Diethyl 4-[2-(4-meth­oxy­phen­yl)-1H-pyrazol-3-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Fun, H.-K.; Hemamalini, M.; Vijesh, A.M.; Isloor, A.M.; Malladi, S.

doi:10.1107/S1600536811017600

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1417-o1418

doi:10.1107/S1600536811017600

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Diethyl 4-[2-(4-methoxyphenyl)-1H-pyrazol-3-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a A. M. Vijesh,^b § A. M. Isloor ^b and Shridhar Malladi ^b

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

(Received 3 May 2011; accepted 10 May 2011; online 14 May 2011)

In the title compound, C₂₃H₂₇N₃O₅, the pyrazole ring is inclined at dihedral angles of 38.16 (6) and 80.80 (6)°, respectively, to the least-squares planes of the benzene and dihydropyridine rings. In the crystal, adjacent molecules are linked via a pair of N—H⋯N hydrogen bonds, forming an inversion dimer. The dimers are stacked in a column along the a axis through N—H⋯O hydrogen bonds. Intra- and intermolecular C—H⋯N and C—H⋯O hydrogen bonds are also observed.

Related literature

For applications of pyridine derivatives, see: Surendra Kumar et al. (2011 ); Swarnalatha et al. (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₂₇N₃O₅
M_r = 425.48
Triclinic, $[P \overline 1]$
a = 8.5800 (1) Å
b = 11.1286 (1) Å
c = 11.4996 (1) Å
α = 94.425 (1)°
β = 99.191 (1)°
γ = 92.992 (1)°
V = 1078.37 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.39 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.965, T_max = 0.980
28279 measured reflections
7437 independent reflections
5974 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.134
S = 1.05
7437 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.906 (17)	1.981 (17)	2.8858 (12)	176.3 (14)
N1—H1N1⋯N3ⁱⁱ	0.880 (17)	2.173 (17)	2.9969 (13)	155.7 (16)
C6—H6B⋯N3ⁱⁱⁱ	0.98	2.50	3.4076 (15)	154
C7—H7A⋯O3^iv	0.98	2.59	3.5561 (15)	167
C14—H14A⋯N1	0.95	2.60	3.2484 (14)	126
C18—H18A⋯O1^v	0.95	2.48	3.1594 (14)	128
C22—H22A⋯O3	0.95	2.28	3.2210 (15)	170
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z+2.

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: 10.1107/S1600536811017600/is2709sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017600/is2709Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017600/is2709Isup3.cml

checkCIF report

Comment top

Substituted pyridines are important structural components of a variety of biologically active compounds. They possess anti-inflammatory, anti-microbial (Surendra Kumar et al., 2011), anti-oxidant, anti-tumor and anti-ulcer activities (Swarnalatha et al., 2011). In view of these activities, herein we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole (N2/N3/C14–C16) ring is approximately planar with maximum deviation of 0.003 (1) Å for atom N2. The central pyrazole (N2/N3/C14–C16) ring makes dihedral angles of 80.80 (6) and 38.16 (6)° with the pyridine (N1/C1–C5) ring and the benzene (C17–C22) ring, respectively. The dihedral angle between the pyridine (N1/C1–C5) ring and the benzene (C17–C22) ring is 44.88 (5)°.

In the crystal packing, (Fig. 2), the adjacent molecules are connected via intra- and intermolecular N2—H1N2···O1, N1—H1N1···N3, C6—H6B···N3, C7—H7A···O3, C14—H14A···N1, C18—H18A···O1 and C22—H22A···O3 hydrogen bonds.

Related literature top

For applications of pyridine derivatives, see: Surendra Kumar et al. (2011); Swarnalatha et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

3-(4-Methoxyphenyl)-1H-pyrazole-4-carbaldehyde (0.2g, 0.80 mmol), ethylacetoacetate (0.26g, 1.6 mmol) and ammonium acetate (0.07g, 0.90 mmol) in ethanol (20 ml) were refluxed for 8 hours in an oil bath. After the completion of the reaction, the reaction mixture was concentrated and poured into crushed ice. The precipitated product was filtered and washed with water. The resulting solid was recrystallized from hot ethanol (yield: 0.32g, 76%; m.p. 453–455 K).

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 and the atom-numbering scheme. C—H···O and C—H···N hydrogen bonds are shown by dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis.

Diethyl 4-[2-(4-methoxyphenyl)-1H-pyrazol-3-yl]-2,6-dimethyl- 1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₃H₂₇N₃O₅	Z = 2
M_r = 425.48	F(000) = 452
Triclinic, P1	D_x = 1.310 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5800 (1) Å	Cell parameters from 9992 reflections
b = 11.1286 (1) Å	θ = 2.4–32.9°
c = 11.4996 (1) Å	µ = 0.09 mm⁻¹
α = 94.425 (1)°	T = 100 K
β = 99.191 (1)°	Block, yellow
γ = 92.992 (1)°	0.39 × 0.23 × 0.22 mm
V = 1078.37 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7437 independent reflections
Radiation source: fine-focus sealed tube	5974 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 32.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.965, T_max = 0.980	k = −16→16
28279 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0684P)² + 0.3274P] where P = (F_o² + 2F_c²)/3
7437 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₂₇N₃O₅	γ = 92.992 (1)°
M_r = 425.48	V = 1078.37 (2) Å³
Triclinic, P1	Z = 2
a = 8.5800 (1) Å	Mo Kα radiation
b = 11.1286 (1) Å	µ = 0.09 mm⁻¹
c = 11.4996 (1) Å	T = 100 K
α = 94.425 (1)°	0.39 × 0.23 × 0.22 mm
β = 99.191 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7437 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5974 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.980	R_int = 0.022
28279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.51 e Å⁻³
7437 reflections	Δρ_min = −0.29 e Å⁻³
293 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.16548 (9)	0.44561 (8)	0.87653 (7)	0.02135 (17)
O2	0.38602 (9)	0.35073 (8)	0.93477 (7)	0.01969 (16)
O3	0.47154 (11)	0.01240 (8)	0.66212 (9)	0.0295 (2)
O4	0.25759 (10)	−0.00120 (7)	0.52149 (7)	0.02201 (17)
O5	0.90976 (11)	0.04691 (9)	1.17677 (8)	0.0292 (2)
N1	0.25821 (10)	0.36906 (8)	0.52613 (8)	0.01673 (17)
N2	0.83784 (11)	0.41106 (8)	0.76648 (8)	0.01671 (17)
N3	0.77514 (11)	0.47186 (9)	0.67396 (8)	0.01983 (18)
C1	0.29133 (12)	0.24919 (10)	0.50498 (9)	0.01684 (19)
C2	0.36451 (12)	0.19308 (9)	0.59735 (9)	0.01576 (18)
C3	0.43164 (11)	0.26769 (9)	0.71308 (9)	0.01462 (18)
H3A	0.4394	0.2133	0.7788	0.018*
C4	0.31145 (12)	0.36043 (9)	0.73257 (9)	0.01510 (18)
C5	0.24375 (12)	0.41694 (9)	0.63803 (9)	0.01594 (18)
C6	0.15830 (13)	0.53096 (10)	0.64023 (10)	0.0202 (2)
H6A	0.1846	0.5744	0.7190	0.030*
H6B	0.0439	0.5110	0.6218	0.030*
H6C	0.1905	0.5820	0.5813	0.030*
C7	0.23910 (14)	0.19722 (11)	0.37946 (9)	0.0223 (2)
H7A	0.3043	0.1305	0.3620	0.033*
H7B	0.2510	0.2600	0.3257	0.033*
H7C	0.1279	0.1672	0.3687	0.033*
C8	0.37462 (13)	0.06117 (10)	0.59670 (9)	0.01829 (19)
C9	0.25093 (15)	−0.13152 (10)	0.52548 (11)	0.0248 (2)
H9A	0.2395	−0.1533	0.6057	0.030*
H9B	0.3485	−0.1647	0.5043	0.030*
C10	0.10914 (15)	−0.18010 (11)	0.43720 (11)	0.0263 (2)
H10A	0.0967	−0.2680	0.4382	0.039*
H10B	0.1238	−0.1600	0.3580	0.039*
H10C	0.0143	−0.1440	0.4578	0.039*
C11	0.27844 (12)	0.39157 (9)	0.85152 (9)	0.01611 (18)
C12	0.36198 (14)	0.37357 (12)	1.05686 (10)	0.0241 (2)
H12A	0.2559	0.3404	1.0665	0.029*
H12B	0.3706	0.4614	1.0804	0.029*
C13	0.48935 (16)	0.31170 (14)	1.13135 (11)	0.0306 (3)
H13A	0.4835	0.3301	1.2152	0.046*
H13B	0.5933	0.3406	1.1158	0.046*
H13C	0.4741	0.2242	1.1115	0.046*
C14	0.62754 (12)	0.42337 (10)	0.64436 (10)	0.0191 (2)
H14A	0.5534	0.4484	0.5818	0.023*
C15	0.59282 (12)	0.33141 (9)	0.71527 (9)	0.01463 (18)
C16	0.73356 (12)	0.32572 (9)	0.79400 (9)	0.01473 (18)
C17	0.77961 (12)	0.25038 (9)	0.89185 (9)	0.01571 (18)
C18	0.87821 (13)	0.29968 (10)	0.99559 (9)	0.01787 (19)
H18A	0.9163	0.3820	1.0023	0.021*
C19	0.92046 (13)	0.22914 (11)	1.08843 (9)	0.0211 (2)
H19A	0.9872	0.2634	1.1583	0.025*
C20	0.86537 (13)	0.10797 (11)	1.07957 (10)	0.0216 (2)
C21	0.77058 (14)	0.05728 (11)	0.97597 (10)	0.0229 (2)
H21A	0.7349	−0.0256	0.9687	0.027*
C22	0.72820 (13)	0.12868 (10)	0.88280 (10)	0.0202 (2)
H22A	0.6634	0.0938	0.8123	0.024*
C23	0.85276 (17)	−0.07678 (13)	1.16952 (13)	0.0332 (3)
H23A	0.8849	−0.1095	1.2458	0.050*
H23B	0.8972	−0.1230	1.1081	0.050*
H23C	0.7371	−0.0827	1.1497	0.050*
H1N2	0.941 (2)	0.4250 (14)	0.7995 (14)	0.027 (4)*
H1N1	0.218 (2)	0.4093 (15)	0.4667 (15)	0.031 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0142 (4)	0.0257 (4)	0.0235 (4)	0.0027 (3)	0.0025 (3)	−0.0017 (3)
O2	0.0162 (4)	0.0277 (4)	0.0152 (3)	0.0038 (3)	0.0015 (3)	0.0024 (3)
O3	0.0270 (4)	0.0188 (4)	0.0375 (5)	0.0045 (3)	−0.0108 (4)	0.0004 (3)
O4	0.0196 (4)	0.0168 (4)	0.0268 (4)	−0.0008 (3)	−0.0033 (3)	0.0003 (3)
O5	0.0293 (5)	0.0338 (5)	0.0243 (4)	0.0007 (4)	−0.0021 (3)	0.0156 (4)
N1	0.0141 (4)	0.0181 (4)	0.0178 (4)	0.0012 (3)	0.0003 (3)	0.0051 (3)
N2	0.0121 (4)	0.0185 (4)	0.0191 (4)	0.0004 (3)	−0.0004 (3)	0.0056 (3)
N3	0.0141 (4)	0.0230 (4)	0.0225 (4)	0.0011 (3)	−0.0003 (3)	0.0096 (3)
C1	0.0130 (4)	0.0187 (5)	0.0182 (4)	−0.0013 (3)	0.0011 (3)	0.0019 (3)
C2	0.0130 (4)	0.0160 (4)	0.0177 (4)	−0.0001 (3)	0.0009 (3)	0.0010 (3)
C3	0.0120 (4)	0.0159 (4)	0.0158 (4)	0.0010 (3)	0.0012 (3)	0.0026 (3)
C4	0.0117 (4)	0.0158 (4)	0.0178 (4)	0.0005 (3)	0.0019 (3)	0.0026 (3)
C5	0.0109 (4)	0.0172 (4)	0.0196 (4)	−0.0002 (3)	0.0015 (3)	0.0033 (3)
C6	0.0165 (5)	0.0197 (5)	0.0249 (5)	0.0043 (4)	0.0020 (4)	0.0053 (4)
C7	0.0232 (5)	0.0254 (5)	0.0167 (4)	0.0007 (4)	−0.0012 (4)	0.0017 (4)
C8	0.0161 (5)	0.0174 (5)	0.0207 (5)	0.0002 (4)	0.0018 (4)	0.0002 (4)
C9	0.0244 (6)	0.0166 (5)	0.0314 (6)	0.0004 (4)	−0.0008 (4)	0.0011 (4)
C10	0.0231 (6)	0.0229 (5)	0.0307 (6)	−0.0012 (4)	0.0007 (4)	−0.0014 (4)
C11	0.0126 (4)	0.0160 (4)	0.0188 (4)	−0.0019 (3)	0.0006 (3)	0.0011 (3)
C12	0.0201 (5)	0.0360 (6)	0.0162 (5)	0.0006 (4)	0.0038 (4)	0.0005 (4)
C13	0.0261 (6)	0.0466 (8)	0.0188 (5)	0.0018 (5)	0.0006 (4)	0.0064 (5)
C14	0.0134 (4)	0.0225 (5)	0.0214 (5)	0.0011 (4)	−0.0003 (4)	0.0088 (4)
C15	0.0120 (4)	0.0156 (4)	0.0161 (4)	0.0009 (3)	0.0009 (3)	0.0030 (3)
C16	0.0135 (4)	0.0150 (4)	0.0156 (4)	0.0017 (3)	0.0014 (3)	0.0028 (3)
C17	0.0134 (4)	0.0174 (4)	0.0162 (4)	0.0020 (3)	0.0010 (3)	0.0031 (3)
C18	0.0162 (5)	0.0189 (5)	0.0178 (4)	0.0010 (4)	0.0004 (3)	0.0020 (4)
C19	0.0186 (5)	0.0264 (5)	0.0169 (4)	0.0009 (4)	−0.0019 (4)	0.0037 (4)
C20	0.0184 (5)	0.0268 (5)	0.0203 (5)	0.0026 (4)	0.0012 (4)	0.0103 (4)
C21	0.0212 (5)	0.0198 (5)	0.0263 (5)	−0.0013 (4)	−0.0023 (4)	0.0080 (4)
C22	0.0188 (5)	0.0194 (5)	0.0206 (5)	0.0001 (4)	−0.0030 (4)	0.0042 (4)
C23	0.0304 (6)	0.0343 (7)	0.0372 (7)	0.0016 (5)	0.0040 (5)	0.0219 (6)

Geometric parameters (Å, º) top

O1—C11	1.2275 (13)	C7—H7C	0.9800
O2—C11	1.3430 (12)	C9—C10	1.5017 (17)
O2—C12	1.4565 (13)	C9—H9A	0.9900
O3—C8	1.2093 (13)	C9—H9B	0.9900
O4—C8	1.3398 (13)	C10—H10A	0.9800
O4—C9	1.4530 (14)	C10—H10B	0.9800
O5—C20	1.3655 (13)	C10—H10C	0.9800
O5—C23	1.4282 (17)	C12—C13	1.5075 (17)
N1—C5	1.3810 (14)	C12—H12A	0.9900
N1—C1	1.3896 (14)	C12—H12B	0.9900
N1—H1N1	0.880 (17)	C13—H13A	0.9800
N2—N3	1.3584 (12)	C13—H13B	0.9800
N2—C16	1.3604 (13)	C13—H13C	0.9800
N2—H1N2	0.906 (17)	C14—C15	1.4056 (14)
N3—C14	1.3317 (14)	C14—H14A	0.9500
C1—C2	1.3574 (14)	C15—C16	1.3963 (14)
C1—C7	1.5021 (15)	C16—C17	1.4708 (13)
C2—C8	1.4746 (14)	C17—C22	1.3931 (15)
C2—C3	1.5254 (14)	C17—C18	1.4029 (14)
C3—C15	1.5165 (14)	C18—C19	1.3867 (14)
C3—C4	1.5258 (14)	C18—H18A	0.9500
C3—H3A	1.0000	C19—C20	1.3960 (17)
C4—C5	1.3627 (13)	C19—H19A	0.9500
C4—C11	1.4602 (14)	C20—C21	1.3921 (16)
C5—C6	1.4988 (15)	C21—C22	1.3959 (14)
C6—H6A	0.9800	C21—H21A	0.9500
C6—H6B	0.9800	C22—H22A	0.9500
C6—H6C	0.9800	C23—H23A	0.9800
C7—H7A	0.9800	C23—H23B	0.9800
C7—H7B	0.9800	C23—H23C	0.9800

C11—O2—C12	116.61 (8)	C9—C10—H10C	109.5
C8—O4—C9	115.93 (9)	H10A—C10—H10C	109.5
C20—O5—C23	116.58 (10)	H10B—C10—H10C	109.5
C5—N1—C1	121.27 (9)	O1—C11—O2	121.98 (10)
C5—N1—H1N1	116.6 (11)	O1—C11—C4	126.11 (9)
C1—N1—H1N1	119.6 (11)	O2—C11—C4	111.89 (9)
N3—N2—C16	112.67 (8)	O2—C12—C13	106.44 (10)
N3—N2—H1N2	120.6 (10)	O2—C12—H12A	110.4
C16—N2—H1N2	126.6 (10)	C13—C12—H12A	110.4
C14—N3—N2	103.98 (8)	O2—C12—H12B	110.4
C2—C1—N1	117.80 (9)	C13—C12—H12B	110.4
C2—C1—C7	127.83 (10)	H12A—C12—H12B	108.6
N1—C1—C7	114.37 (9)	C12—C13—H13A	109.5
C1—C2—C8	124.03 (9)	C12—C13—H13B	109.5
C1—C2—C3	119.30 (9)	H13A—C13—H13B	109.5
C8—C2—C3	116.54 (8)	C12—C13—H13C	109.5
C15—C3—C2	114.71 (8)	H13A—C13—H13C	109.5
C15—C3—C4	109.82 (8)	H13B—C13—H13C	109.5
C2—C3—C4	106.30 (8)	N3—C14—C15	113.01 (9)
C15—C3—H3A	108.6	N3—C14—H14A	123.5
C2—C3—H3A	108.6	C15—C14—H14A	123.5
C4—C3—H3A	108.6	C16—C15—C14	103.80 (9)
C5—C4—C11	121.66 (9)	C16—C15—C3	129.74 (9)
C5—C4—C3	118.34 (9)	C14—C15—C3	126.03 (9)
C11—C4—C3	119.91 (8)	N2—C16—C15	106.53 (9)
C4—C5—N1	118.28 (9)	N2—C16—C17	120.75 (9)
C4—C5—C6	127.35 (10)	C15—C16—C17	132.71 (9)
N1—C5—C6	114.32 (9)	C22—C17—C18	118.77 (9)
C5—C6—H6A	109.5	C22—C17—C16	120.81 (9)
C5—C6—H6B	109.5	C18—C17—C16	120.41 (9)
H6A—C6—H6B	109.5	C19—C18—C17	120.51 (10)
C5—C6—H6C	109.5	C19—C18—H18A	119.7
H6A—C6—H6C	109.5	C17—C18—H18A	119.7
H6B—C6—H6C	109.5	C18—C19—C20	120.28 (10)
C1—C7—H7A	109.5	C18—C19—H19A	119.9
C1—C7—H7B	109.5	C20—C19—H19A	119.9
H7A—C7—H7B	109.5	O5—C20—C21	124.32 (11)
C1—C7—H7C	109.5	O5—C20—C19	115.95 (10)
H7A—C7—H7C	109.5	C21—C20—C19	119.73 (10)
H7B—C7—H7C	109.5	C20—C21—C22	119.77 (10)
O3—C8—O4	122.38 (10)	C20—C21—H21A	120.1
O3—C8—C2	124.30 (10)	C22—C21—H21A	120.1
O4—C8—C2	113.15 (9)	C17—C22—C21	120.91 (10)
O4—C9—C10	106.00 (9)	C17—C22—H22A	119.5
O4—C9—H9A	110.5	C21—C22—H22A	119.5
C10—C9—H9A	110.5	O5—C23—H23A	109.5
O4—C9—H9B	110.5	O5—C23—H23B	109.5
C10—C9—H9B	110.5	H23A—C23—H23B	109.5
H9A—C9—H9B	108.7	O5—C23—H23C	109.5
C9—C10—H10A	109.5	H23A—C23—H23C	109.5
C9—C10—H10B	109.5	H23B—C23—H23C	109.5
H10A—C10—H10B	109.5

C16—N2—N3—C14	0.59 (12)	C5—C4—C11—O2	−163.27 (9)
C5—N1—C1—C2	−23.57 (14)	C3—C4—C11—O2	13.14 (13)
C5—N1—C1—C7	156.10 (10)	C11—O2—C12—C13	175.86 (10)
N1—C1—C2—C8	165.32 (10)	N2—N3—C14—C15	−0.41 (13)
C7—C1—C2—C8	−14.30 (17)	N3—C14—C15—C16	0.10 (13)
N1—C1—C2—C3	−10.26 (14)	N3—C14—C15—C3	173.13 (10)
C7—C1—C2—C3	170.12 (10)	C2—C3—C15—C16	−124.23 (11)
C1—C2—C3—C15	−81.50 (12)	C4—C3—C15—C16	116.16 (11)
C8—C2—C3—C15	102.59 (10)	C2—C3—C15—C14	64.59 (14)
C1—C2—C3—C4	40.06 (12)	C4—C3—C15—C14	−55.03 (13)
C8—C2—C3—C4	−135.85 (9)	N3—N2—C16—C15	−0.54 (12)
C15—C3—C4—C5	82.46 (11)	N3—N2—C16—C17	−179.99 (9)
C2—C3—C4—C5	−42.18 (12)	C14—C15—C16—N2	0.26 (11)
C15—C3—C4—C11	−94.07 (11)	C3—C15—C16—N2	−172.41 (10)
C2—C3—C4—C11	141.30 (9)	C14—C15—C16—C17	179.61 (11)
C11—C4—C5—N1	−168.89 (9)	C3—C15—C16—C17	6.94 (19)
C3—C4—C5—N1	14.65 (14)	N2—C16—C17—C22	−141.80 (11)
C11—C4—C5—C6	13.84 (16)	C15—C16—C17—C22	38.92 (17)
C3—C4—C5—C6	−162.62 (10)	N2—C16—C17—C18	37.31 (15)
C1—N1—C5—C4	21.24 (14)	C15—C16—C17—C18	−141.96 (12)
C1—N1—C5—C6	−161.14 (9)	C22—C17—C18—C19	−1.53 (16)
C9—O4—C8—O3	1.75 (17)	C16—C17—C18—C19	179.34 (10)
C9—O4—C8—C2	−173.77 (9)	C17—C18—C19—C20	0.08 (17)
C1—C2—C8—O3	159.34 (12)	C23—O5—C20—C21	−0.38 (18)
C3—C2—C8—O3	−24.97 (16)	C23—O5—C20—C19	179.30 (11)
C1—C2—C8—O4	−25.24 (15)	C18—C19—C20—O5	−178.22 (10)
C3—C2—C8—O4	150.45 (9)	C18—C19—C20—C21	1.47 (18)
C8—O4—C9—C10	178.33 (10)	O5—C20—C21—C22	178.13 (11)
C12—O2—C11—O1	0.11 (15)	C19—C20—C21—C22	−1.54 (18)
C12—O2—C11—C4	−178.22 (9)	C18—C17—C22—C21	1.46 (17)
C5—C4—C11—O1	18.49 (17)	C16—C17—C22—C21	−179.41 (10)
C3—C4—C11—O1	−165.10 (10)	C20—C21—C22—C17	0.06 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.906 (17)	1.981 (17)	2.8858 (12)	176.3 (14)
N1—H1N1···N3ⁱⁱ	0.880 (17)	2.173 (17)	2.9969 (13)	155.7 (16)
C6—H6B···N3ⁱⁱⁱ	0.98	2.50	3.4076 (15)	154
C7—H7A···O3^iv	0.98	2.59	3.5561 (15)	167
C14—H14A···N1	0.95	2.60	3.2484 (14)	126
C18—H18A···O1^v	0.95	2.48	3.1594 (14)	128
C22—H22A···O3	0.95	2.28	3.2210 (15)	170

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₇N₃O₅
M_r	425.48
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.5800 (1), 11.1286 (1), 11.4996 (1)
α, β, γ (°)	94.425 (1), 99.191 (1), 92.992 (1)
V (Å³)	1078.37 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.965, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	28279, 7437, 5974
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.134, 1.05
No. of reflections	7437
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.29

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
N2—H1N2···O1ⁱ	0.906 (17)	1.981 (17)	2.8858 (12)	176.3 (14)
N1—H1N1···N3ⁱⁱ	0.880 (17)	2.173 (17)	2.9969 (13)	155.7 (16)
C6—H6B···N3ⁱⁱⁱ	0.98	2.50	3.4076 (15)	154
C7—H7A···O3^iv	0.98	2.59	3.5561 (15)	167
C14—H14A···N1	0.95	2.60	3.2484 (14)	126
C18—H18A···O1^v	0.95	2.48	3.1594 (14)	128
C22—H22A···O3	0.95	2.28	3.2210 (15)	170

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§On secondment to: SeQuent Scientific Ltd, No. 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka 575 011, India.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. AMI thanks the Board for Research in Nuclear Sciences, Government of India, for a Young Scientists award. AMV is thankful to Dr Arulmoli, Vice President (R&D) and the management, SeQuent Scientific Ltd, New Mangalore, India, for their invaluable support and allocation of resources for this work.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science 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
Surendra Kumar, R., Idhayadhulla, A., Jamal Abdul Nasser, A. & Selvin, J. (2011). J. Serb. Chem. Soc. 76, 1–11. Google Scholar
Swarnalatha, G., Prasanthi, G., Sirisha, N. & Madhusudhana Chetty, C. (2011). Int. J. ChemTech Res. 3, 75–89. CAS Google Scholar

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Volume 67| Part 6| June 2011| Pages o1417-o1418

doi:10.1107/S1600536811017600

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

Di­ethyl 4-[2-(4-meth­­oxy­phen­yl)-1H-pyrazol-3-yl]-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Diethyl 4-[2-(4-methoxyphenyl)-1H-pyrazol-3-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate