2-(4-Bromo­anilino)-6-(4-chloro­phen­yl)-5-meth­oxy­carbonyl-4-methyl-3,6-dihydro­pyrimidin-1-ium chloride

Venugopala, K.N.; Nayak, S.K.; Odhav, B.

doi:10.1107/S1600536813006296

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o518-o519

doi:10.1107/S1600536813006296

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2-(4-Bromoanilino)-6-(4-chlorophenyl)-5-methoxycarbonyl-4-methyl-3,6-dihydropyrimidin-1-ium chloride

K. N. Venugopala,^a ^* Susanta K. Nayak ^b ^* and Bharti Odhav ^a

^aDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa, and ^bEquipe Chimie du Solide et Matériaux, UMR 6226 Institut des Sciences, Université de Rennes 1, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes cedex, France
^*Correspondence e-mail: katharigattav@dut.ac.za, nksusa@gmail.com

(Received 3 February 2013; accepted 5 March 2013; online 9 March 2013)

In the title molecular salt, C₁₉H₁₈BrClN₃O₂⁺·Cl⁻, the dihedral angles between the pyrimidine ring and the chlorobenzene and bromobenzene rings are 72.4 (2) and 45.5 (2)°, respectively. The dihedral angle between the chlorobenzene and bromobenzene rings is 27.5 (2)°. The conformation of the molecule is stabilized by an intramolecular C—H⋯O interaction. In the crystal, the anion and cation are linked by an N—H⋯Cl hydrogen bond. Pairs of weak C—H⋯O and C—H⋯Cl hydrogen bonds form inversion dimers. Further N—H⋯Cl hydrogen bonds form R₂¹(6) motifs and link the dimers into chains along [101]. Br⋯Cl short contacts [3.482 (2) Å] interlink the hydrogen-bonded chains along the b-axis direction.

Related literature

For a study of chloride salts of dihydropyrimidine derivatives and their anti-tubercular activity, see: Venugopala, Nayak, Pillay et al. (2012 ). For the crystal structures of dihydropyrimidine derivatives, see: Venugopala, Nayak & Odhav (2012 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₈BrClN₃O₂⁺·Cl⁻
M_r = 471.17
Monoclinic, P 2₁ /n
a = 13.2691 (15) Å
b = 11.0965 (12) Å
c = 14.9545 (17) Å
β = 114.181 (3)°
V = 2008.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.33 mm⁻¹
T = 100 K
0.08 × 0.05 × 0.03 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.835, T_max = 0.933
10242 measured reflections
3919 independent reflections
2511 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.096
S = 0.95
3919 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2	0.88	2.34	3.136 (3)	151
N2—H2⋯Cl2ⁱ	0.88	2.41	3.179 (3)	146
N3—H3⋯Cl2ⁱ	0.88	2.39	3.191 (3)	151
C5—H5A⋯O2	0.98	2.22	2.897 (5)	125
C15—H15⋯O2ⁱⁱ	0.95	2.42	3.197 (5)	139
C18—H18⋯Cl2ⁱⁱⁱ	0.95	2.81	3.702 (4)	156
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813006296/pv2621sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006296/pv2621Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006296/pv2621Isup3.cml

checkCIF report

Comment top

We have recently reported that the chloride salts of dihydropyrimidine derivatives exhibit anti-tubercular activity (Venugopala, Nayak, Pillay et al. 2012). In continuation of our work in this field and on the crystal structures of dihydropyrimidine derivatives (Venugopala, Nayak & Odhav, 2012), we now report in this article, the crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in a closely related compound (Venugopala, Nayak &Odhav, 2012).The dihedral angles between the planes of 4-chlorophenyl and 4-bromophenyl rings with the plane of the six-membered pyrimidine ring are 72.4 (2)° and 45.5 (2)°, respectively. The conformation of the title molecule is stabilized by intramolecular C5—H5···O2 interactions. The crystal structure is stabilized by the N—H···Cl hydrogen bonds and further consolidated by weak C—H···O and C—H···Cl hydrogen bonding interactions (Table 1 & Fig. 2).

In the crystal structure, Cl2 is hydrogen bonded to N2 and N3 forming six membered rings in R₂¹(6) motif (Bernstein et al.,1995). This Cl2 is also involved in a hydrogen bond (C18—H18···Cl2) with a molecule lying about an inversion center thus resulting in dimers. In addition, N1—H1···Cl2 interactions link the dimers into chains in the (1 0 1) direction. C15—H15···O2 interactions also result in macrocyclic rings about inversion centers resulting in dimers. Finally, a Br1···Cl1^* short contact (3.482 (2) Å, symmetry code ^*: x - 1/2, -y + 1/2, z + 1/2) interlinks the hydrogen bonded chains along the b axis.

Related literature top

For a study of chloride salts of dihydropyrimidine derivatives and their anti-tubercular activity, see: Venugopala, Nayak, Pillay et al. (2012). For the crystal structures of dihydropyrimidine derivatives, see: Venugopala, Nayak & Odhav (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of methyl-2-chloro-4-(4-chlorophenyl)-6-methyl-1,4- dihydropyrimidine-5-carboxylate (1 mmol) and 4-bromoaniline (1 mmol) in 2-propanol (5 mL) was refluxed for 16 h. The reaction was monitored by TLC. The reaction medium was cooled to room temperature and the product was filtered, washed with cold 2-propanol and dried to obtain the crude product. The product was purified by recrystallization using ethanol to yield 66% yield of product which was pale yellow amorphous solid (m.p. 500 (2) K). Crystals suitable for single-crystal X-ray analysis were obtained using acetone as a solvent using slow evaporation at room temperature.

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: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. A view of the title compound with the atom numbering scheme and displacement ellipsoids for non-H atoms drawn at the 50% probability level. The intramolecular interactions are shown as dashed lines.
	Fig. 2. Intermolecular N—H···Cl hydrogen-bonding interactions form infinite chains which are linked by Br···Cl short contacts along the b axis.

2-(4-Bromoanilino)-6-(4-chlorophenyl)-5-methoxycarbonyl-4-methyl-3,6-dihydropyrimidin-1-ium chloride top

Crystal data top

C₁₉H₁₈BrClN₃O₂⁺·Cl⁻	F(000) = 952
M_r = 471.17	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 500(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.2691 (15) Å	Cell parameters from 650 reflections
b = 11.0965 (12) Å	θ = 1.7–27.9°
c = 14.9545 (17) Å	µ = 2.33 mm⁻¹
β = 114.181 (3)°	T = 100 K
V = 2008.7 (4) Å³	Block, colorless
Z = 4	0.08 × 0.05 × 0.03 mm

Data collection top

Bruker Kappa DUO APEXII diffractometer	3919 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
0.5° ϕ scans and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.835, T_max = 0.933	k = −13→13
10242 measured reflections	l = −18→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0403P)²] where P = (F_o² + 2F_c²)/3
3919 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₁₈BrClN₃O₂⁺·Cl⁻	V = 2008.7 (4) Å³
M_r = 471.17	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.2691 (15) Å	µ = 2.33 mm⁻¹
b = 11.0965 (12) Å	T = 100 K
c = 14.9545 (17) Å	0.08 × 0.05 × 0.03 mm
β = 114.181 (3)°

Data collection top

Bruker Kappa DUO APEXII diffractometer	3919 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2511 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.933	R_int = 0.067
10242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 0.95	Δρ_max = 0.42 e Å⁻³
3919 reflections	Δρ_min = −0.40 e Å⁻³
246 parameters

Special details top

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
Br1	0.13690 (4)	0.30575 (4)	0.48412 (3)	0.03906 (15)
Cl1	0.62679 (9)	0.43238 (11)	0.13181 (9)	0.0497 (3)
Cl2	0.18134 (7)	0.73567 (10)	0.24229 (7)	0.0366 (3)
O1	0.4928 (2)	1.0157 (2)	0.21182 (19)	0.0336 (7)
O2	0.6208 (2)	1.1174 (3)	0.3359 (2)	0.0391 (7)
N1	0.4274 (2)	0.7807 (3)	0.3884 (2)	0.0220 (7)
H1	0.3580	0.7579	0.3678	0.026*
N2	0.5907 (2)	0.8308 (3)	0.5160 (2)	0.0244 (7)
H2	0.6422	0.8109	0.5736	0.029*
N3	0.4682 (2)	0.7087 (3)	0.5462 (2)	0.0236 (7)
H3	0.5075	0.7251	0.6085	0.028*
C1	0.4941 (4)	1.1104 (4)	0.1460 (3)	0.0420 (11)
H1A	0.5703	1.1363	0.1632	0.063*
H1B	0.4503	1.1788	0.1515	0.063*
H1C	0.4624	1.0801	0.0785	0.063*
C2	0.5598 (3)	1.0312 (3)	0.3065 (3)	0.0266 (9)
C3	0.5487 (3)	0.9312 (3)	0.3668 (3)	0.0213 (8)
C4	0.6119 (3)	0.9232 (3)	0.4638 (3)	0.0239 (9)
C5	0.7060 (3)	1.0023 (3)	0.5265 (3)	0.0320 (10)
H5A	0.6981	1.0819	0.4961	0.048*
H5B	0.7760	0.9660	0.5329	0.048*
H5C	0.7056	1.0105	0.5916	0.048*
C6	0.4680 (3)	0.8309 (3)	0.3176 (3)	0.0217 (8)
H6	0.4033	0.8674	0.2625	0.026*
C7	0.5126 (3)	0.7297 (3)	0.2746 (2)	0.0232 (8)
C8	0.6080 (3)	0.7427 (4)	0.2584 (3)	0.0282 (9)
H8	0.6504	0.8145	0.2791	0.034*
C9	0.6427 (3)	0.6536 (4)	0.2129 (3)	0.0308 (9)
H9	0.7070	0.6643	0.2008	0.037*
C10	0.5819 (3)	0.5490 (4)	0.1855 (3)	0.0308 (10)
C11	0.4875 (3)	0.5316 (4)	0.2014 (3)	0.0305 (10)
H11	0.4475	0.4581	0.1833	0.037*
C12	0.4528 (3)	0.6233 (4)	0.2441 (3)	0.0268 (9)
H12	0.3863	0.6137	0.2529	0.032*
C13	0.4936 (3)	0.7697 (3)	0.4817 (3)	0.0202 (8)
C14	0.3842 (3)	0.6193 (3)	0.5253 (3)	0.0230 (8)
C15	0.3303 (3)	0.6112 (4)	0.5866 (3)	0.0284 (9)
H15	0.3441	0.6692	0.6370	0.034*
C16	0.2553 (3)	0.5180 (4)	0.5747 (3)	0.0301 (9)
H16	0.2184	0.5112	0.6170	0.036*
C17	0.2358 (3)	0.4357 (3)	0.5001 (3)	0.0277 (9)
C18	0.2874 (3)	0.4450 (3)	0.4374 (3)	0.0246 (9)
H18	0.2711	0.3889	0.3853	0.029*
C19	0.3625 (3)	0.5356 (3)	0.4501 (3)	0.0237 (8)
H19	0.3996	0.5412	0.4078	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0491 (3)	0.0302 (2)	0.0386 (3)	−0.0145 (2)	0.0188 (2)	−0.0051 (2)
Cl1	0.0502 (7)	0.0405 (7)	0.0635 (8)	0.0083 (5)	0.0285 (6)	−0.0154 (6)
Cl2	0.0226 (5)	0.0571 (7)	0.0259 (5)	−0.0006 (5)	0.0058 (4)	0.0065 (5)
O1	0.0401 (16)	0.0293 (17)	0.0292 (16)	−0.0082 (13)	0.0117 (13)	0.0027 (12)
O2	0.0433 (17)	0.0265 (16)	0.0440 (18)	−0.0114 (14)	0.0144 (14)	−0.0019 (14)
N1	0.0136 (14)	0.0266 (19)	0.0221 (17)	−0.0004 (12)	0.0036 (13)	0.0000 (13)
N2	0.0169 (16)	0.0249 (19)	0.0239 (17)	−0.0012 (13)	0.0007 (13)	0.0002 (13)
N3	0.0243 (16)	0.0268 (19)	0.0173 (16)	−0.0040 (14)	0.0060 (13)	−0.0026 (14)
C1	0.052 (3)	0.040 (3)	0.038 (3)	−0.009 (2)	0.022 (2)	0.007 (2)
C2	0.027 (2)	0.023 (2)	0.034 (2)	−0.0016 (17)	0.0166 (19)	−0.0060 (18)
C3	0.0227 (19)	0.017 (2)	0.026 (2)	−0.0006 (15)	0.0112 (17)	−0.0029 (16)
C4	0.022 (2)	0.017 (2)	0.032 (2)	−0.0007 (15)	0.0109 (18)	−0.0044 (16)
C5	0.026 (2)	0.024 (2)	0.038 (2)	−0.0018 (17)	0.0033 (18)	−0.0081 (19)
C6	0.0198 (18)	0.023 (2)	0.0206 (19)	−0.0013 (15)	0.0063 (16)	0.0009 (15)
C7	0.026 (2)	0.023 (2)	0.0172 (19)	0.0028 (16)	0.0063 (16)	0.0027 (15)
C8	0.024 (2)	0.028 (2)	0.031 (2)	−0.0029 (17)	0.0097 (17)	−0.0013 (18)
C9	0.028 (2)	0.032 (2)	0.038 (2)	0.0020 (18)	0.0194 (19)	−0.0010 (19)
C10	0.033 (2)	0.025 (2)	0.032 (2)	0.0083 (18)	0.0110 (19)	−0.0031 (18)
C11	0.028 (2)	0.026 (2)	0.031 (2)	−0.0031 (17)	0.0042 (18)	−0.0004 (18)
C12	0.024 (2)	0.030 (2)	0.025 (2)	0.0034 (17)	0.0092 (17)	0.0019 (18)
C13	0.0185 (18)	0.019 (2)	0.025 (2)	0.0029 (15)	0.0107 (17)	−0.0035 (16)
C14	0.025 (2)	0.019 (2)	0.021 (2)	0.0047 (15)	0.0052 (17)	0.0040 (16)
C15	0.038 (2)	0.024 (2)	0.024 (2)	−0.0020 (18)	0.0140 (19)	−0.0055 (17)
C16	0.037 (2)	0.030 (2)	0.029 (2)	−0.0050 (18)	0.0176 (19)	−0.0007 (18)
C17	0.034 (2)	0.018 (2)	0.027 (2)	−0.0033 (16)	0.0074 (18)	−0.0001 (17)
C18	0.030 (2)	0.022 (2)	0.021 (2)	−0.0001 (16)	0.0093 (17)	−0.0026 (16)
C19	0.025 (2)	0.022 (2)	0.024 (2)	0.0063 (16)	0.0098 (17)	0.0028 (17)

Geometric parameters (Å, º) top

Br1—C17	1.898 (4)	C5—H5C	0.9800
Cl1—C10	1.751 (4)	C6—C7	1.529 (5)
O1—C2	1.339 (4)	C6—H6	1.0000
O1—C1	1.445 (5)	C7—C8	1.390 (5)
O2—C2	1.214 (4)	C7—C12	1.391 (5)
N1—C13	1.315 (4)	C8—C9	1.382 (5)
N1—C6	1.479 (4)	C8—H8	0.9500
N1—H1	0.8800	C9—C10	1.377 (5)
N2—C13	1.357 (4)	C9—H9	0.9500
N2—C4	1.386 (5)	C10—C11	1.381 (5)
N2—H2	0.8800	C11—C12	1.377 (5)
N3—C13	1.330 (4)	C11—H11	0.9500
N3—C14	1.428 (4)	C12—H12	0.9500
N3—H3	0.8800	C14—C15	1.377 (5)
C1—H1A	0.9800	C14—C19	1.395 (5)
C1—H1B	0.9800	C15—C16	1.395 (5)
C1—H1C	0.9800	C15—H15	0.9500
C2—C3	1.475 (5)	C16—C17	1.381 (5)
C3—C4	1.349 (5)	C16—H16	0.9500
C3—C6	1.510 (5)	C17—C18	1.373 (5)
C4—C5	1.500 (5)	C18—C19	1.374 (5)
C5—H5A	0.9800	C18—H18	0.9500
C5—H5B	0.9800	C19—H19	0.9500

C2—O1—C1	116.1 (3)	C8—C7—C6	122.3 (3)
C13—N1—C6	120.9 (3)	C12—C7—C6	119.6 (3)
C13—N1—H1	119.6	C9—C8—C7	121.5 (4)
C6—N1—H1	119.6	C9—C8—H8	119.3
C13—N2—C4	122.4 (3)	C7—C8—H8	119.3
C13—N2—H2	118.8	C10—C9—C8	118.5 (4)
C4—N2—H2	118.8	C10—C9—H9	120.7
C13—N3—C14	127.0 (3)	C8—C9—H9	120.7
C13—N3—H3	116.5	C9—C10—C11	121.9 (4)
C14—N3—H3	116.5	C9—C10—Cl1	119.5 (3)
O1—C1—H1A	109.5	C11—C10—Cl1	118.6 (3)
O1—C1—H1B	109.5	C12—C11—C10	118.4 (4)
H1A—C1—H1B	109.5	C12—C11—H11	120.8
O1—C1—H1C	109.5	C10—C11—H11	120.8
H1A—C1—H1C	109.5	C11—C12—C7	121.6 (4)
H1B—C1—H1C	109.5	C11—C12—H12	119.2
O2—C2—O1	122.6 (4)	C7—C12—H12	119.2
O2—C2—C3	126.2 (4)	N1—C13—N3	124.0 (3)
O1—C2—C3	111.1 (3)	N1—C13—N2	118.3 (3)
C4—C3—C2	122.2 (3)	N3—C13—N2	117.6 (3)
C4—C3—C6	118.7 (3)	C15—C14—C19	120.1 (3)
C2—C3—C6	119.0 (3)	C15—C14—N3	118.2 (3)
C3—C4—N2	118.3 (3)	C19—C14—N3	121.6 (3)
C3—C4—C5	128.8 (4)	C14—C15—C16	120.1 (4)
N2—C4—C5	112.9 (3)	C14—C15—H15	120.0
C4—C5—H5A	109.5	C16—C15—H15	120.0
C4—C5—H5B	109.5	C17—C16—C15	118.8 (4)
H5A—C5—H5B	109.5	C17—C16—H16	120.6
C4—C5—H5C	109.5	C15—C16—H16	120.6
H5A—C5—H5C	109.5	C18—C17—C16	121.4 (4)
H5B—C5—H5C	109.5	C18—C17—Br1	118.9 (3)
N1—C6—C3	108.8 (3)	C16—C17—Br1	119.7 (3)
N1—C6—C7	110.0 (3)	C17—C18—C19	119.8 (3)
C3—C6—C7	115.3 (3)	C17—C18—H18	120.1
N1—C6—H6	107.5	C19—C18—H18	120.1
C3—C6—H6	107.5	C18—C19—C14	119.9 (3)
C7—C6—H6	107.5	C18—C19—H19	120.1
C8—C7—C12	118.0 (4)	C14—C19—H19	120.1

C1—O1—C2—O2	−2.1 (5)	C8—C9—C10—C11	0.6 (6)
C1—O1—C2—C3	178.1 (3)	C8—C9—C10—Cl1	−177.6 (3)
O2—C2—C3—C4	−3.4 (6)	C9—C10—C11—C12	1.4 (6)
O1—C2—C3—C4	176.4 (3)	Cl1—C10—C11—C12	179.7 (3)
O2—C2—C3—C6	179.9 (4)	C10—C11—C12—C7	−2.6 (6)
O1—C2—C3—C6	−0.3 (5)	C8—C7—C12—C11	1.6 (5)
C2—C3—C4—N2	175.7 (3)	C6—C7—C12—C11	177.4 (3)
C6—C3—C4—N2	−7.6 (5)	C6—N1—C13—N3	−168.9 (3)
C2—C3—C4—C5	−4.6 (6)	C6—N1—C13—N2	15.6 (5)
C6—C3—C4—C5	172.2 (3)	C14—N3—C13—N1	18.7 (6)
C13—N2—C4—C3	−18.5 (5)	C14—N3—C13—N2	−165.8 (3)
C13—N2—C4—C5	161.7 (3)	C4—N2—C13—N1	14.7 (5)
C13—N1—C6—C3	−37.3 (4)	C4—N2—C13—N3	−161.0 (3)
C13—N1—C6—C7	89.8 (4)	C13—N3—C14—C15	−146.4 (4)
C4—C3—C6—N1	32.5 (4)	C13—N3—C14—C19	38.7 (5)
C2—C3—C6—N1	−150.7 (3)	C19—C14—C15—C16	1.2 (5)
C4—C3—C6—C7	−91.6 (4)	N3—C14—C15—C16	−173.8 (3)
C2—C3—C6—C7	85.3 (4)	C14—C15—C16—C17	−0.7 (6)
N1—C6—C7—C8	−139.6 (3)	C15—C16—C17—C18	−0.9 (6)
C3—C6—C7—C8	−16.2 (5)	C15—C16—C17—Br1	178.5 (3)
N1—C6—C7—C12	44.8 (4)	C16—C17—C18—C19	1.9 (6)
C3—C6—C7—C12	168.2 (3)	Br1—C17—C18—C19	−177.4 (3)
C12—C7—C8—C9	0.5 (5)	C17—C18—C19—C14	−1.4 (5)
C6—C7—C8—C9	−175.2 (3)	C15—C14—C19—C18	−0.1 (5)
C7—C8—C9—C10	−1.5 (6)	N3—C14—C19—C18	174.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2	0.88	2.34	3.136 (3)	151
N2—H2···Cl2ⁱ	0.88	2.41	3.179 (3)	146
N3—H3···Cl2ⁱ	0.88	2.39	3.191 (3)	151
C5—H5A···O2	0.98	2.22	2.897 (5)	125
C15—H15···O2ⁱⁱ	0.95	2.42	3.197 (5)	139
C18—H18···Cl2ⁱⁱⁱ	0.95	2.81	3.702 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈BrClN₃O₂⁺·Cl⁻
M_r	471.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.2691 (15), 11.0965 (12), 14.9545 (17)
β (°)	114.181 (3)
V (Å³)	2008.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.33
Crystal size (mm)	0.08 × 0.05 × 0.03

Data collection
Diffractometer	Bruker Kappa DUO APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.835, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	10242, 3919, 2511
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.096, 0.95
No. of reflections	3919
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.40

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2	0.8800	2.3400	3.136 (3)	151.00
N2—H2···Cl2ⁱ	0.8800	2.4100	3.179 (3)	146.00
N3—H3···Cl2ⁱ	0.8800	2.3900	3.191 (3)	151.00
C5—H5A···O2	0.9800	2.2200	2.897 (5)	125.00
C15—H15···O2ⁱⁱ	0.9500	2.4200	3.197 (5)	139.00
C18—H18···Cl2ⁱⁱⁱ	0.9500	2.8100	3.702 (4)	156.00

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

Acknowledgements

The authors thank Durban University of Technology for facilities. KNV thanks the NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship.

References

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 (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef 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
Venugopala, K. N., Nayak, S. K. & Odhav, B. (2012). Acta Cryst. E68, o2977–o2978. CSD CrossRef CAS IUCr Journals Google Scholar
Venugopala, K. N., Nayak, S. K., Pillay, M., Renuka, P., Coovadia, Y. M. & Odhav, B. (2012). Chem. Biol. Drug Des. 81, 219–227. Web of Science PubMed Google Scholar

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Volume 69| Part 4| April 2013| Pages o518-o519

doi:10.1107/S1600536813006296

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

2-(4-Bromo­anilino)-6-(4-chloro­phen­yl)-5-meth­­oxy­carbonyl-4-methyl-3,6-di­hydro­pyrimidin-1-ium chloride

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(4-Bromoanilino)-6-(4-chlorophenyl)-5-methoxycarbonyl-4-methyl-3,6-dihydropyrimidin-1-ium chloride