0077 (7)	−0.0015 (7)
C8	0.0526 (11)	0.0519 (11)	0.0712 (12)	−0.0010 (9)	0.0048 (9)	0.0060 (9)
C9	0.0508 (11)	0.0749 (15)	0.0881 (16)	0.0031 (10)	0.0001 (10)	0.0103 (12)
C10	0.0519 (11)	0.0813 (15)	0.0705 (13)	−0.0152 (11)	0.0052 (9)	−0.0012 (11)
C11	0.0689 (13)	0.0583 (12)	0.0788 (14)	−0.0205 (11)	0.0080 (11)	−0.0033 (11)
C12	0.0594 (11)	0.0460 (10)	0.0630 (11)	−0.0039 (9)	0.0044 (9)	−0.0018 (8)
C13	0.0528 (9)	0.0429 (9)	0.0414 (8)	−0.0076 (7)	0.0023 (7)	−0.0010 (7)
C14	0.0594 (11)	0.0592 (11)	0.0507 (10)	−0.0094 (9)	0.0047 (8)	0.0073 (9)
C15	0.0900 (16)	0.0600 (12)	0.0514 (11)	−0.0104 (11)	0.0015 (10)	0.0136 (9)
C16	0.0953 (16)	0.0522 (12)	0.0539 (11)	0.0051 (11)	−0.0124 (11)	0.0025 (9)
C17	0.0695 (13)	0.0556 (12)	0.0705 (13)	0.0114 (10)	0.0005 (10)	−0.0046 (10)
C18	0.0613 (11)	0.0481 (10)	0.0591 (10)	0.0012 (9)	0.0116 (9)	−0.0002 (8)
C19	0.0748 (13)	0.0732 (14)	0.0466 (10)	−0.0042 (11)	0.0162 (9)	−0.0146 (9)
C20	0.0492 (9)	0.0448 (9)	0.0389 (8)	0.0021 (7)	0.0094 (7)	0.0016 (7)
C21	0.0800 (13)	0.0707 (13)	0.0445 (10)	−0.0055 (11)	0.0266 (9)	0.0037 (9)
C22	0.0898 (16)	0.0844 (16)	0.0706 (13)	−0.0249 (13)	0.0288 (12)	0.0115 (12)

Geometric parameters (Å, º) top

O1—C20	1.2148 (19)	C10—C11	1.362 (3)
O2—C20	1.338 (2)	C10—H10	0.9300
O2—C21	1.4500 (19)	C11—C12	1.382 (3)
N1—C20	1.3612 (19)	C11—H11	0.9300
N1—C2	1.473 (2)	C12—H12	0.9300
N1—C6	1.482 (2)	C13—C18	1.387 (2)
C2—C13	1.522 (2)	C13—C14	1.388 (2)
C2—C3	1.523 (2)	C14—C15	1.382 (3)
C2—H2	0.9800	C14—H14	0.9300
C3—C4	1.525 (3)	C15—C16	1.375 (3)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.368 (3)
C4—C5	1.528 (2)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.379 (3)
C4—H4B	0.9700	C17—H17	0.9300
C5—C19	1.521 (2)	C18—H18	0.9300
C5—C6	1.543 (2)	C19—H19A	0.9600
C5—H5	0.9800	C19—H19B	0.9600
C6—C7	1.515 (2)	C19—H19C	0.9600
C6—H6	0.9800	C21—C22	1.474 (3)
C7—C8	1.379 (2)	C21—H21A	0.9700
C7—C12	1.381 (2)	C21—H21B	0.9700
C8—C9	1.389 (3)	C22—H22A	0.9600
C8—H8	0.9300	C22—H22B	0.9600
C9—C10	1.361 (3)	C22—H22C	0.9600
C9—H9	0.9300

C20—O2—C21	115.37 (14)	C10—C11—C12	120.3 (2)
C20—N1—C2	116.41 (13)	C10—C11—H11	119.9
C20—N1—C6	121.04 (13)	C12—C11—H11	119.9
C2—N1—C6	119.48 (12)	C7—C12—C11	121.33 (19)
N1—C2—C13	112.56 (13)	C7—C12—H12	119.3
N1—C2—C3	108.81 (14)	C11—C12—H12	119.3
C13—C2—C3	116.58 (14)	C18—C13—C14	117.88 (17)
N1—C2—H2	106.0	C18—C13—C2	119.25 (15)
C13—C2—H2	106.0	C14—C13—C2	122.56 (16)
C3—C2—H2	106.0	C15—C14—C13	120.83 (19)
C2—C3—C4	113.29 (15)	C15—C14—H14	119.6
C2—C3—H3A	108.9	C13—C14—H14	119.6
C4—C3—H3A	108.9	C16—C15—C14	120.4 (2)
C2—C3—H3B	108.9	C16—C15—H15	119.8
C4—C3—H3B	108.9	C14—C15—H15	119.8
H3A—C3—H3B	107.7	C17—C16—C15	119.4 (2)
C3—C4—C5	112.78 (14)	C17—C16—H16	120.3
C3—C4—H4A	109.0	C15—C16—H16	120.3
C5—C4—H4A	109.0	C16—C17—C18	120.6 (2)
C3—C4—H4B	109.0	C16—C17—H17	119.7
C5—C4—H4B	109.0	C18—C17—H17	119.7
H4A—C4—H4B	107.8	C17—C18—C13	120.92 (19)
C19—C5—C4	109.96 (15)	C17—C18—H18	119.5
C19—C5—C6	111.23 (15)	C13—C18—H18	119.5
C4—C5—C6	111.50 (14)	C5—C19—H19A	109.5
C19—C5—H5	108.0	C5—C19—H19B	109.5
C4—C5—H5	108.0	H19A—C19—H19B	109.5
C6—C5—H5	108.0	C5—C19—H19C	109.5
N1—C6—C7	112.66 (13)	H19A—C19—H19C	109.5
N1—C6—C5	109.43 (13)	H19B—C19—H19C	109.5
C7—C6—C5	109.80 (13)	O1—C20—O2	123.46 (15)
N1—C6—H6	108.3	O1—C20—N1	124.70 (16)
C7—C6—H6	108.3	O2—C20—N1	111.84 (14)
C5—C6—H6	108.3	O2—C21—C22	107.49 (17)
C8—C7—C12	117.81 (17)	O2—C21—H21A	110.2
C8—C7—C6	121.71 (16)	C22—C21—H21A	110.2
C12—C7—C6	120.28 (16)	O2—C21—H21B	110.2
C7—C8—C9	120.24 (19)	C22—C21—H21B	110.2
C7—C8—H8	119.9	H21A—C21—H21B	108.5
C9—C8—H8	119.9	C21—C22—H22A	109.5
C10—C9—C8	121.1 (2)	C21—C22—H22B	109.5
C10—C9—H9	119.4	H22A—C22—H22B	109.5
C8—C9—H9	119.4	C21—C22—H22C	109.5
C9—C10—C11	119.2 (2)	H22A—C22—H22C	109.5
C9—C10—H10	120.4	H22B—C22—H22C	109.5
C11—C10—H10	120.4

C20—N1—C2—C13	108.65 (16)	C8—C9—C10—C11	−0.8 (4)
C6—N1—C2—C13	−90.94 (17)	C9—C10—C11—C12	0.8 (3)
C20—N1—C2—C3	−120.56 (16)	C8—C7—C12—C11	−1.5 (3)
C6—N1—C2—C3	39.84 (19)	C6—C7—C12—C11	173.46 (16)
N1—C2—C3—C4	−57.33 (19)	C10—C11—C12—C7	0.4 (3)
C13—C2—C3—C4	71.2 (2)	N1—C2—C13—C18	−41.5 (2)
C2—C3—C4—C5	17.3 (2)	C3—C2—C13—C18	−168.23 (16)
C3—C4—C5—C19	163.67 (16)	N1—C2—C13—C14	145.07 (16)
C3—C4—C5—C6	39.8 (2)	C3—C2—C13—C14	18.3 (2)
C20—N1—C6—C7	−62.3 (2)	C18—C13—C14—C15	−0.2 (3)
C2—N1—C6—C7	138.25 (14)	C2—C13—C14—C15	173.29 (17)
C20—N1—C6—C5	175.28 (14)	C13—C14—C15—C16	−0.1 (3)
C2—N1—C6—C5	15.8 (2)	C14—C15—C16—C17	0.5 (3)
C19—C5—C6—N1	179.64 (15)	C15—C16—C17—C18	−0.5 (3)
C4—C5—C6—N1	−57.23 (19)	C16—C17—C18—C13	0.2 (3)
C19—C5—C6—C7	55.50 (19)	C14—C13—C18—C17	0.2 (3)
C4—C5—C6—C7	178.64 (15)	C2—C13—C18—C17	−173.55 (17)
N1—C6—C7—C8	−53.5 (2)	C21—O2—C20—O1	−2.2 (3)
C5—C6—C7—C8	68.8 (2)	C21—O2—C20—N1	177.33 (15)
N1—C6—C7—C12	131.73 (16)	C2—N1—C20—O1	−17.4 (2)
C5—C6—C7—C12	−106.04 (18)	C6—N1—C20—O1	−177.46 (16)
C12—C7—C8—C9	1.6 (3)	C2—N1—C20—O2	163.14 (14)
C6—C7—C8—C9	−173.36 (18)	C6—N1—C20—O2	3.1 (2)
C7—C8—C9—C10	−0.4 (3)	C20—O2—C21—C22	175.60 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.98	2.28	2.749 (2)	109
C18—H18···O1	0.93	2.91	3.519 (2)	125
C14—H14···O2ⁱ	0.93	2.82	3.406 (2)	122
C10—H10···O1ⁱⁱ	0.93	2.67	3.460 (3)	144
C3—H3B···Cg1ⁱⁱⁱ	0.97	2.70	3.666 (2)	172

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₂
M_r	323.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.4113 (3), 10.6073 (6), 16.2782 (6)
β (°)	95.960 (2)
V (Å³)	1787.98 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.26 × 0.22 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3698, 3502, 2428
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.136, 1.03
No. of reflections	3502
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms, 1996), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1	0.93	2.91	3.519 (2)	125
C14—H14···O2ⁱ	0.93	2.82	3.406 (2)	122
C10—H10···O1ⁱⁱ	0.93	2.67	3.460 (3)	144
C3—H3B···Cg1ⁱⁱⁱ	0.97	2.70	3.666 (2)	172

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

References

Aridoss, G., Balasubramanian, S., Parthiban, P., Ramachandran, R. & Kabilan, S. (2007). Med. Chem. Res. 16, 188–204. Web of Science CrossRef CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. (1996). XCAD4. University of Marburg, Germany. Google Scholar
Krishna Kumar, R. & Krishna Pillay, M. (1996). Indian J. Chem. Sect. B, 35, 418–425. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Noller, C. R. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853–3855. CrossRef PubMed CAS Web of Science Google Scholar
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 2981–2985. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ravindran, T., Jeyaraman, R., Murray, R. W. & Singh, M. (1991). J. Org. Chem. 56, 4833–4840. CrossRef CAS Web of Science Google Scholar
Sampath, N., Malathy Sony, S. M., Ponnuswamy, M. N. & Nethaji, M. (2003). Acta Cryst. C59, o346–o348. Web of Science CSD CrossRef CAS IUCr Journals 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

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| Page o1530

doi:10.1107/S1600536811019155

Open

access