Crystal structure of ethyl 6-(chloro­meth­yl)-4-(4-chloro­phen­yl)-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Bharanidharan, S.; Saleem, H.; Gunasekaran, B.; Padusha, M.S.A.; Suresh, M.

doi:10.1107/S1600536814023046

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1185-o1186

doi:10.1107/S1600536814023046

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Crystal structure of ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

S. Bharanidharan,^a H. Saleem,^a B. Gunasekaran,^b ^* M. Syed Ali Padusha ^c and M. Suresh ^d

^aDepartment of Physics, Annamalai University, Annamalainagar 608 002, Tamil Nadu, India, ^bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram District, Chennai 603 203, Tamil Nadu, India, ^cPG and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu 620 020, India, and ^dPG and Research Dept of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu 620 020, India
^*Correspondence e-mail: phdguna@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 16 October 2014; accepted 20 October 2014; online 24 October 2014)

In the title compound, C₁₄H₁₄Cl₂N₂O₃, the chlorophenyl ring makes a dihedral angle of 87.08 (9)° with the tetrahydropyrimidine ring. There is a short intramolecular C—H⋯O contact present. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R²₂(8) ring motif. The dimers are linked via a second pair of N—H⋯O hydrogen bonds, this time enclosing an R⁴₄(20) ring motif, forming ribbons along [100]. The ribbons are linked via C—H⋯O hydrogen bonds, forming sheets lying parallel to (001). The terminal ethyl group is disordered over two positions with an occupancy ratio of 0.654 (17):0.346 (17).

Keywords: crystal structure; tetrahydropyrimidine; inversion dimers; anticarcinogenic; antihypertensive; calcium channel modulators..

CCDC reference: 1030125

1. Related literature

For the many biological activities of dihydropyrimidinone derivatives, see: Atwal et al. (1991 ); Jauk et al. (2000 ); Kato (1984 ); Wipf & Cunningham (1995 ); Bedia et al. (2006 ); For related structures, see: Nayak et al. (2009 ); Yuvaraj et al. (2010 );

2. Experimental

2.1. Crystal data

C₁₄H₁₄Cl₂N₂O₃
M_r = 329.17
Triclinic, $[P \overline 1]$
a = 7.4698 (3) Å
b = 9.1436 (3) Å
c = 12.6085 (4) Å
α = 107.147 (2)°
β = 99.941 (2)°
γ = 105.331 (2)°
V = 763.71 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 $[Sheldrick, G. M. (1996). SADABS, University of G\"ottingen, Germany.]$ ) T_min = 0.897, T_max = 0.917
20157 measured reflections
3945 independent reflections
2911 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.153
S = 1.03
3945 reflections
211 parameters
26 restraints
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.04	2.885 (2)	166
N1—H1⋯O2ⁱⁱ	0.86	2.23	3.070 (2)	166
C11—H11B⋯O1ⁱⁱⁱ	0.97	2.50	3.069 (3)	117
C11—H11A⋯O2	0.97	2.14	2.814 (3)	126
Symmetry codes: (i) -x+1, -y-1, -z; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

CCDC reference: 1030125

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814023046/su5005sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023046/su5005Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023046/su5005Isup3.cml

checkCIF report

Comment top

Dihydropyrimidinones (DHPM) and their derivatives are important on account of their wide range of applications in therapeutic and pharmacology, namely because of their anticarcinogenic (Kato, 1984), antihypertensive (Atwal et al., 1991) and calcium channel modulators (Jauk et al., 2000) activities. These derivatives have also been screened for anti-bacterial (Wipf & Cunningham, 1995), and anti-tuberculosis activity (Bedia et al., 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with those reported fro similar structures (Nayak et al., 2009; Yuvaraj et al., 2010). The chlorophenyl ring makes a dihedral angles of 87.08 (9) ° with the tetrahydropyrimidine ring. There is a short intramolecular C—H···O contact (Table 1).

In the crystal, molecules are linked via a pair of N—H···O hydrogen bonds forming inversion dimers with an R²₂(8) ring motif. The dimers are linked via a second pair of N—H···O hydrogen bonds, this time enclosing an R⁴₄(20) ring motif, forming ribbons along [100]. The ribbons are linked via C—H···O hydrogen bonds forming sheets lying parallel to (001); see Table 1 and Fig. 2 for details.

Related literature top

For the many biological activities of dihydropyrimidinone derivatives, see: Atwal et al. (1991); Jauk et al. (2000); Kato (1984); Wipf & Cunningham (1995); Bedia et al. (2006); For related structures, see: Nayak et al. (2009); Yuvaraj et al. (2010);

Experimental top

A mixture of ethyl-4-chloro acetoacetate (4.1 ml, 0.025 mol), 4-chlorobenzaldehyde (3.6 g, 0.025 mol), and urea (4.5 g, 0.075 mol) in ethanol (5 ml) was heated under reflux in the presence of concentrated HCl (1 mL) for 5 h (monitored by TLC). The reaction mixture, after being cooled to room temperature, was poured onto crushed ice and stirred for 5–10 min. The solid was separated and filtered under suction, washed with ice-cold water (50 ml), and then recrystallized from hot ethanol to afford pure product [m.p. 437 K; yield 76%].

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₄H₁₄Cl₂N₂O₃	Z = 2
M_r = 329.17	F(000) = 340
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4698 (3) Å	Cell parameters from 4865 reflections
b = 9.1436 (3) Å	θ = 2.5–30.1°
c = 12.6085 (4) Å	µ = 0.44 mm⁻¹
α = 107.147 (2)°	T = 295 K
β = 99.941 (2)°	Block, colourless
γ = 105.331 (2)°	0.30 × 0.25 × 0.20 mm
V = 763.71 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	3945 independent reflections
Radiation source: fine-focus sealed tube	2911 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 0 pixels mm^-1	θ_max = 31.0°, θ_min = 2.5°
ω and ϕ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.897, T_max = 0.917	l = −18→17
20157 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0628P)² + 0.6453P] where P = (F_o² + 2F_c²)/3
3945 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.64 e Å⁻³
26 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₄H₁₄Cl₂N₂O₃	γ = 105.331 (2)°
M_r = 329.17	V = 763.71 (5) Å³
Triclinic, P1	Z = 2
a = 7.4698 (3) Å	Mo Kα radiation
b = 9.1436 (3) Å	µ = 0.44 mm⁻¹
c = 12.6085 (4) Å	T = 295 K
α = 107.147 (2)°	0.30 × 0.25 × 0.20 mm
β = 99.941 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3945 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2911 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.917	R_int = 0.022
20157 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	26 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	Δρ_max = 0.64 e Å⁻³
3945 reflections	Δρ_min = −0.53 e Å⁻³
211 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.8422 (5)	0.1384 (4)	0.5387 (2)	0.0651 (8)
C2	0.7145 (5)	−0.0099 (4)	0.4712 (3)	0.0725 (9)
H2	0.6712	−0.0878	0.5031	0.087*
C3	0.6488 (4)	−0.0442 (3)	0.3538 (2)	0.0598 (7)
H3	0.5588	−0.1453	0.3073	0.072*
C4	0.7137 (3)	0.0674 (3)	0.30506 (18)	0.0361 (4)
C5	0.8424 (5)	0.2165 (4)	0.3761 (3)	0.0699 (9)
H5	0.8876	0.2950	0.3452	0.084*
C6	0.9060 (6)	0.2518 (4)	0.4938 (3)	0.0895 (12)
H6	0.9925	0.3537	0.5414	0.107*
C7	0.6508 (3)	0.0279 (2)	0.17587 (17)	0.0306 (4)
H7	0.7032	0.1280	0.1613	0.037*
C8	0.6382 (3)	−0.2509 (2)	0.06968 (18)	0.0342 (4)
C9	0.3408 (3)	−0.1913 (2)	0.06544 (17)	0.0315 (4)
C10	0.4341 (3)	−0.0329 (2)	0.12644 (16)	0.0300 (4)
C11	0.1275 (3)	−0.2650 (3)	0.0111 (2)	0.0454 (5)
H11A	0.0752	−0.1799	0.0068	0.055*
H11B	0.0673	−0.3162	0.0593	0.055*
C12	0.3328 (3)	0.0848 (3)	0.15276 (18)	0.0360 (4)
N1	0.7306 (2)	−0.0910 (2)	0.11509 (15)	0.0338 (4)
H1	0.8450	−0.0555	0.1081	0.041*
N2	0.4415 (2)	−0.2989 (2)	0.05067 (17)	0.0375 (4)
H2A	0.3781	−0.4009	0.0285	0.045*
O1	0.7187 (2)	−0.35121 (19)	0.04214 (16)	0.0488 (4)
O2	0.1610 (2)	0.0561 (2)	0.13615 (16)	0.0508 (4)
O3	0.4586 (2)	0.23490 (19)	0.20251 (17)	0.0554 (5)
C13	0.374 (3)	0.3618 (16)	0.2478 (12)	0.086 (4)	0.654 (17)
H13A	0.2924	0.3745	0.1847	0.103*	0.654 (17)
H13B	0.2959	0.3318	0.2971	0.103*	0.654 (17)
C14	0.5303 (12)	0.5098 (7)	0.3121 (11)	0.116 (4)	0.654 (17)
H14A	0.6081	0.4964	0.3752	0.174*	0.654 (17)
H14B	0.4803	0.5955	0.3415	0.174*	0.654 (17)
H14C	0.6076	0.5371	0.2627	0.174*	0.654 (17)
C13A	0.394 (4)	0.368 (3)	0.2319 (11)	0.070 (7)	0.346 (17)
H13C	0.2598	0.3357	0.1900	0.084*	0.346 (17)
H13D	0.4684	0.4531	0.2098	0.084*	0.346 (17)
C14A	0.414 (4)	0.428 (3)	0.3506 (12)	0.127 (10)	0.346 (17)
H14D	0.3199	0.3533	0.3697	0.190*	0.346 (17)
H14E	0.3937	0.5314	0.3713	0.190*	0.346 (17)
H14F	0.5409	0.4415	0.3920	0.190*	0.346 (17)
Cl1	0.92366 (19)	0.18204 (17)	0.68608 (7)	0.1114 (4)
Cl2	0.07043 (8)	−0.41074 (8)	−0.12863 (5)	0.0522 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0719 (18)	0.085 (2)	0.0334 (12)	0.0407 (17)	0.0004 (12)	0.0089 (13)
C2	0.095 (2)	0.079 (2)	0.0475 (16)	0.0299 (19)	0.0186 (15)	0.0296 (15)
C3	0.0751 (18)	0.0529 (15)	0.0402 (13)	0.0083 (13)	0.0088 (12)	0.0163 (11)
C4	0.0315 (10)	0.0396 (11)	0.0348 (10)	0.0151 (8)	0.0040 (8)	0.0098 (8)
C5	0.076 (2)	0.0498 (15)	0.0523 (16)	−0.0029 (14)	−0.0110 (14)	0.0120 (12)
C6	0.099 (3)	0.069 (2)	0.0506 (18)	0.0008 (19)	−0.0216 (17)	−0.0003 (16)
C7	0.0246 (9)	0.0292 (9)	0.0363 (10)	0.0085 (7)	0.0058 (7)	0.0110 (8)
C8	0.0261 (9)	0.0363 (10)	0.0398 (10)	0.0112 (8)	0.0095 (8)	0.0122 (8)
C9	0.0228 (8)	0.0364 (10)	0.0361 (10)	0.0107 (7)	0.0095 (7)	0.0124 (8)
C10	0.0255 (9)	0.0331 (9)	0.0325 (9)	0.0112 (7)	0.0066 (7)	0.0126 (8)
C11	0.0262 (10)	0.0453 (12)	0.0516 (13)	0.0079 (9)	0.0099 (9)	0.0027 (10)
C12	0.0343 (10)	0.0374 (10)	0.0370 (10)	0.0163 (8)	0.0061 (8)	0.0123 (8)
N1	0.0207 (7)	0.0351 (9)	0.0416 (9)	0.0079 (6)	0.0086 (6)	0.0094 (7)
N2	0.0237 (8)	0.0284 (8)	0.0552 (11)	0.0069 (6)	0.0101 (7)	0.0096 (7)
O1	0.0303 (8)	0.0385 (8)	0.0734 (12)	0.0151 (6)	0.0150 (7)	0.0103 (8)
O2	0.0333 (8)	0.0521 (10)	0.0681 (11)	0.0229 (7)	0.0135 (7)	0.0155 (8)
O3	0.0431 (9)	0.0336 (8)	0.0738 (12)	0.0180 (7)	−0.0026 (8)	0.0034 (8)
C13	0.071 (6)	0.051 (6)	0.116 (9)	0.039 (4)	0.008 (6)	−0.001 (5)
C14	0.100 (5)	0.041 (3)	0.171 (9)	0.017 (3)	0.030 (5)	−0.003 (4)
C13A	0.077 (14)	0.052 (10)	0.063 (8)	0.048 (10)	−0.016 (7)	−0.009 (7)
C14A	0.18 (2)	0.138 (18)	0.075 (9)	0.115 (18)	0.028 (9)	0.000 (9)
Cl1	0.1383 (10)	0.1531 (11)	0.0355 (4)	0.0742 (8)	0.0001 (5)	0.0144 (5)
Cl2	0.0426 (3)	0.0510 (4)	0.0510 (3)	0.0153 (3)	−0.0023 (2)	0.0100 (3)

Geometric parameters (Å, º) top

C1—C6	1.342 (5)	C11—Cl2	1.766 (2)
C1—C2	1.352 (5)	C11—H11A	0.9700
C1—Cl1	1.739 (3)	C11—H11B	0.9700
C2—C3	1.388 (4)	C12—O2	1.207 (3)
C2—H2	0.9300	C12—O3	1.330 (3)
C3—C4	1.366 (3)	N1—H1	0.8600
C3—H3	0.9300	N2—H2A	0.8600
C4—C5	1.369 (3)	O3—C13A	1.4000 (10)
C4—C7	1.518 (3)	O3—C13	1.482 (8)
C5—C6	1.387 (4)	C13—C14	1.430 (19)
C5—H5	0.9300	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C7—N1	1.461 (2)	C14—H14A	0.9600
C7—C10	1.513 (2)	C14—H14B	0.9600
C7—H7	0.9800	C14—H14C	0.9600
C8—O1	1.225 (2)	C13A—C14A	1.4000 (10)
C8—N1	1.333 (3)	C13A—H13C	0.9700
C8—N2	1.373 (2)	C13A—H13D	0.9700
C9—C10	1.341 (3)	C14A—H14D	0.9600
C9—N2	1.379 (2)	C14A—H14E	0.9600
C9—C11	1.498 (3)	C14A—H14F	0.9600
C10—C12	1.466 (3)

C6—C1—C2	121.0 (3)	Cl2—C11—H11A	109.2
C6—C1—Cl1	119.8 (3)	C9—C11—H11B	109.2
C2—C1—Cl1	119.2 (3)	Cl2—C11—H11B	109.2
C1—C2—C3	119.1 (3)	H11A—C11—H11B	107.9
C1—C2—H2	120.5	O2—C12—O3	122.43 (19)
C3—C2—H2	120.5	O2—C12—C10	127.3 (2)
C4—C3—C2	121.3 (3)	O3—C12—C10	110.28 (17)
C4—C3—H3	119.4	C8—N1—C7	124.46 (16)
C2—C3—H3	119.4	C8—N1—H1	117.8
C3—C4—C5	118.0 (2)	C7—N1—H1	117.8
C3—C4—C7	121.6 (2)	C8—N2—C9	123.10 (17)
C5—C4—C7	120.4 (2)	C8—N2—H2A	118.5
C4—C5—C6	120.8 (3)	C9—N2—H2A	118.4
C4—C5—H5	119.6	C12—O3—C13A	120.4 (14)
C6—C5—H5	119.6	C12—O3—C13	114.8 (8)
C1—C6—C5	119.8 (3)	C13A—O3—C13	10.8 (18)
C1—C6—H6	120.1	C14—C13—O3	107.3 (12)
C5—C6—H6	120.1	C14—C13—H13A	110.3
N1—C7—C10	109.45 (15)	O3—C13—H13A	110.3
N1—C7—C4	110.73 (15)	C14—C13—H13B	110.3
C10—C7—C4	113.47 (16)	O3—C13—H13B	110.3
N1—C7—H7	107.7	H13A—C13—H13B	108.5
C10—C7—H7	107.7	O3—C13A—C14A	110.7 (9)
C4—C7—H7	107.7	O3—C13A—H13C	109.5
O1—C8—N1	123.56 (18)	C14A—C13A—H13C	109.5
O1—C8—N2	120.66 (19)	O3—C13A—H13D	109.5
N1—C8—N2	115.73 (17)	C14A—C13A—H13D	109.5
C10—C9—N2	120.01 (17)	H13C—C13A—H13D	108.1
C10—C9—C11	124.57 (18)	C13A—C14A—H14D	109.5
N2—C9—C11	115.41 (18)	C13A—C14A—H14E	109.5
C9—C10—C12	122.35 (17)	H14D—C14A—H14E	109.5
C9—C10—C7	119.80 (17)	C13A—C14A—H14F	109.5
C12—C10—C7	117.78 (17)	H14D—C14A—H14F	109.5
C9—C11—Cl2	112.02 (15)	H14E—C14A—H14F	109.5
C9—C11—H11A	109.2

C6—C1—C2—C3	−0.1 (5)	C10—C9—C11—Cl2	138.10 (19)
Cl1—C1—C2—C3	179.6 (3)	N2—C9—C11—Cl2	−42.8 (3)
C1—C2—C3—C4	1.4 (5)	C9—C10—C12—O2	8.7 (4)
C2—C3—C4—C5	−1.7 (5)	C7—C10—C12—O2	−168.2 (2)
C2—C3—C4—C7	176.7 (3)	C9—C10—C12—O3	−173.0 (2)
C3—C4—C5—C6	0.7 (5)	C7—C10—C12—O3	10.1 (3)
C7—C4—C5—C6	−177.7 (3)	O1—C8—N1—C7	−163.2 (2)
C2—C1—C6—C5	−0.8 (6)	N2—C8—N1—C7	19.2 (3)
Cl1—C1—C6—C5	179.4 (3)	C10—C7—N1—C8	−31.1 (3)
C4—C5—C6—C1	0.5 (6)	C4—C7—N1—C8	94.8 (2)
C3—C4—C7—N1	−68.6 (3)	O1—C8—N2—C9	−171.1 (2)
C5—C4—C7—N1	109.8 (3)	N1—C8—N2—C9	6.6 (3)
C3—C4—C7—C10	55.0 (3)	C10—C9—N2—C8	−16.8 (3)
C5—C4—C7—C10	−126.6 (3)	C11—C9—N2—C8	164.1 (2)
N2—C9—C10—C12	−174.98 (18)	O2—C12—O3—C13A	−3.8 (9)
C11—C9—C10—C12	4.0 (3)	C10—C12—O3—C13A	177.8 (9)
N2—C9—C10—C7	1.8 (3)	O2—C12—O3—C13	6.6 (7)
C11—C9—C10—C7	−179.16 (19)	C10—C12—O3—C13	−171.8 (7)
N1—C7—C10—C9	19.3 (3)	C12—O3—C13—C14	171.9 (10)
C4—C7—C10—C9	−105.0 (2)	C13A—O3—C13—C14	−65 (9)
N1—C7—C10—C12	−163.80 (17)	C12—O3—C13A—C14A	103 (2)
C4—C7—C10—C12	72.0 (2)	C13—O3—C13A—C14A	42 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.04	2.885 (2)	166
N1—H1···O2ⁱⁱ	0.86	2.23	3.070 (2)	166
C11—H11B···O1ⁱⁱⁱ	0.97	2.50	3.069 (3)	117
C11—H11A···O2	0.97	2.14	2.814 (3)	126

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.04	2.885 (2)	166
N1—H1···O2ⁱⁱ	0.86	2.23	3.070 (2)	166
C11—H11B···O1ⁱⁱⁱ	0.97	2.50	3.069 (3)	117
C11—H11A···O2	0.97	2.14	2.814 (3)	126

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

Acknowledgements

SB thanks Professor K. Ramamurthi, Department of Physics and Nanotechnology, SRM University, Chennai, for his guidance and valuable suggestions.

References

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Volume 70| Part 11| November 2014| Pages o1185-o1186

doi:10.1107/S1600536814023046

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

Crystal structure of ethyl 6-(chloro­meth­yl)-4-(4-chloro­phen­yl)-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate