Ethyl 1-cyclo­hexyl-5-(4-meth­oxy­phen­yl)-1H-pyrazole-4-carboxyl­ate

Fun, H.-K.; Quah, C.K.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536811049282

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3460-o3461

https://doi.org/10.1107/S1600536811049282

Open

access

Ethyl 1-cyclohexyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § B. Chandrakantha,^b A. M. Isloor ^c and Prakash Shetty ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India, ^cMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 November 2011; accepted 18 November 2011; online 30 November 2011)

In the title compound, C₁₉H₂₄N₂O₃, the benzene ring forms a dihedral angle of 65.34 (7)° with the pyrazole ring. The cyclohexane ring adopts a chair conformation. In the crystal, molecules are linked into a inversion dimers by pairs of C—H⋯O hydrogen bonds, generating R₂²(22) ring motifs.

Related literature

For general background to pyrazole derivatives, see: Dhanya et al. (2009 ); Hall et al. (2008 ); Isloor et al. (2000 , 2009 ); Ragavan et al. (2010 ); Premsai Rai et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2010a ,b , 2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₃
M_r = 328.40
Triclinic, $[P \overline 1]$
a = 6.8959 (7) Å
b = 11.0858 (7) Å
c = 12.0142 (12) Å
α = 100.690 (2)°
β = 93.107 (1)°
γ = 95.354 (1)°
V = 896.16 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.31 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.988
18767 measured reflections
5159 independent reflections
3928 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.164
S = 1.05
5159 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.96	2.44	3.358 (2)	159
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536811049282/is5014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049282/is5014Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049282/is5014Isup3.cml

checkCIF report

Comment top

Pyrazoles and their derivatives play an important role in medicinal chemistry (Dhanya et al., 2009). Several derivatives of pyrazole are of pharmaceutical interest due to their analgesic action. Pyrazole molecules also exhibit anticancer (Hall et al., 2008), anti-inflammatory, antidepressant, anticonvulsant and anti-HIV properties (Isloor et al., 2000, 2009). During the past years, considerable evidence has been accumulated to demonstrate the efficacy of pyrazole derivatives. The incorporation of aryl system into the pyrazole ring enhances the biological activities to a great extent (Ragavan et al., 2010). Presence of different substituents, both on the pyrazole ring and on the phenyl ring, can severely modify the biological properties of such molecules (Premsai Rai et al., 2009). Keeping in view of the importance of the pyrazole derivatives, we hereby report the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. The benzene ring (C10–C15) forms a dihedral angle of 65.34 (7)° with the pyrazole ring (N1/N2/C1–C3). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2010a,b, 2011). The cyclohexane ring (C4–C9) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.5694 (17) Å, Θ = 177.82 (16)° and φ = 182 (5)°.

In the crystal (Fig. 2), molecules are linked into an inversion dimer by a pair of intermolecular C16—H16A···O2 hydrogen bonds (Table 1), generating an R²₂(22) ring motif (Bernstein et al., 1995).

Related literature top

For general background to pyrazole derivatives, see: Dhanya et al. (2009); Hall et al. (2008); Isloor et al. (2000, 2009); Ragavan et al. (2010); Premsai Rai et al. (2009). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2010a,b, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of ethyl 4-methoxy benzoyl acetate (2.0 g, 0.0090 mol) and N,N-dimethylformamide dimethyl acetal (20 ml) was heated to reflux for 18 h. The excess of acetal was distilled off under reduced pressure and the residue was purified by column chromatography using 60-120 silica gel mesh size with chloroform and methanol as an eluent to give yellow liquid (2.0 g, 95 %). A mixture of ethyl-3-(dimethylamino)-2-(4-methoxyphenylcarbonyl)prop-2-enoate (2.0 g, 0.0088 mol) and cyclohexyl hydrazine (1.1 g, 0.0096 mol) in absolute ethanol (20 ml) was refluxed for 2 h. On cooling, the separated colorless needle-shaped crystals of title compound were collected by filtration. Compound was recrystallized from ethanol (yield 2.5 g, 89%; m.p. 413-418 K).

Structure description top

For general background to pyrazole derivatives, see: Dhanya et al. (2009); Hall et al. (2008); Isloor et al. (2000, 2009); Ragavan et al. (2010); Premsai Rai et al. (2009). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2010a,b, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Ethyl 1-cyclohexyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate top

Crystal data top

C₁₉H₂₄N₂O₃	Z = 2
M_r = 328.40	F(000) = 352
Triclinic, P1	D_x = 1.217 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8959 (7) Å	Cell parameters from 6690 reflections
b = 11.0858 (7) Å	θ = 2.8–30.0°
c = 12.0142 (12) Å	µ = 0.08 mm⁻¹
α = 100.690 (2)°	T = 296 K
β = 93.107 (1)°	Needle, colourless
γ = 95.354 (1)°	0.40 × 0.31 × 0.15 mm
V = 896.16 (14) Å³

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5159 independent reflections
Radiation source: fine-focus sealed tube	3928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 30.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.968, T_max = 0.988	k = −15→15
18767 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0889P)² + 0.118P] where P = (F_o² + 2F_c²)/3
5159 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₂₄N₂O₃	γ = 95.354 (1)°
M_r = 328.40	V = 896.16 (14) Å³
Triclinic, P1	Z = 2
a = 6.8959 (7) Å	Mo Kα radiation
b = 11.0858 (7) Å	µ = 0.08 mm⁻¹
c = 12.0142 (12) Å	T = 296 K
α = 100.690 (2)°	0.40 × 0.31 × 0.15 mm
β = 93.107 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5159 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3928 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.988	R_int = 0.021
18767 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
5159 reflections	Δρ_min = −0.23 e Å⁻³
219 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.24481 (16)	0.40833 (10)	0.42125 (10)	0.0637 (3)
O2	−0.1292 (2)	0.87054 (11)	0.39497 (11)	0.0756 (4)
O3	−0.17512 (15)	1.04017 (9)	0.32770 (9)	0.0579 (3)
N1	0.20159 (16)	0.93769 (11)	0.08374 (10)	0.0500 (3)
N2	0.24537 (14)	0.83382 (9)	0.12036 (9)	0.0416 (2)
C1	0.15217 (15)	0.81617 (10)	0.21339 (9)	0.0366 (2)
C2	0.04032 (16)	0.91465 (11)	0.23818 (10)	0.0387 (2)
C3	0.07815 (18)	0.98587 (12)	0.15498 (12)	0.0462 (3)
H3A	0.0227	1.0583	0.1507	0.055*
C4	0.37555 (16)	0.75420 (12)	0.05627 (10)	0.0424 (3)
H4A	0.3759	0.6789	0.0880	0.051*
C5	0.3032 (2)	0.71696 (17)	−0.06831 (13)	0.0634 (4)
H5A	0.2978	0.7901	−0.1014	0.076*
H5B	0.1724	0.6744	−0.0750	0.076*
C6	0.4396 (2)	0.63269 (18)	−0.13218 (14)	0.0705 (5)
H6A	0.4338	0.5560	−0.1041	0.085*
H6B	0.3960	0.6133	−0.2122	0.085*
C7	0.6475 (2)	0.69171 (17)	−0.11840 (13)	0.0630 (4)
H7A	0.7311	0.6333	−0.1555	0.076*
H7B	0.6564	0.7628	−0.1550	0.076*
C8	0.7178 (2)	0.73191 (17)	0.00499 (13)	0.0624 (4)
H8A	0.8481	0.7750	0.0109	0.075*
H8B	0.7248	0.6597	0.0393	0.075*
C9	0.58264 (18)	0.81614 (15)	0.06897 (13)	0.0562 (4)
H9A	0.6275	0.8367	0.1488	0.067*
H9B	0.5857	0.8922	0.0398	0.067*
C10	0.17434 (16)	0.70935 (10)	0.26810 (10)	0.0371 (2)
C11	0.35203 (17)	0.69279 (12)	0.32133 (11)	0.0438 (3)
H11A	0.4596	0.7504	0.3226	0.053*
C12	0.37068 (19)	0.59210 (12)	0.37225 (11)	0.0481 (3)
H12A	0.4899	0.5828	0.4080	0.058*
C13	0.21233 (19)	0.50493 (11)	0.37021 (10)	0.0438 (3)
C14	0.03437 (19)	0.52023 (12)	0.31811 (12)	0.0475 (3)
H14A	−0.0729	0.4624	0.3168	0.057*
C15	0.01701 (17)	0.62194 (12)	0.26809 (11)	0.0463 (3)
H15A	−0.1030	0.6318	0.2337	0.056*
C16	0.0922 (3)	0.31069 (15)	0.41146 (16)	0.0671 (4)
H16A	0.1307	0.2515	0.4552	0.101*
H16B	0.0667	0.2713	0.3332	0.101*
H16C	−0.0238	0.3433	0.4394	0.101*
C17	−0.09192 (17)	0.93662 (11)	0.32911 (10)	0.0424 (3)
C18	−0.3166 (3)	1.06986 (18)	0.41045 (15)	0.0714 (5)
H18A	−0.3792	0.9945	0.4285	0.086*
H18B	−0.2514	1.1194	0.4798	0.086*
C19	−0.4606 (3)	1.1369 (3)	0.3653 (2)	0.1087 (9)
H19A	−0.5482	1.1625	0.4225	0.163*
H19B	−0.5330	1.0848	0.3008	0.163*
H19C	−0.3971	1.2082	0.3425	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0735 (7)	0.0545 (6)	0.0701 (7)	0.0126 (5)	−0.0038 (5)	0.0302 (5)
O2	0.1033 (9)	0.0716 (7)	0.0721 (7)	0.0383 (6)	0.0486 (7)	0.0396 (6)
O3	0.0665 (6)	0.0570 (6)	0.0602 (6)	0.0274 (5)	0.0281 (5)	0.0204 (5)
N1	0.0516 (6)	0.0506 (6)	0.0567 (7)	0.0129 (5)	0.0173 (5)	0.0252 (5)
N2	0.0395 (5)	0.0447 (5)	0.0454 (5)	0.0100 (4)	0.0123 (4)	0.0157 (4)
C1	0.0346 (5)	0.0399 (5)	0.0369 (5)	0.0044 (4)	0.0046 (4)	0.0108 (4)
C2	0.0374 (5)	0.0404 (5)	0.0406 (6)	0.0067 (4)	0.0065 (4)	0.0114 (4)
C3	0.0460 (6)	0.0441 (6)	0.0541 (7)	0.0108 (5)	0.0121 (5)	0.0186 (5)
C4	0.0385 (5)	0.0477 (6)	0.0432 (6)	0.0088 (4)	0.0110 (4)	0.0103 (5)
C5	0.0411 (6)	0.0889 (11)	0.0523 (8)	0.0073 (7)	−0.0009 (6)	−0.0055 (7)
C6	0.0559 (8)	0.0873 (12)	0.0561 (9)	0.0050 (8)	0.0041 (7)	−0.0169 (8)
C7	0.0519 (7)	0.0856 (11)	0.0487 (8)	0.0122 (7)	0.0155 (6)	0.0000 (7)
C8	0.0382 (6)	0.0885 (11)	0.0556 (8)	0.0132 (6)	0.0064 (5)	−0.0025 (7)
C9	0.0371 (6)	0.0732 (9)	0.0508 (7)	0.0023 (6)	0.0061 (5)	−0.0066 (7)
C10	0.0382 (5)	0.0387 (5)	0.0358 (5)	0.0079 (4)	0.0045 (4)	0.0086 (4)
C11	0.0398 (5)	0.0452 (6)	0.0463 (6)	0.0042 (4)	−0.0009 (5)	0.0098 (5)
C12	0.0456 (6)	0.0515 (7)	0.0485 (7)	0.0114 (5)	−0.0056 (5)	0.0127 (5)
C13	0.0548 (7)	0.0409 (6)	0.0384 (6)	0.0121 (5)	0.0034 (5)	0.0110 (5)
C14	0.0466 (6)	0.0438 (6)	0.0536 (7)	0.0008 (5)	0.0007 (5)	0.0159 (5)
C15	0.0391 (5)	0.0485 (6)	0.0536 (7)	0.0045 (5)	−0.0016 (5)	0.0171 (6)
C16	0.0854 (11)	0.0509 (8)	0.0738 (10)	0.0118 (7)	0.0184 (8)	0.0292 (7)
C17	0.0428 (5)	0.0434 (6)	0.0428 (6)	0.0089 (4)	0.0073 (5)	0.0098 (5)
C18	0.0777 (10)	0.0834 (11)	0.0647 (10)	0.0400 (9)	0.0340 (8)	0.0200 (8)
C19	0.0807 (13)	0.167 (2)	0.0849 (15)	0.0658 (15)	0.0120 (11)	0.0140 (15)

Geometric parameters (Å, º) top

O1—C13	1.3590 (15)	C7—H7B	0.9700
O1—C16	1.421 (2)	C8—C9	1.5183 (19)
O2—C17	1.1962 (16)	C8—H8A	0.9700
O3—C17	1.3328 (15)	C8—H8B	0.9700
O3—C18	1.4463 (17)	C9—H9A	0.9700
N1—C3	1.3178 (16)	C9—H9B	0.9700
N1—N2	1.3598 (14)	C10—C15	1.3856 (16)
N2—C1	1.3551 (14)	C10—C11	1.3945 (16)
N2—C4	1.4657 (15)	C11—C12	1.3814 (17)
C1—C2	1.3917 (15)	C11—H11A	0.9300
C1—C10	1.4729 (15)	C12—C13	1.3849 (18)
C2—C3	1.4048 (16)	C12—H12A	0.9300
C2—C17	1.4611 (16)	C13—C14	1.3862 (18)
C3—H3A	0.9300	C14—C15	1.3840 (17)
C4—C9	1.5128 (17)	C14—H14A	0.9300
C4—C5	1.520 (2)	C15—H15A	0.9300
C4—H4A	0.9800	C16—H16A	0.9600
C5—C6	1.524 (2)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C18—C19	1.436 (3)
C6—C7	1.507 (2)	C18—H18A	0.9700
C6—H6A	0.9700	C18—H18B	0.9700
C6—H6B	0.9700	C19—H19A	0.9600
C7—C8	1.506 (2)	C19—H19B	0.9600
C7—H7A	0.9700	C19—H19C	0.9600

C13—O1—C16	117.95 (11)	C4—C9—C8	110.74 (12)
C17—O3—C18	116.56 (11)	C4—C9—H9A	109.5
C3—N1—N2	104.76 (10)	C8—C9—H9A	109.5
C1—N2—N1	112.70 (9)	C4—C9—H9B	109.5
C1—N2—C4	128.17 (10)	C8—C9—H9B	109.5
N1—N2—C4	119.08 (10)	H9A—C9—H9B	108.1
N2—C1—C2	105.63 (10)	C15—C10—C11	117.99 (10)
N2—C1—C10	122.86 (10)	C15—C10—C1	120.39 (10)
C2—C1—C10	131.51 (10)	C11—C10—C1	121.63 (10)
C1—C2—C3	105.00 (10)	C12—C11—C10	120.98 (11)
C1—C2—C17	127.24 (10)	C12—C11—H11A	119.5
C3—C2—C17	127.73 (11)	C10—C11—H11A	119.5
N1—C3—C2	111.91 (11)	C11—C12—C13	120.19 (11)
N1—C3—H3A	124.0	C11—C12—H12A	119.9
C2—C3—H3A	124.0	C13—C12—H12A	119.9
N2—C4—C9	110.98 (10)	O1—C13—C12	116.10 (11)
N2—C4—C5	111.32 (10)	O1—C13—C14	124.31 (12)
C9—C4—C5	110.76 (11)	C12—C13—C14	119.60 (11)
N2—C4—H4A	107.9	C15—C14—C13	119.71 (11)
C9—C4—H4A	107.9	C15—C14—H14A	120.1
C5—C4—H4A	107.9	C13—C14—H14A	120.1
C4—C5—C6	110.07 (12)	C14—C15—C10	121.53 (11)
C4—C5—H5A	109.6	C14—C15—H15A	119.2
C6—C5—H5A	109.6	C10—C15—H15A	119.2
C4—C5—H5B	109.6	O1—C16—H16A	109.5
C6—C5—H5B	109.6	O1—C16—H16B	109.5
H5A—C5—H5B	108.2	H16A—C16—H16B	109.5
C7—C6—C5	111.75 (14)	O1—C16—H16C	109.5
C7—C6—H6A	109.3	H16A—C16—H16C	109.5
C5—C6—H6A	109.3	H16B—C16—H16C	109.5
C7—C6—H6B	109.3	O2—C17—O3	122.85 (12)
C5—C6—H6B	109.3	O2—C17—C2	126.16 (12)
H6A—C6—H6B	107.9	O3—C17—C2	110.95 (10)
C8—C7—C6	111.45 (13)	C19—C18—O3	109.52 (15)
C8—C7—H7A	109.3	C19—C18—H18A	109.8
C6—C7—H7A	109.3	O3—C18—H18A	109.8
C8—C7—H7B	109.3	C19—C18—H18B	109.8
C6—C7—H7B	109.3	O3—C18—H18B	109.8
H7A—C7—H7B	108.0	H18A—C18—H18B	108.2
C7—C8—C9	111.41 (13)	C18—C19—H19A	109.5
C7—C8—H8A	109.3	C18—C19—H19B	109.5
C9—C8—H8A	109.3	H19A—C19—H19B	109.5
C7—C8—H8B	109.3	C18—C19—H19C	109.5
C9—C8—H8B	109.3	H19A—C19—H19C	109.5
H8A—C8—H8B	108.0	H19B—C19—H19C	109.5

C3—N1—N2—C1	−0.18 (14)	C7—C8—C9—C4	56.03 (19)
C3—N1—N2—C4	177.65 (11)	N2—C1—C10—C15	−114.31 (13)
N1—N2—C1—C2	0.28 (13)	C2—C1—C10—C15	64.46 (18)
C4—N2—C1—C2	−177.31 (11)	N2—C1—C10—C11	65.81 (16)
N1—N2—C1—C10	179.32 (10)	C2—C1—C10—C11	−115.41 (14)
C4—N2—C1—C10	1.74 (18)	C15—C10—C11—C12	0.16 (19)
N2—C1—C2—C3	−0.25 (13)	C1—C10—C11—C12	−179.97 (11)
C10—C1—C2—C3	−179.18 (12)	C10—C11—C12—C13	0.6 (2)
N2—C1—C2—C17	178.12 (11)	C16—O1—C13—C12	−173.91 (13)
C10—C1—C2—C17	−0.8 (2)	C16—O1—C13—C14	6.2 (2)
N2—N1—C3—C2	0.01 (15)	C11—C12—C13—O1	179.25 (12)
C1—C2—C3—N1	0.15 (15)	C11—C12—C13—C14	−0.9 (2)
C17—C2—C3—N1	−178.20 (12)	O1—C13—C14—C15	−179.74 (12)
C1—N2—C4—C9	−112.62 (14)	C12—C13—C14—C15	0.4 (2)
N1—N2—C4—C9	69.93 (15)	C13—C14—C15—C10	0.4 (2)
C1—N2—C4—C5	123.52 (14)	C11—C10—C15—C14	−0.64 (19)
N1—N2—C4—C5	−53.94 (15)	C1—C10—C15—C14	179.49 (11)
N2—C4—C5—C6	−179.09 (13)	C18—O3—C17—O2	−0.4 (2)
C9—C4—C5—C6	56.92 (18)	C18—O3—C17—C2	177.29 (13)
C4—C5—C6—C7	−55.8 (2)	C1—C2—C17—O2	−2.4 (2)
C5—C6—C7—C8	54.9 (2)	C3—C2—C17—O2	175.59 (15)
C6—C7—C8—C9	−54.7 (2)	C1—C2—C17—O3	−179.98 (11)
N2—C4—C9—C8	178.50 (12)	C3—C2—C17—O3	−1.97 (19)
C5—C4—C9—C8	−57.32 (17)	C17—O3—C18—C19	−149.67 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.96	2.44	3.358 (2)	159

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₃
M_r	328.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8959 (7), 11.0858 (7), 12.0142 (12)
α, β, γ (°)	100.690 (2), 93.107 (1), 95.354 (1)
V (Å³)	896.16 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.31 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18767, 5159, 3928
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.164, 1.05
No. of reflections	5159
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.9600	2.4400	3.358 (2)	159.00

Symmetry code: (i) −x, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malysia for the Research University Grant (No. 1001/PFIZIK/811160). AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.

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. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dhanya, S., Isloor, A. M. & Shetty, P. (2009). Der Pharm. Chem. 1, 19–26. Google Scholar
Fun, H.-K., Quah, C. K., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2010a). Acta Cryst. E66, o2228. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2010b). Acta Cryst. E66, o2282–o2283. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Malladi, S., Hebbar, R. & Isloor, A. M. (2011). Acta Cryst. E67, o3105. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hall, A., Billinton, A., Brown, S. H., Clayton, N. M., Chowdhury, A., Gerald, M. P., Goldsmith, G. P., Hayhow, T. G., Hurst, D. N., Kilford, I. R., Naylor, A. & Passingham, B. (2008). Bioorg. Med. Chem. Lett. 18, 3392–3399. Web of Science CrossRef PubMed CAS Google Scholar
Isloor, A. M., Kalluraya, B. & Rao, M. (2000). J. Saudi Chem. Soc. 4, 265–270. CAS Google Scholar
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784–3787. Web of Science CrossRef PubMed CAS Google Scholar
Premsai Rai, N., Narayanaswamy, V. K. & Shashikanth, S. (2009). Eur. J. Med. Chem. 44, 4522–4527. Web of Science PubMed Google Scholar
Ragavan, V., Vijay Kumar, V. & Kumari, S. N. (2010). Eur. J. Med. Chem. 45, 1173–1180. Web of Science CrossRef CAS PubMed 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