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

Fun, H.-K.; Ooi, C.W.; Garudachari, B.; Shivananda, K.N.; Isloor, A.M.

doi:10.1107/S1600536812027936

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2210-o2211

https://doi.org/10.1107/S1600536812027936

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

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a B. Garudachari,^b Kammasandra Nanjunda Shivananda ^c and Arun M. Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bMedicinal Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Mangalore 575 025, India, and ^cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel
^*Correspondence e-mail: hkfun@usm.my

(Received 18 June 2012; accepted 20 June 2012; online 27 June 2012)

In the title compound, C₂₇H₂₇N₃O₅·2H₂O, the dihydropyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, molecules are linked via N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C—H⋯π interactions.

Related literature

For details and applications of pyrazoles, see: Buhler & Kiowski (1987 ); Isloor et al. (2000 , 2009 ); Isloor (2011 ); Vijesh et al. (2011 ); Vo et al. (1995 ). For the preparation of the compound, see: Trivedi et al. (2011 ). For ring conformations, see: Cremer & Pople (1975 ). For related structures, see: Fun et al. (2011 , 2012 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₇H₂₇N₃O₅·2H₂O
M_r = 509.55
Monoclinic, P 2₁ /c
a = 14.1279 (9) Å
b = 11.6313 (7) Å
c = 15.3780 (9) Å
β = 93.358 (1)°
V = 2522.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.34 × 0.17 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.987
28375 measured reflections
7347 independent reflections
5683 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.131
S = 1.04
7347 reflections
359 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the pyrazole (N2/N3/C6–C8) and benzene (C15–C20) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2W	0.904 (18)	2.001 (18)	2.9020 (14)	175.2 (15)
O1W—H2W1⋯N3	0.90 (2)	2.05 (2)	2.9449 (14)	174 (2)
O2W—H2W2⋯O1Wⁱ	0.98 (3)	1.84 (3)	2.7986 (15)	166 (2)
O2W—H1W2⋯O3ⁱⁱ	0.90 (3)	1.91 (3)	2.8074 (14)	174 (2)
O1W—H1W1⋯O2Wⁱⁱⁱ	0.87 (3)	2.06 (3)	2.9274 (15)	178 (2)
C20—H20A⋯O1W^iv	0.95	2.44	3.2980 (16)	151
C13—H13A⋯Cg2^v	0.95	2.90	3.6957 (14)	142
C18—H18A⋯Cg1^vi	0.95	2.63	3.3682 (15)	135
C25—H25A⋯Cg2ⁱ	0.98	2.87	3.7231 (14)	146
C27—H27C⋯Cg1^v	0.98	2.62	3.5720 (17)	164
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536812027936/sj5244sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027936/sj5244Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027936/sj5244Isup3.cml

checkCIF report

Comment top

In the recent years, pyrazoles and their derivatives have attracted medicinal chemists because of their varied biological properties such as anti-microbial (Isloor et al., 2009), analgesic (Isloor et al., 2000; Isloor, 2011) and anti-inflammatory (Vijesh et al., 2011) activities. They are used most frequently as cardiovascular agents for the treatment of hypertension (Buhler & Kiowski, 1987). A number of dihydropyridine (DHP) derivatives are employed as potential drug candidates for the treatment of congestive heart failure (Vo et al., 1995). In view of this potential biological importance, we have synthesised the title DHP compound and report its structure here.

The asymmetric unit of the title compound (Fig. 1), contains one dimethyl 4-[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate molecule and two water molecules. The dihydropyridine (N1/C1–C5) ring adopts a flattened boat conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.3369 (12) Å, θ = 107.1 (2)°, and φ = 1.5 (2)°. The central pyrazole ring (N2/N3/C6–C8) is essentially planar [maximum deviation of 0.003 (1) Å at atoms N2 and C8] and makes dihedral angles of 50.42 (6)° and 26.44 (6)°, respectively, with the benzene rings (C9–C14 & C15–C20). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those found in related structures (Fun et al., 2011, 2012).

In the crystal structure (Fig. 2), the molecules are linked via intermolecular N1—H1N1···O2W, O1W—H1W1···O2W, O1W—H2W1···N3, O2W—H1W2···O3, O2W—H2W2···O1W and C20—H20A···O1W hydrogen bonds (Table 1) into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C—H···π interactions (Table 1), involving the centroids of the pyrazole ring (N2/N3/C6–C8; Cg1) and benzene ring (C15–C20; Cg2).

Related literature top

For details and applications of pyrazoles, see: Buhler & Kiowski (1987); Isloor et al. (2000, 2009); Isloor (2011); Vijesh et al. (2011); Vo et al. (1995). For the preparation of the compound, see: Trivedi et al. (2011). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2011, 2012). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (0.20 g, 0.0007 mol), acetyl acetone (0.17 g, 0.0015 mol) and ammonium acetate (0.064 g, 0.00084 mol) in ethanol (10 ml) were refluxed for 5 h. 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 ethanol. Yield: 0.28 g, 82.3%; M.p. 393–395 K. (Trivedi et al., 2011).

Structure description top

For details and applications of pyrazoles, see: Buhler & Kiowski (1987); Isloor et al. (2000, 2009); Isloor (2011); Vijesh et al. (2011); Vo et al. (1995). For the preparation of the compound, see: Trivedi et al. (2011). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2011, 2012). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

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

Crystal data top

C₂₇H₂₇N₃O₅·2H₂O	F(000) = 1080
M_r = 509.55	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7658 reflections
a = 14.1279 (9) Å	θ = 2.3–30.0°
b = 11.6313 (7) Å	µ = 0.10 mm⁻¹
c = 15.3780 (9) Å	T = 100 K
β = 93.358 (1)°	Block, yellow
V = 2522.7 (3) Å³	0.34 × 0.17 × 0.14 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7347 independent reflections
Radiation source: fine-focus sealed tube	5683 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 30.1°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.968, T_max = 0.987	k = −16→13
28375 measured reflections	l = −21→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0713P)² + 0.6924P] where P = (F_o² + 2F_c²)/3
7347 reflections	(Δ/σ)_max < 0.001
359 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₇H₂₇N₃O₅·2H₂O	V = 2522.7 (3) Å³
M_r = 509.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1279 (9) Å	µ = 0.10 mm⁻¹
b = 11.6313 (7) Å	T = 100 K
c = 15.3780 (9) Å	0.34 × 0.17 × 0.14 mm
β = 93.358 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7347 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5683 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.987	R_int = 0.036
28375 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
7347 reflections	Δρ_min = −0.24 e Å⁻³
359 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 (1) K.

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	−0.00103 (7)	0.62548 (9)	0.37770 (6)	0.0226 (2)
O1W	0.41969 (8)	0.86761 (10)	−0.00494 (6)	0.0234 (2)
O2	0.03130 (6)	0.66323 (8)	0.23892 (6)	0.01912 (19)
O2W	0.38758 (7)	0.38977 (8)	0.53450 (6)	0.0195 (2)
O3	0.28443 (7)	0.24426 (8)	0.14770 (6)	0.0219 (2)
O4	0.18314 (7)	0.37519 (8)	0.08778 (6)	0.0200 (2)
O5	0.08804 (7)	0.56032 (9)	−0.20791 (6)	0.0225 (2)
N1	0.25743 (8)	0.42928 (9)	0.38442 (6)	0.0156 (2)
N2	0.34896 (7)	0.74941 (9)	0.22034 (6)	0.01294 (19)
N3	0.32317 (7)	0.74721 (9)	0.13320 (6)	0.0136 (2)
C1	0.13336 (8)	0.53784 (10)	0.31548 (7)	0.0133 (2)
C2	0.17983 (8)	0.50147 (11)	0.39019 (7)	0.0144 (2)
C3	0.27622 (8)	0.36991 (10)	0.30988 (7)	0.0141 (2)
C4	0.23111 (8)	0.40222 (10)	0.23297 (7)	0.0129 (2)
C5	0.17563 (8)	0.51489 (10)	0.22856 (7)	0.0120 (2)
H5A	0.1231	0.5084	0.1824	0.014*
C6	0.23963 (8)	0.61354 (10)	0.20620 (7)	0.0123 (2)
C7	0.25677 (8)	0.66432 (10)	0.12467 (7)	0.0125 (2)
C8	0.29982 (8)	0.67097 (10)	0.26530 (7)	0.0132 (2)
H8A	0.3058	0.6580	0.3264	0.016*
C9	0.21375 (9)	0.63618 (10)	0.03755 (7)	0.0141 (2)
C10	0.11507 (9)	0.62914 (11)	0.02224 (8)	0.0162 (2)
H10A	0.0751	0.6420	0.0688	0.019*
C11	0.07515 (9)	0.60366 (12)	−0.05989 (8)	0.0182 (2)
H11A	0.0082	0.5994	−0.0694	0.022*
C12	0.13333 (9)	0.58421 (11)	−0.12869 (7)	0.0172 (2)
C13	0.23124 (9)	0.58855 (12)	−0.11424 (8)	0.0186 (3)
H13A	0.2712	0.5736	−0.1606	0.022*
C14	0.27062 (9)	0.61488 (11)	−0.03141 (8)	0.0167 (2)
H14A	0.3376	0.6183	−0.0219	0.020*
C15	0.41077 (8)	0.83539 (10)	0.25672 (7)	0.0134 (2)
C16	0.42022 (9)	0.93974 (11)	0.21407 (8)	0.0175 (2)
H16A	0.3877	0.9529	0.1591	0.021*
C17	0.47758 (10)	1.02438 (12)	0.25260 (9)	0.0223 (3)
H17A	0.4849	1.0955	0.2234	0.027*
C18	0.52447 (10)	1.00658 (12)	0.33343 (9)	0.0226 (3)
H18A	0.5631	1.0654	0.3596	0.027*
C19	0.51448 (9)	0.90238 (12)	0.37554 (8)	0.0190 (3)
H19A	0.5464	0.8899	0.4308	0.023*
C20	0.45806 (9)	0.81588 (11)	0.33746 (7)	0.0155 (2)
H20A	0.4518	0.7442	0.3662	0.019*
C21	0.23800 (9)	0.33188 (11)	0.15483 (7)	0.0150 (2)
C22	0.17954 (12)	0.30966 (13)	0.00848 (9)	0.0288 (3)
H22A	0.1412	0.3508	−0.0367	0.043*
H22B	0.1510	0.2344	0.0186	0.043*
H22C	0.2439	0.2991	−0.0106	0.043*
C23	0.04876 (9)	0.61105 (11)	0.31701 (8)	0.0158 (2)
C24	−0.05368 (10)	0.73192 (13)	0.23212 (9)	0.0244 (3)
H24A	−0.0586	0.7705	0.1754	0.037*
H24B	−0.0512	0.7897	0.2786	0.037*
H24C	−0.1091	0.6823	0.2378	0.037*
C25	0.34522 (9)	0.27246 (12)	0.32367 (8)	0.0195 (3)
H25A	0.3937	0.2775	0.2807	0.029*
H25B	0.3114	0.1992	0.3167	0.029*
H25C	0.3756	0.2772	0.3825	0.029*
C26	0.15698 (10)	0.53149 (12)	0.48159 (8)	0.0204 (3)
H26A	0.1351	0.6114	0.4835	0.031*
H26B	0.2139	0.5224	0.5205	0.031*
H26C	0.1070	0.4803	0.5004	0.031*
C27	0.14331 (11)	0.56823 (14)	−0.28286 (8)	0.0267 (3)
H27A	0.1017	0.5606	−0.3358	0.040*
H27B	0.1907	0.5066	−0.2810	0.040*
H27C	0.1754	0.6429	−0.2830	0.040*
H1N1	0.2957 (13)	0.4137 (15)	0.4321 (12)	0.027 (4)*
H2W1	0.3944 (16)	0.828 (2)	0.0380 (14)	0.047 (6)*
H2W2	0.4530 (18)	0.3690 (19)	0.5247 (14)	0.052 (6)*
H1W1	0.4089 (18)	0.939 (2)	0.0070 (16)	0.063 (7)*
H1W2	0.3581 (17)	0.345 (2)	0.5726 (15)	0.053 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (5)	0.0257 (5)	0.0230 (4)	0.0020 (4)	0.0086 (4)	−0.0036 (4)
O1W	0.0300 (5)	0.0186 (5)	0.0229 (5)	−0.0027 (4)	0.0110 (4)	−0.0019 (4)
O2	0.0167 (4)	0.0197 (5)	0.0212 (4)	0.0060 (4)	0.0028 (3)	0.0014 (3)
O2W	0.0218 (5)	0.0177 (5)	0.0190 (4)	−0.0011 (4)	0.0007 (3)	0.0042 (3)
O3	0.0258 (5)	0.0186 (5)	0.0216 (4)	0.0060 (4)	0.0035 (4)	−0.0049 (3)
O4	0.0297 (5)	0.0170 (5)	0.0133 (4)	0.0042 (4)	0.0004 (3)	−0.0036 (3)
O5	0.0245 (5)	0.0303 (5)	0.0126 (4)	−0.0096 (4)	−0.0004 (3)	−0.0005 (3)
N1	0.0166 (5)	0.0170 (5)	0.0132 (4)	0.0014 (4)	0.0010 (4)	0.0005 (4)
N2	0.0147 (5)	0.0121 (5)	0.0119 (4)	−0.0009 (4)	0.0005 (3)	0.0001 (3)
N3	0.0153 (5)	0.0141 (5)	0.0115 (4)	−0.0002 (4)	0.0010 (3)	0.0005 (3)
C1	0.0135 (5)	0.0126 (5)	0.0142 (5)	−0.0020 (4)	0.0048 (4)	−0.0015 (4)
C2	0.0155 (5)	0.0134 (6)	0.0146 (5)	−0.0026 (4)	0.0044 (4)	−0.0006 (4)
C3	0.0140 (5)	0.0124 (6)	0.0162 (5)	−0.0012 (4)	0.0033 (4)	0.0000 (4)
C4	0.0130 (5)	0.0114 (5)	0.0147 (5)	−0.0010 (4)	0.0035 (4)	−0.0011 (4)
C5	0.0123 (5)	0.0117 (5)	0.0123 (5)	−0.0005 (4)	0.0022 (4)	−0.0001 (4)
C6	0.0131 (5)	0.0114 (5)	0.0126 (5)	0.0008 (4)	0.0023 (4)	0.0000 (4)
C7	0.0128 (5)	0.0113 (5)	0.0134 (5)	0.0008 (4)	0.0022 (4)	0.0001 (4)
C8	0.0150 (5)	0.0119 (5)	0.0130 (5)	−0.0005 (4)	0.0025 (4)	0.0004 (4)
C9	0.0165 (5)	0.0129 (6)	0.0130 (5)	−0.0013 (4)	0.0009 (4)	0.0016 (4)
C10	0.0154 (6)	0.0186 (6)	0.0148 (5)	0.0006 (5)	0.0027 (4)	0.0015 (4)
C11	0.0164 (6)	0.0206 (6)	0.0175 (5)	−0.0022 (5)	0.0000 (4)	0.0016 (4)
C12	0.0208 (6)	0.0173 (6)	0.0133 (5)	−0.0050 (5)	0.0002 (4)	0.0010 (4)
C13	0.0196 (6)	0.0229 (7)	0.0138 (5)	−0.0044 (5)	0.0044 (4)	−0.0016 (4)
C14	0.0150 (5)	0.0196 (6)	0.0155 (5)	−0.0034 (5)	0.0026 (4)	0.0003 (4)
C15	0.0126 (5)	0.0124 (6)	0.0153 (5)	−0.0008 (4)	0.0030 (4)	−0.0016 (4)
C16	0.0205 (6)	0.0156 (6)	0.0166 (5)	−0.0027 (5)	0.0027 (4)	0.0014 (4)
C17	0.0265 (7)	0.0173 (6)	0.0235 (6)	−0.0076 (5)	0.0037 (5)	0.0009 (5)
C18	0.0218 (6)	0.0218 (7)	0.0243 (6)	−0.0091 (5)	0.0023 (5)	−0.0043 (5)
C19	0.0155 (6)	0.0227 (7)	0.0187 (5)	−0.0025 (5)	0.0005 (4)	−0.0021 (5)
C20	0.0147 (5)	0.0151 (6)	0.0168 (5)	−0.0001 (4)	0.0020 (4)	−0.0001 (4)
C21	0.0152 (5)	0.0141 (6)	0.0161 (5)	−0.0024 (4)	0.0042 (4)	−0.0006 (4)
C22	0.0461 (9)	0.0240 (7)	0.0158 (6)	0.0082 (6)	−0.0015 (5)	−0.0069 (5)
C23	0.0149 (5)	0.0143 (6)	0.0183 (5)	−0.0019 (4)	0.0033 (4)	−0.0018 (4)
C24	0.0187 (6)	0.0235 (7)	0.0307 (7)	0.0075 (5)	−0.0007 (5)	−0.0011 (5)
C25	0.0203 (6)	0.0180 (6)	0.0203 (6)	0.0050 (5)	0.0023 (4)	0.0015 (4)
C26	0.0243 (6)	0.0227 (7)	0.0146 (5)	0.0020 (5)	0.0048 (4)	−0.0013 (4)
C27	0.0315 (7)	0.0350 (8)	0.0139 (5)	−0.0139 (6)	0.0034 (5)	−0.0020 (5)

Geometric parameters (Å, º) top

O1—C23	1.2129 (15)	C10—C11	1.3848 (16)
O1W—H2W1	0.89 (2)	C10—H10A	0.9500
O1W—H1W1	0.87 (3)	C11—C12	1.3957 (18)
O2—C23	1.3553 (15)	C11—H11A	0.9500
O2—C24	1.4408 (15)	C12—C13	1.3890 (18)
O2W—H2W2	0.98 (2)	C13—C14	1.3939 (16)
O2W—H1W2	0.90 (3)	C13—H13A	0.9500
O3—C21	1.2204 (16)	C14—H14A	0.9500
O4—C21	1.3507 (14)	C15—C16	1.3897 (17)
O4—C22	1.4364 (15)	C15—C20	1.3936 (15)
O5—C12	1.3709 (14)	C16—C17	1.3859 (18)
O5—C27	1.4324 (16)	C16—H16A	0.9500
N1—C3	1.3773 (15)	C17—C18	1.3894 (18)
N1—C2	1.3879 (16)	C17—H17A	0.9500
N1—H1N1	0.904 (18)	C18—C19	1.3853 (19)
N2—C8	1.3596 (15)	C18—H18A	0.9500
N2—N3	1.3683 (13)	C19—C20	1.3915 (17)
N2—C15	1.4207 (15)	C19—H19A	0.9500
N3—C7	1.3463 (15)	C20—H20A	0.9500
C1—C2	1.3570 (15)	C22—H22A	0.9800
C1—C23	1.4688 (17)	C22—H22B	0.9800
C1—C5	1.5192 (15)	C22—H22C	0.9800
C2—C26	1.5015 (16)	C24—H24A	0.9800
C3—C4	1.3630 (15)	C24—H24B	0.9800
C3—C25	1.5018 (17)	C24—H24C	0.9800
C4—C21	1.4616 (16)	C25—H25A	0.9800
C4—C5	1.5266 (16)	C25—H25B	0.9800
C5—C6	1.5129 (16)	C25—H25C	0.9800
C5—H5A	1.0000	C26—H26A	0.9800
C6—C8	1.3801 (15)	C26—H26B	0.9800
C6—C7	1.4194 (15)	C26—H26C	0.9800
C7—C9	1.4751 (15)	C27—H27A	0.9800
C8—H8A	0.9500	C27—H27B	0.9800
C9—C14	1.3897 (17)	C27—H27C	0.9800
C9—C10	1.4026 (17)

H2W1—O1W—H1W1	105 (2)	C13—C14—H14A	119.4
C23—O2—C24	114.85 (10)	C16—C15—C20	120.56 (11)
H2W2—O2W—H1W2	116 (2)	C16—C15—N2	120.19 (10)
C21—O4—C22	116.13 (10)	C20—C15—N2	119.19 (11)
C12—O5—C27	117.00 (10)	C17—C16—C15	119.25 (11)
C3—N1—C2	123.24 (10)	C17—C16—H16A	120.4
C3—N1—H1N1	116.1 (11)	C15—C16—H16A	120.4
C2—N1—H1N1	120.4 (11)	C16—C17—C18	120.85 (12)
C8—N2—N3	111.77 (9)	C16—C17—H17A	119.6
C8—N2—C15	126.34 (10)	C18—C17—H17A	119.6
N3—N2—C15	121.40 (10)	C19—C18—C17	119.50 (12)
C7—N3—N2	104.64 (9)	C19—C18—H18A	120.3
C2—C1—C23	121.39 (11)	C17—C18—H18A	120.3
C2—C1—C5	119.64 (10)	C18—C19—C20	120.49 (11)
C23—C1—C5	118.56 (10)	C18—C19—H19A	119.8
C1—C2—N1	118.63 (10)	C20—C19—H19A	119.8
C1—C2—C26	126.88 (11)	C19—C20—C15	119.35 (12)
N1—C2—C26	114.48 (10)	C19—C20—H20A	120.3
C4—C3—N1	118.73 (11)	C15—C20—H20A	120.3
C4—C3—C25	126.67 (11)	O3—C21—O4	122.02 (11)
N1—C3—C25	114.59 (10)	O3—C21—C4	127.11 (11)
C3—C4—C21	120.58 (11)	O4—C21—C4	110.86 (10)
C3—C4—C5	119.21 (10)	O4—C22—H22A	109.5
C21—C4—C5	120.18 (10)	O4—C22—H22B	109.5
C6—C5—C1	109.73 (9)	H22A—C22—H22B	109.5
C6—C5—C4	110.43 (9)	O4—C22—H22C	109.5
C1—C5—C4	109.81 (9)	H22A—C22—H22C	109.5
C6—C5—H5A	108.9	H22B—C22—H22C	109.5
C1—C5—H5A	108.9	O1—C23—O2	122.43 (11)
C4—C5—H5A	108.9	O1—C23—C1	127.00 (11)
C8—C6—C7	104.47 (10)	O2—C23—C1	110.58 (10)
C8—C6—C5	124.81 (10)	O2—C24—H24A	109.5
C7—C6—C5	130.65 (10)	O2—C24—H24B	109.5
N3—C7—C6	111.46 (10)	H24A—C24—H24B	109.5
N3—C7—C9	119.67 (10)	O2—C24—H24C	109.5
C6—C7—C9	128.86 (11)	H24A—C24—H24C	109.5
N2—C8—C6	107.65 (10)	H24B—C24—H24C	109.5
N2—C8—H8A	126.2	C3—C25—H25A	109.5
C6—C8—H8A	126.2	C3—C25—H25B	109.5
C14—C9—C10	118.35 (10)	H25A—C25—H25B	109.5
C14—C9—C7	120.45 (11)	C3—C25—H25C	109.5
C10—C9—C7	121.20 (11)	H25A—C25—H25C	109.5
C11—C10—C9	120.89 (11)	H25B—C25—H25C	109.5
C11—C10—H10A	119.6	C2—C26—H26A	109.5
C9—C10—H10A	119.6	C2—C26—H26B	109.5
C10—C11—C12	119.97 (11)	H26A—C26—H26B	109.5
C10—C11—H11A	120.0	C2—C26—H26C	109.5
C12—C11—H11A	120.0	H26A—C26—H26C	109.5
O5—C12—C13	123.92 (11)	H26B—C26—H26C	109.5
O5—C12—C11	116.20 (11)	O5—C27—H27A	109.5
C13—C12—C11	119.87 (11)	O5—C27—H27B	109.5
C12—C13—C14	119.64 (11)	H27A—C27—H27B	109.5
C12—C13—H13A	120.2	O5—C27—H27C	109.5
C14—C13—H13A	120.2	H27A—C27—H27C	109.5
C9—C14—C13	121.26 (11)	H27B—C27—H27C	109.5
C9—C14—H14A	119.4

C8—N2—N3—C7	−0.45 (13)	N3—C7—C9—C10	−130.42 (13)
C15—N2—N3—C7	−172.90 (10)	C6—C7—C9—C10	50.89 (18)
C23—C1—C2—N1	177.85 (11)	C14—C9—C10—C11	−1.15 (19)
C5—C1—C2—N1	−9.57 (17)	C7—C9—C10—C11	179.43 (12)
C23—C1—C2—C26	−2.5 (2)	C9—C10—C11—C12	0.2 (2)
C5—C1—C2—C26	170.03 (12)	C27—O5—C12—C13	−15.73 (19)
C3—N1—C2—C1	−16.56 (18)	C27—O5—C12—C11	164.95 (12)
C3—N1—C2—C26	163.79 (11)	C10—C11—C12—O5	−179.56 (12)
C2—N1—C3—C4	15.78 (18)	C10—C11—C12—C13	1.1 (2)
C2—N1—C3—C25	−163.19 (11)	O5—C12—C13—C14	179.27 (12)
N1—C3—C4—C21	−171.01 (11)	C11—C12—C13—C14	−1.4 (2)
C25—C3—C4—C21	7.82 (19)	C10—C9—C14—C13	0.80 (19)
N1—C3—C4—C5	10.87 (17)	C7—C9—C14—C13	−179.78 (12)
C25—C3—C4—C5	−170.29 (11)	C12—C13—C14—C9	0.5 (2)
C2—C1—C5—C6	−89.71 (13)	C8—N2—C15—C16	−148.56 (12)
C23—C1—C5—C6	83.08 (12)	N3—N2—C15—C16	22.74 (17)
C2—C1—C5—C4	31.85 (15)	C8—N2—C15—C20	28.37 (18)
C23—C1—C5—C4	−155.36 (10)	N3—N2—C15—C20	−160.34 (11)
C3—C4—C5—C6	88.64 (13)	C20—C15—C16—C17	0.22 (19)
C21—C4—C5—C6	−89.49 (12)	N2—C15—C16—C17	177.11 (12)
C3—C4—C5—C1	−32.51 (14)	C15—C16—C17—C18	−0.8 (2)
C21—C4—C5—C1	149.37 (11)	C16—C17—C18—C19	0.7 (2)
C1—C5—C6—C8	39.26 (15)	C17—C18—C19—C20	0.0 (2)
C4—C5—C6—C8	−81.93 (14)	C18—C19—C20—C15	−0.63 (19)
C1—C5—C6—C7	−144.34 (12)	C16—C15—C20—C19	0.50 (18)
C4—C5—C6—C7	94.47 (14)	N2—C15—C20—C19	−176.42 (11)
N2—N3—C7—C6	0.19 (13)	C22—O4—C21—O3	2.43 (18)
N2—N3—C7—C9	−178.72 (10)	C22—O4—C21—C4	−176.47 (12)
C8—C6—C7—N3	0.11 (14)	C3—C4—C21—O3	−3.0 (2)
C5—C6—C7—N3	−176.84 (11)	C5—C4—C21—O3	175.14 (12)
C8—C6—C7—C9	178.90 (12)	C3—C4—C21—O4	175.88 (11)
C5—C6—C7—C9	1.9 (2)	C5—C4—C21—O4	−6.03 (15)
N3—N2—C8—C6	0.53 (14)	C24—O2—C23—O1	−3.27 (17)
C15—N2—C8—C6	172.54 (11)	C24—O2—C23—C1	176.54 (10)
C7—C6—C8—N2	−0.38 (13)	C2—C1—C23—O1	−18.1 (2)
C5—C6—C8—N2	176.81 (11)	C5—C1—C23—O1	169.29 (12)
N3—C7—C9—C14	50.18 (17)	C2—C1—C23—O2	162.14 (11)
C6—C7—C9—C14	−128.52 (14)	C5—C1—C23—O2	−10.52 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the pyrazole (N2/N3/C6–C8) and benzene (C15–C20) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2W	0.904 (18)	2.001 (18)	2.9020 (14)	175.2 (15)
O1W—H2W1···N3	0.90 (2)	2.05 (2)	2.9449 (14)	174 (2)
O2W—H2W2···O1Wⁱ	0.98 (3)	1.84 (3)	2.7986 (15)	166 (2)
O2W—H1W2···O3ⁱⁱ	0.90 (3)	1.91 (3)	2.8074 (14)	174 (2)
O1W—H1W1···O2Wⁱⁱⁱ	0.87 (3)	2.06 (3)	2.9274 (15)	178 (2)
C20—H20A···O1W^iv	0.95	2.44	3.2980 (16)	151
C13—H13A···Cg2^v	0.95	2.90	3.6957 (14)	142
C18—H18A···Cg1^vi	0.95	2.63	3.3682 (15)	135
C25—H25A···Cg2ⁱ	0.98	2.87	3.7231 (14)	146
C27—H27C···Cg1^v	0.98	2.62	3.5720 (17)	164

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇N₃O₅·2H₂O
M_r	509.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.1279 (9), 11.6313 (7), 15.3780 (9)
β (°)	93.358 (1)
V (Å³)	2522.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.17 × 0.14

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	28375, 7347, 5683
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.131, 1.04
No. of reflections	7347
No. of parameters	359
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.24

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the pyrazole (N2/N3/C6–C8) and benzene (C15–C20) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2W	0.904 (18)	2.001 (18)	2.9020 (14)	175.2 (15)
O1W—H2W1···N3	0.90 (2)	2.05 (2)	2.9449 (14)	174 (2)
O2W—H2W2···O1Wⁱ	0.98 (3)	1.84 (3)	2.7986 (15)	166 (2)
O2W—H1W2···O3ⁱⁱ	0.90 (3)	1.91 (3)	2.8074 (14)	174 (2)
O1W—H1W1···O2Wⁱⁱⁱ	0.87 (3)	2.06 (3)	2.9274 (15)	178 (2)
C20—H20A···O1W^iv	0.95	2.44	3.2980 (16)	150.9
C13—H13A···Cg2^v	0.9500	2.90	3.6957 (14)	142
C18—H18A···Cg1^vi	0.9500	2.63	3.3682 (15)	135
C25—H25A···Cg2ⁱ	0.9800	2.87	3.7231 (14)	146
C27—H27C···Cg1^v	0.9800	2.62	3.5720 (17)	164

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. AMI is thankful to the Board of Research in Nuclear Sciences, Government of India, for a Young Scientist award. AMI also thanks the Vision Group on Science & Technology, Government of Karnataka, India, for the best research paper award.

References

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Volume 68| Part 7| July 2012| Pages o2210-o2211

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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