Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Fun, H.-K.; Yeap, C.S.; Sujith, K.V.; Kalluraya, B.

doi:10.1107/S1600536809016365

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1229

doi:10.1107/S1600536809016365

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Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § K. V. Sujith ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 April 2009; accepted 30 April 2009; online 7 May 2009)

In the title compound, C₁₈H₁₉ClN₄O₃, the dihydropyrimidinone ring adopts a flattened boat conformation. The dihedral angle between the phenyl and pyrazole rings is 43.39 (6)°. An intramolecular C—H⋯O contact generates an S(8) ring motif that stabilizes the molecular conformation and precludes the carbonyl O atom of the ester group from forming intermolecular interactions. Molecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds and the dimers are linked into infinite chains along [101] by N—H⋯N hydrogen bonds.

Related literature

For medicinal applications of pyrimidinone derivatives, see: Atwal (1990 ); Desai et al. (2006 ); Wipf & Cunningham (1995 ); Bedia et al. (2006 ). For a related structure, see: Fun et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₉ClN₄O₃
M_r = 374.82
Triclinic, $[P \overline 1]$
a = 7.9083 (2) Å
b = 10.2600 (2) Å
c = 10.9075 (3) Å
α = 93.394 (1)°
β = 99.379 (1)°
γ = 90.203 (1)°
V = 871.58 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 110 K
0.56 × 0.26 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.875, T_max = 0.950
18224 measured reflections
5048 independent reflections
4355 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.05
5048 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2ⁱ	0.863 (16)	2.233 (16)	3.0601 (14)	160.7 (14)
N4—H1N4⋯O1ⁱⁱ	0.882 (17)	1.960 (17)	2.8418 (13)	176.8 (17)
C18—H18C⋯O3	0.96	2.59	3.2850 (15)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809016365/tk2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016365/tk2442Isup2.hkl

checkCIF report

Comment top

Pyrimidinones have drawn widespread attention due to their medicinal applications (Atwal, 1990). A variety of dihydropyrimidinone derivatives have been screened for anti-hypertension (Desai et al., 2006), anti-bacterial and anti-carcinogenic (Wipf & Cunningham, 1995), and anti-tuberculosis activity (Bedia et al., 2006). Prompted by these observations and in continuation of our work in this area, herein we report the crystal structure of the title compound, (I).

In (I), Fig. 1, the dihydropyrimidinone ring adopts a flattened boat conformation. The dihedral angle between the phenyl ring and the pyrazole ring is 43.39 (6)°. Bond lengths and angles are within normal ranges and comparable to a related structure (Fun et al., 2009). An intramolecular C18—H18C···O3 contact generates a S(8) ring motif (Bernstein et al., 1995) which stabilises the molecular conformation and precludes the O3 atom from forming intermolecular contacts. The molecules are linked into centrosymmetric dimers by N—H···O hydrogen bonds (Table 1). The dimers are further linked into infinite chains along [101] by N—H···N hydrogen bonds (Fig. 2).

Related literature top

For medicinal applications of pyrimidinone derivatives, see: Atwal (1990); Desai et al. (2006); Wipf & Cunningham (1995); Bedia et al. (2006). For a related structure, see: Fun et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

For related literature, see: Allen et al. (1987).

Experimental top

Compound (I) was obtained by refluxing a mixture of 1-phenyl-3-methyl-5-chloropyrazole-4-aldehyde (0.01 mol), ethyl acetoacetate (0.015 mol) and urea (0.01 mol) in ethanol (25 ml). The excess alcohol was removed under reduced pressure. After cooling the reaction mixture to room temperature, the contents were poured into ice-cold water (100 ml). The solid mass separated was collected by filtration and dried. Crystals were obtained from ethanol by slow evaporation (Yield 59%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (I) with atom labels and 50% probability ellipsoids for non-H atoms. An intramolecular C—H···O contact is shown as dashed lines.
	Fig. 2. A view of the crystal packing in (I), showing an infinite chain along the [101] direction. Intermolecular hydrogen bonds are shown as dashed lines.

Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo- 1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₈H₁₉ClN₄O₃	Z = 2
M_r = 374.82	F(000) = 392
Triclinic, P1	D_x = 1.428 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9083 (2) Å	Cell parameters from 9944 reflections
b = 10.2600 (2) Å	θ = 2.6–35.8°
c = 10.9075 (3) Å	µ = 0.25 mm⁻¹
α = 93.394 (1)°	T = 110 K
β = 99.379 (1)°	Block, colourless
γ = 90.203 (1)°	0.56 × 0.26 × 0.21 mm
V = 871.58 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5048 independent reflections
Radiation source: fine-focus sealed tube	4355 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.875, T_max = 0.950	k = −14→14
18224 measured reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0515P)² + 0.3283P] where P = (F_o² + 2F_c²)/3
5048 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₉ClN₄O₃	γ = 90.203 (1)°
M_r = 374.82	V = 871.58 (4) Å³
Triclinic, P1	Z = 2
a = 7.9083 (2) Å	Mo Kα radiation
b = 10.2600 (2) Å	µ = 0.25 mm⁻¹
c = 10.9075 (3) Å	T = 110 K
α = 93.394 (1)°	0.56 × 0.26 × 0.21 mm
β = 99.379 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5048 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4355 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.950	R_int = 0.026
18224 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
5048 reflections	Δρ_min = −0.30 e Å⁻³
257 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 110.0 (1) K.

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
Cl1	0.16502 (4)	0.27288 (3)	0.28593 (3)	0.01867 (8)
O1	0.09492 (11)	0.60474 (9)	0.13406 (8)	0.01980 (18)
O2	0.64558 (11)	0.20298 (9)	0.00629 (8)	0.02096 (19)
O3	0.77714 (11)	0.29869 (9)	0.18745 (8)	0.02079 (19)
N1	0.40982 (13)	0.25693 (10)	0.48878 (9)	0.01486 (19)
N2	0.57439 (13)	0.29637 (10)	0.53670 (9)	0.01546 (19)
N3	0.36526 (13)	0.54573 (10)	0.21278 (9)	0.01470 (19)
N4	0.21476 (13)	0.43462 (10)	0.03761 (9)	0.0162 (2)
C1	0.41198 (18)	0.06888 (12)	0.61334 (11)	0.0202 (2)
H1A	0.5286	0.0600	0.6116	0.024*
C2	0.3256 (2)	−0.01924 (13)	0.67359 (12)	0.0253 (3)
H2A	0.3844	−0.0884	0.7115	0.030*
C3	0.1527 (2)	−0.00483 (14)	0.67768 (12)	0.0265 (3)
H3A	0.0951	−0.0654	0.7165	0.032*
C4	0.06518 (18)	0.09986 (14)	0.62404 (12)	0.0254 (3)
H4A	−0.0503	0.1106	0.6289	0.030*
C5	0.14923 (16)	0.18874 (13)	0.56301 (11)	0.0202 (2)
H5A	0.0910	0.2594	0.5276	0.024*
C6	0.32146 (16)	0.17084 (11)	0.55550 (10)	0.0161 (2)
C7	0.36219 (14)	0.30274 (11)	0.37349 (10)	0.0143 (2)
C8	0.49610 (14)	0.37464 (11)	0.34481 (10)	0.0132 (2)
C9	0.62520 (14)	0.36737 (11)	0.45051 (10)	0.0144 (2)
C10	0.50187 (14)	0.44856 (11)	0.22960 (10)	0.0135 (2)
H10A	0.6117	0.4960	0.2419	0.016*
C11	0.21883 (15)	0.53209 (11)	0.13033 (10)	0.0150 (2)
C12	0.35013 (15)	0.35289 (11)	0.02438 (10)	0.0146 (2)
C13	0.49312 (14)	0.35937 (11)	0.11231 (10)	0.0140 (2)
C14	0.65113 (15)	0.28596 (11)	0.10717 (11)	0.0155 (2)
C15	0.80143 (17)	0.13146 (13)	−0.00265 (12)	0.0223 (3)
H15A	0.8243	0.0716	0.0635	0.027*
H15B	0.8983	0.1912	0.0039	0.027*
C16	0.7726 (2)	0.05757 (18)	−0.12749 (15)	0.0387 (4)
H16A	0.8746	0.0112	−0.1390	0.058*
H16B	0.7456	0.1177	−0.1918	0.058*
H16C	0.6793	−0.0034	−0.1314	0.058*
C17	0.31577 (17)	0.26349 (13)	−0.09159 (12)	0.0201 (2)
H17A	0.207 (3)	0.2792 (18)	−0.1382 (18)	0.034 (5)*
H17B	0.316 (3)	0.175 (2)	−0.0718 (18)	0.038 (5)*
H17C	0.398 (2)	0.2794 (18)	−0.1447 (17)	0.034 (5)*
C18	0.79965 (15)	0.42889 (12)	0.47221 (12)	0.0187 (2)
H18A	0.8530	0.4188	0.5566	0.028*
H18B	0.7902	0.5201	0.4575	0.028*
H18C	0.8679	0.3874	0.4164	0.028*
H1N3	0.367 (2)	0.6038 (15)	0.2734 (15)	0.016 (4)*
H1N4	0.120 (2)	0.4247 (17)	−0.0173 (17)	0.026 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01327 (13)	0.02560 (15)	0.01588 (13)	−0.00443 (10)	−0.00218 (9)	0.00376 (10)
O1	0.0153 (4)	0.0211 (4)	0.0210 (4)	0.0060 (3)	−0.0022 (3)	−0.0012 (3)
O2	0.0159 (4)	0.0277 (5)	0.0182 (4)	0.0091 (3)	0.0006 (3)	−0.0024 (3)
O3	0.0145 (4)	0.0270 (5)	0.0195 (4)	0.0048 (3)	−0.0011 (3)	0.0009 (3)
N1	0.0128 (4)	0.0176 (4)	0.0136 (4)	−0.0006 (3)	−0.0002 (3)	0.0026 (3)
N2	0.0128 (4)	0.0175 (4)	0.0149 (4)	0.0011 (3)	−0.0010 (3)	0.0006 (3)
N3	0.0139 (4)	0.0149 (4)	0.0140 (4)	0.0030 (3)	−0.0013 (3)	0.0004 (3)
N4	0.0122 (5)	0.0200 (5)	0.0149 (4)	0.0032 (4)	−0.0019 (4)	−0.0010 (4)
C1	0.0254 (6)	0.0195 (5)	0.0158 (5)	0.0032 (5)	0.0035 (4)	0.0025 (4)
C2	0.0378 (8)	0.0200 (6)	0.0182 (6)	0.0003 (5)	0.0033 (5)	0.0047 (5)
C3	0.0361 (8)	0.0271 (6)	0.0160 (6)	−0.0124 (6)	0.0031 (5)	0.0039 (5)
C4	0.0224 (6)	0.0350 (7)	0.0190 (6)	−0.0072 (5)	0.0037 (5)	0.0033 (5)
C5	0.0192 (6)	0.0236 (6)	0.0179 (5)	−0.0001 (4)	0.0027 (4)	0.0033 (4)
C6	0.0201 (6)	0.0164 (5)	0.0115 (5)	−0.0015 (4)	0.0021 (4)	0.0010 (4)
C7	0.0132 (5)	0.0161 (5)	0.0129 (5)	0.0009 (4)	−0.0002 (4)	0.0014 (4)
C8	0.0110 (5)	0.0147 (5)	0.0133 (5)	0.0017 (4)	0.0004 (4)	0.0009 (4)
C9	0.0125 (5)	0.0150 (5)	0.0147 (5)	0.0022 (4)	−0.0002 (4)	−0.0004 (4)
C10	0.0100 (5)	0.0159 (5)	0.0141 (5)	0.0011 (4)	0.0000 (4)	0.0026 (4)
C11	0.0145 (5)	0.0155 (5)	0.0147 (5)	0.0006 (4)	0.0006 (4)	0.0030 (4)
C12	0.0132 (5)	0.0168 (5)	0.0139 (5)	0.0017 (4)	0.0023 (4)	0.0020 (4)
C13	0.0125 (5)	0.0164 (5)	0.0132 (5)	0.0019 (4)	0.0017 (4)	0.0021 (4)
C14	0.0142 (5)	0.0180 (5)	0.0148 (5)	0.0018 (4)	0.0027 (4)	0.0044 (4)
C15	0.0179 (6)	0.0280 (6)	0.0212 (6)	0.0107 (5)	0.0032 (5)	0.0016 (5)
C16	0.0343 (8)	0.0504 (10)	0.0292 (8)	0.0220 (7)	0.0025 (6)	−0.0105 (7)
C17	0.0182 (6)	0.0246 (6)	0.0157 (5)	0.0029 (5)	−0.0008 (4)	−0.0031 (4)
C18	0.0120 (5)	0.0226 (6)	0.0200 (6)	0.0000 (4)	−0.0010 (4)	0.0007 (4)

Geometric parameters (Å, º) top

Cl1—C7	1.7070 (12)	C5—C6	1.3899 (17)
O1—C11	1.2378 (14)	C5—H5A	0.9300
O2—C14	1.3456 (14)	C7—C8	1.3760 (16)
O2—C15	1.4505 (14)	C8—C9	1.4158 (15)
O3—C14	1.2157 (14)	C8—C10	1.5125 (15)
N1—C7	1.3641 (14)	C9—C18	1.4924 (16)
N1—N2	1.3712 (13)	C10—C13	1.5202 (15)
N1—C6	1.4268 (15)	C10—H10A	0.9800
N2—C9	1.3334 (15)	C12—C13	1.3570 (15)
N3—C11	1.3468 (14)	C12—C17	1.5047 (16)
N3—C10	1.4695 (14)	C13—C14	1.4685 (15)
N3—H1N3	0.862 (16)	C15—C16	1.5020 (19)
N4—C11	1.3760 (15)	C15—H15A	0.9700
N4—C12	1.3828 (14)	C15—H15B	0.9700
N4—H1N4	0.883 (18)	C16—H16A	0.9600
C1—C2	1.3886 (18)	C16—H16B	0.9600
C1—C6	1.3932 (17)	C16—H16C	0.9600
C1—H1A	0.9300	C17—H17A	0.95 (2)
C2—C3	1.383 (2)	C17—H17B	0.95 (2)
C2—H2A	0.9300	C17—H17C	0.956 (19)
C3—C4	1.387 (2)	C18—H18A	0.9600
C3—H3A	0.9300	C18—H18B	0.9600
C4—C5	1.3887 (18)	C18—H18C	0.9600
C4—H4A	0.9300

C14—O2—C15	115.79 (9)	C8—C10—C13	112.92 (9)
C7—N1—N2	110.16 (9)	N3—C10—H10A	107.5
C7—N1—C6	130.02 (10)	C8—C10—H10A	107.5
N2—N1—C6	119.60 (9)	C13—C10—H10A	107.5
C9—N2—N1	105.46 (9)	O1—C11—N3	122.70 (10)
C11—N3—C10	125.12 (9)	O1—C11—N4	120.82 (10)
C11—N3—H1N3	117.1 (10)	N3—C11—N4	116.45 (10)
C10—N3—H1N3	115.4 (10)	C13—C12—N4	119.61 (10)
C11—N4—C12	124.24 (10)	C13—C12—C17	127.57 (10)
C11—N4—H1N4	117.5 (11)	N4—C12—C17	112.82 (10)
C12—N4—H1N4	118.3 (11)	C12—C13—C14	125.95 (10)
C2—C1—C6	119.05 (12)	C12—C13—C10	120.88 (10)
C2—C1—H1A	120.5	C14—C13—C10	113.16 (9)
C6—C1—H1A	120.5	O3—C14—O2	122.46 (11)
C3—C2—C1	120.45 (12)	O3—C14—C13	122.92 (11)
C3—C2—H2A	119.8	O2—C14—C13	114.63 (10)
C1—C2—H2A	119.8	O2—C15—C16	106.46 (10)
C2—C3—C4	120.08 (13)	O2—C15—H15A	110.4
C2—C3—H3A	120.0	C16—C15—H15A	110.4
C4—C3—H3A	120.0	O2—C15—H15B	110.4
C3—C4—C5	120.28 (13)	C16—C15—H15B	110.4
C3—C4—H4A	119.9	H15A—C15—H15B	108.6
C5—C4—H4A	119.9	C15—C16—H16A	109.5
C4—C5—C6	119.22 (12)	C15—C16—H16B	109.5
C4—C5—H5A	120.4	H16A—C16—H16B	109.5
C6—C5—H5A	120.4	C15—C16—H16C	109.5
C5—C6—C1	120.82 (12)	H16A—C16—H16C	109.5
C5—C6—N1	120.71 (11)	H16B—C16—H16C	109.5
C1—C6—N1	118.47 (11)	C12—C17—H17A	111.0 (11)
N1—C7—C8	108.70 (10)	C12—C17—H17B	111.1 (12)
N1—C7—Cl1	123.11 (9)	H17A—C17—H17B	106.9 (16)
C8—C7—Cl1	128.18 (9)	C12—C17—H17C	110.3 (11)
C7—C8—C9	103.79 (10)	H17A—C17—H17C	106.4 (16)
C7—C8—C10	128.17 (10)	H17B—C17—H17C	111.0 (17)
C9—C8—C10	128.00 (10)	C9—C18—H18A	109.5
N2—C9—C8	111.88 (10)	C9—C18—H18B	109.5
N2—C9—C18	120.43 (10)	H18A—C18—H18B	109.5
C8—C9—C18	127.69 (11)	C9—C18—H18C	109.5
N3—C10—C8	111.17 (9)	H18A—C18—H18C	109.5
N3—C10—C13	110.10 (9)	H18B—C18—H18C	109.5

C7—N1—N2—C9	0.68 (12)	C11—N3—C10—C8	−103.04 (12)
C6—N1—N2—C9	175.80 (10)	C11—N3—C10—C13	22.87 (15)
C6—C1—C2—C3	−0.95 (19)	C7—C8—C10—N3	57.33 (15)
C1—C2—C3—C4	−1.6 (2)	C9—C8—C10—N3	−120.05 (12)
C2—C3—C4—C5	1.8 (2)	C7—C8—C10—C13	−67.00 (15)
C3—C4—C5—C6	0.54 (19)	C9—C8—C10—C13	115.62 (12)
C4—C5—C6—C1	−3.09 (18)	C10—N3—C11—O1	166.80 (11)
C4—C5—C6—N1	177.20 (11)	C10—N3—C11—N4	−15.22 (16)
C2—C1—C6—C5	3.29 (18)	C12—N4—C11—O1	177.43 (11)
C2—C1—C6—N1	−176.99 (11)	C12—N4—C11—N3	−0.59 (17)
C7—N1—C6—C5	−46.54 (17)	C11—N4—C12—C13	5.61 (18)
N2—N1—C6—C5	139.45 (11)	C11—N4—C12—C17	−174.82 (11)
C7—N1—C6—C1	133.75 (13)	N4—C12—C13—C14	−175.52 (11)
N2—N1—C6—C1	−40.27 (15)	C17—C12—C13—C14	5.0 (2)
N2—N1—C7—C8	−0.59 (13)	N4—C12—C13—C10	4.26 (17)
C6—N1—C7—C8	−175.05 (11)	C17—C12—C13—C10	−175.23 (11)
N2—N1—C7—Cl1	−179.88 (8)	N3—C10—C13—C12	−16.61 (15)
C6—N1—C7—Cl1	5.67 (17)	C8—C10—C13—C12	108.30 (12)
N1—C7—C8—C9	0.25 (12)	N3—C10—C13—C14	163.20 (9)
Cl1—C7—C8—C9	179.49 (9)	C8—C10—C13—C14	−71.89 (12)
N1—C7—C8—C10	−177.62 (10)	C15—O2—C14—O3	−1.48 (17)
Cl1—C7—C8—C10	1.62 (18)	C15—O2—C14—C13	178.58 (10)
N1—N2—C9—C8	−0.52 (12)	C12—C13—C14—O3	177.86 (12)
N1—N2—C9—C18	178.99 (10)	C10—C13—C14—O3	−1.93 (17)
C7—C8—C9—N2	0.18 (13)	C12—C13—C14—O2	−2.20 (17)
C10—C8—C9—N2	178.06 (10)	C10—C13—C14—O2	178.00 (10)
C7—C8—C9—C18	−179.29 (11)	C14—O2—C15—C16	−173.84 (12)
C10—C8—C9—C18	−1.41 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2ⁱ	0.863 (16)	2.233 (16)	3.0601 (14)	160.7 (14)
N4—H1N4···O1ⁱⁱ	0.882 (17)	1.960 (17)	2.8418 (13)	176.8 (17)
C18—H18C···O3	0.96	2.59	3.2850 (15)	129

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉ClN₄O₃
M_r	374.82
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	7.9083 (2), 10.2600 (2), 10.9075 (3)
α, β, γ (°)	93.394 (1), 99.379 (1), 90.203 (1)
V (Å³)	871.58 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.56 × 0.26 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.875, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	18224, 5048, 4355
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.05
No. of reflections	5048
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N3—H1N3···N2ⁱ	0.863 (16)	2.233 (16)	3.0601 (14)	160.7 (14)
N4—H1N4···O1ⁱⁱ	0.882 (17)	1.960 (17)	2.8418 (13)	176.8 (17)
C18—H18C···O3	0.96	2.59	3.2850 (15)	129

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose (grant No. 1001/PFIZIK/811012). CSY thanks the Malaysian government and Universiti Sains Malaysia for the award of the post of Research Officer under Science Fund (grant No. 305/PFIZIK/613312).

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. CrossRef Web of Science Google Scholar
Atwal, K. S. (1990). J. Med. Chem. 33, 1510–1518. CSD CrossRef CAS PubMed Web of Science Google Scholar
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Bruker (2005). 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
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Fun, H.-K., Yeap, C. S., Babu, M. & Kalluraya, B. (2009). Acta Cryst. E65, o1188–o1189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate