Crystal structure of ethyl 4-(2,4-di­chloro­phen­yl)-2-methyl-4H-benzo[4,5]thia­zolo[3,2-a]pyrimidine-3-carboxyl­ate

Sankar, T.; Naveen, S.; Lokanath, N.K.; Gunasekaran, K.

doi:10.1107/S2056989015007033

organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o306-o307

https://doi.org/10.1107/S2056989015007033

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Crystal structure of ethyl 4-(2,4-dichlorophenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate

T. Sankar,^a S. Naveen,^b N. K. Lokanath ^c and K. Gunasekaran ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: gunaunom@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 April 2015; accepted 8 April 2015; online 15 April 2015)

In the title compound, C₂₀H₁₆Cl₂N₂O₂S, the pyrimidine ring has a screw-boat conformation. The attached dichlorophenyl ring is twisted at an angle of 89.29 (13)° with respect to the pyrimidine ring mean plane. The benzothiazole group is approximately planar (r.m.s. deviation = 0.008 Å) and inclined to the pyrimidine ring mean plane by 3.04 (10)°. The carboxylate group assumes an extended conformation with respect to the pyrimidine ring, which can be seen from the O=C—O—C torsion angle of 3.2 (4) °. In the crystal, molecules are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming slabs lying parallel to (100).

Keywords: crystal structure; pyrimidine; benzothiazole; C—H⋯O hydrogen bonds; C—H⋯N hydrogen bonds.

CCDC reference: 1056200

1. Related literature

For general background and literature on the biological properties of pyrimidine derivatives, see: Kumar et al. (2002 ; Baraldi et al. (2002 ); Nasr & Gineinah (2002 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₆Cl₂N₂O₂S
M_r = 419.31
Monoclinic, C 2/c
a = 38.654 (8) Å
b = 11.787 (3) Å
c = 8.774 (2) Å
β = 102.415 (14)°
V = 3904.1 (15) Å³
Z = 8
Cu Kα radiation
μ = 4.14 mm⁻¹
T = 296 K
0.30 × 0.27 × 0.25 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.370, T_max = 0.424
10089 measured reflections
3114 independent reflections
2519 reflections with I > 2σ(I)
R_int = 0.042

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.04
3114 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1ⁱ	0.93	2.59	3.515 (4)	176
C16—H16⋯O24ⁱⁱ	0.93	2.53	3.180 (4)	128
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ .

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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1056200

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015007033/su5114sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007033/su5114Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007033/su5114Isup3.cml

checkCIF report

Structural commentary top

Many pyrimidine derivatives are reported to have anti-bacterial, anti-tumor and anti-viral activities (Kumar et al., 2012; Baraldi et al., 2002; Nasr et al., 2002). In view of their important properties we synthesized the title compound and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The pyrimidine ring [N1/C13/C12/C11/N10/C2] has a screw-boat conformation and its mean plane is inclined to the planar benzothiazole group [S3/C2/N10/C4—C9; r.m.s. deviation = 0.008 Å] by 3.04 (10) °. The dichlorophenyl ring [C15—C20] is twisted at an angle of 89.29 (13) ° with respect to the pyrimidine ring mean plane. The carboxylate group assumes an extended conformation with respect to the pyrimidine ring, which can be seen from the torsion angle O24—C23—O25—C26 = 3.2 (4) °.

In the crystal, molecules are linked via C—H···O and C—H···N hydrogen bonds forming slabs lying parallel to (100); see Table 1 and Fig. 2.

Synthesis and crystallization top

A mixture of 2,4-dichloro benzaldehyde was treated with ethyl acetoacetate and 2-aminobenzothiazole in the presence of ammonium acetate in ethanol. The mixture was gently warmed in a water bath at 353 K until the colour changed and it was then kept aside overnight at room temperature. The completion of reaction was monitored by TLC. The solid obtained was separated and purified by means of column chromatography using hexane and ethyl acetate as eluent. The sample was recrystallized using a 1:1 mixture of ethanol and THF, yielding yellow block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93-0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Related literature top

For general background and literature on the biological properties of pyrimidine derivatives, see: Kumar et al. (2002; Baraldi et al. (2002); Nasr & Gineinah (2002).

Structure description top

In the crystal, molecules are linked via C—H···O and C—H···N hydrogen bonds forming slabs lying parallel to (100); see Table 1 and Fig. 2.

For general background and literature on the biological properties of pyrimidine derivatives, see: Kumar et al. (2002; Baraldi et al. (2002); Nasr & Gineinah (2002).

Synthesis and crystallization top

Refinement details top

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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed down the c axis.

Ethyl 4-(2,4-dichlorophenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate top

Crystal data top

C₂₀H₁₆Cl₂N₂O₂S	F(000) = 1728
M_r = 419.31	D_x = 1.427 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3114 reflections
a = 38.654 (8) Å	θ = 5.1–64.1°
b = 11.787 (3) Å	µ = 4.14 mm⁻¹
c = 8.774 (2) Å	T = 296 K
β = 102.415 (14)°	Block, yellow
V = 3904.1 (15) Å³	0.30 × 0.27 × 0.25 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	3114 independent reflections
Radiation source: fine-focus sealed tube	2519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and φ scans	θ_max = 64.1°, θ_min = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −43→44
T_min = 0.370, T_max = 0.424	k = −12→12
10089 measured reflections	l = −10→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0772P)² + 2.6744P] where P = (F_o² + 2F_c²)/3
3114 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₁₆Cl₂N₂O₂S	V = 3904.1 (15) Å³
M_r = 419.31	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 38.654 (8) Å	µ = 4.14 mm⁻¹
b = 11.787 (3) Å	T = 296 K
c = 8.774 (2) Å	0.30 × 0.27 × 0.25 mm
β = 102.415 (14)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3114 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2519 reflections with I > 2σ(I)
T_min = 0.370, T_max = 0.424	R_int = 0.042
10089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3114 reflections	Δρ_min = −0.31 e Å⁻³
246 parameters

Special details top

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
N1	0.29291 (6)	0.8365 (2)	0.6499 (3)	0.0540 (6)
C2	0.29669 (6)	0.7278 (2)	0.6518 (3)	0.0450 (6)
S3	0.267722 (17)	0.63964 (6)	0.72345 (9)	0.0552 (3)
C4	0.28999 (6)	0.5193 (2)	0.6806 (3)	0.0446 (6)
C5	0.28233 (7)	0.4079 (2)	0.7057 (3)	0.0520 (7)
H5	0.2631	0.3891	0.7488	0.062*
C6	0.30359 (8)	0.3250 (3)	0.6658 (4)	0.0561 (7)
H6	0.2990	0.2492	0.6832	0.067*
C7	0.33195 (8)	0.3533 (2)	0.5997 (4)	0.0560 (7)
H7	0.3460	0.2958	0.5730	0.067*
C8	0.33984 (7)	0.4649 (2)	0.5723 (3)	0.0484 (7)
H8	0.3589	0.4831	0.5276	0.058*
C9	0.31847 (6)	0.5488 (2)	0.6136 (3)	0.0406 (6)
N10	0.32157 (5)	0.66662 (18)	0.5982 (2)	0.0417 (5)
C11	0.35145 (6)	0.7226 (2)	0.5479 (3)	0.0411 (6)
H11	0.3537	0.6908	0.4474	0.049*
C12	0.34297 (7)	0.8489 (2)	0.5275 (3)	0.0463 (6)
C13	0.31608 (7)	0.8979 (2)	0.5811 (3)	0.0513 (7)
C14	0.30725 (9)	1.0217 (3)	0.5713 (4)	0.0694 (9)
H14A	0.3263	1.0638	0.6345	0.104*
H14B	0.2859	1.0344	0.6084	0.104*
H14C	0.3038	1.0464	0.4649	0.104*
C15	0.38581 (6)	0.7024 (2)	0.6676 (3)	0.0409 (6)
C16	0.38873 (7)	0.7454 (2)	0.8175 (3)	0.0472 (6)
H16	0.3695	0.7836	0.8417	0.057*
C17	0.41907 (8)	0.7332 (3)	0.9307 (4)	0.0608 (8)
H17	0.4205	0.7630	1.0300	0.073*
C18	0.44751 (8)	0.6758 (3)	0.8946 (4)	0.0627 (8)
C19	0.44582 (7)	0.6332 (3)	0.7486 (4)	0.0612 (8)
H19	0.4651	0.5953	0.7251	0.073*
C20	0.41531 (7)	0.6470 (2)	0.6369 (3)	0.0491 (7)
Cl21	0.41503 (2)	0.59197 (7)	0.45153 (10)	0.0706 (3)
Cl22	0.48585 (3)	0.65809 (11)	1.03772 (14)	0.1075 (4)
C23	0.36748 (8)	0.9170 (3)	0.4592 (3)	0.0556 (7)
O24	0.36870 (7)	1.0189 (2)	0.4524 (3)	0.0880 (8)
O25	0.39033 (6)	0.8507 (2)	0.4043 (3)	0.0734 (7)
C26	0.41805 (13)	0.9061 (4)	0.3433 (5)	0.1021 (15)
H26A	0.4088	0.9754	0.2903	0.122*
H26B	0.4253	0.8568	0.2674	0.122*
C27	0.44862 (13)	0.9328 (5)	0.4666 (8)	0.134 (2)
H27A	0.4416	0.9836	0.5400	0.201*
H27B	0.4665	0.9682	0.4221	0.201*
H27C	0.4579	0.8642	0.5190	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0535 (13)	0.0408 (15)	0.0701 (16)	0.0048 (10)	0.0185 (12)	−0.0012 (11)
C2	0.0429 (13)	0.0401 (17)	0.0513 (15)	0.0021 (11)	0.0086 (11)	−0.0025 (12)
S3	0.0456 (4)	0.0476 (5)	0.0771 (5)	0.0017 (3)	0.0239 (3)	0.0002 (3)
C4	0.0394 (12)	0.0424 (17)	0.0512 (15)	−0.0019 (11)	0.0077 (11)	0.0004 (12)
C5	0.0495 (15)	0.0455 (18)	0.0619 (17)	−0.0077 (13)	0.0142 (13)	0.0038 (13)
C6	0.0656 (18)	0.0351 (16)	0.0682 (19)	−0.0063 (13)	0.0155 (15)	0.0017 (13)
C7	0.0608 (17)	0.0400 (18)	0.0682 (19)	0.0019 (13)	0.0163 (15)	−0.0035 (14)
C8	0.0491 (14)	0.0408 (17)	0.0574 (17)	−0.0014 (12)	0.0162 (12)	−0.0049 (13)
C9	0.0420 (13)	0.0351 (15)	0.0429 (14)	−0.0045 (11)	0.0050 (11)	−0.0022 (11)
N10	0.0421 (11)	0.0343 (13)	0.0502 (12)	−0.0013 (9)	0.0136 (10)	−0.0016 (9)
C11	0.0462 (13)	0.0366 (15)	0.0432 (14)	−0.0043 (11)	0.0154 (11)	−0.0037 (11)
C12	0.0538 (15)	0.0379 (16)	0.0450 (15)	−0.0023 (11)	0.0058 (12)	0.0034 (11)
C13	0.0560 (16)	0.0381 (16)	0.0563 (17)	0.0024 (12)	0.0044 (13)	0.0004 (12)
C14	0.075 (2)	0.0404 (19)	0.092 (2)	0.0083 (15)	0.0153 (18)	0.0044 (16)
C15	0.0456 (13)	0.0315 (14)	0.0479 (14)	−0.0041 (11)	0.0152 (11)	−0.0003 (11)
C16	0.0526 (14)	0.0401 (16)	0.0513 (15)	0.0009 (12)	0.0165 (12)	−0.0034 (12)
C17	0.0724 (19)	0.057 (2)	0.0495 (17)	−0.0046 (16)	0.0048 (15)	−0.0073 (14)
C18	0.0493 (16)	0.063 (2)	0.070 (2)	−0.0035 (15)	0.0002 (14)	0.0069 (16)
C19	0.0433 (15)	0.057 (2)	0.085 (2)	0.0012 (13)	0.0171 (15)	0.0003 (17)
C20	0.0490 (14)	0.0414 (16)	0.0623 (17)	−0.0040 (12)	0.0241 (13)	−0.0068 (13)
Cl21	0.0700 (5)	0.0747 (6)	0.0771 (5)	−0.0009 (4)	0.0375 (4)	−0.0252 (4)
Cl22	0.0677 (6)	0.1307 (10)	0.1058 (8)	0.0037 (6)	−0.0221 (5)	0.0064 (7)
C23	0.0678 (18)	0.048 (2)	0.0501 (17)	−0.0049 (14)	0.0103 (14)	0.0078 (13)
O24	0.0960 (18)	0.0479 (16)	0.127 (2)	−0.0077 (12)	0.0385 (16)	0.0245 (14)
O25	0.0905 (16)	0.0654 (16)	0.0767 (15)	−0.0168 (12)	0.0455 (13)	−0.0005 (11)
C26	0.126 (3)	0.104 (3)	0.098 (3)	−0.039 (3)	0.071 (3)	−0.006 (2)
C27	0.088 (3)	0.143 (5)	0.182 (6)	−0.025 (3)	0.050 (4)	−0.008 (4)

Geometric parameters (Å, º) top

N1—C2	1.290 (4)	C14—H14A	0.9600
N1—C13	1.387 (4)	C14—H14B	0.9600
C2—N10	1.364 (3)	C14—H14C	0.9600
C2—S3	1.741 (3)	C15—C20	1.390 (3)
S3—C4	1.741 (3)	C15—C16	1.392 (4)
C4—C5	1.375 (4)	C16—C17	1.372 (4)
C4—C9	1.399 (3)	C16—H16	0.9300
C5—C6	1.369 (4)	C17—C18	1.384 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.387 (4)	C18—C19	1.365 (5)
C6—H6	0.9300	C18—Cl22	1.737 (3)
C7—C8	1.383 (4)	C19—C20	1.371 (4)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.385 (4)	C20—Cl21	1.748 (3)
C8—H8	0.9300	C23—O24	1.204 (4)
C9—N10	1.403 (3)	C23—O25	1.343 (4)
N10—C11	1.478 (3)	O25—C26	1.452 (4)
C11—C15	1.524 (3)	C26—C27	1.455 (7)
C11—C12	1.527 (4)	C26—H26A	0.9700
C11—H11	0.9800	C26—H26B	0.9700
C12—C13	1.358 (4)	C27—H27A	0.9600
C12—C23	1.465 (4)	C27—H27B	0.9600
C13—C14	1.497 (4)	C27—H27C	0.9600

C2—N1—C13	116.2 (2)	C13—C14—H14B	109.5
N1—C2—N10	127.4 (2)	H14A—C14—H14B	109.5
N1—C2—S3	121.2 (2)	C13—C14—H14C	109.5
N10—C2—S3	111.4 (2)	H14A—C14—H14C	109.5
C4—S3—C2	91.26 (12)	H14B—C14—H14C	109.5
C5—C4—C9	121.3 (2)	C20—C15—C16	116.8 (2)
C5—C4—S3	127.6 (2)	C20—C15—C11	124.7 (2)
C9—C4—S3	111.0 (2)	C16—C15—C11	118.4 (2)
C6—C5—C4	118.6 (3)	C17—C16—C15	121.9 (3)
C6—C5—H5	120.7	C17—C16—H16	119.0
C4—C5—H5	120.7	C15—C16—H16	119.0
C5—C6—C7	120.5 (3)	C16—C17—C18	118.9 (3)
C5—C6—H6	119.8	C16—C17—H17	120.6
C7—C6—H6	119.7	C18—C17—H17	120.6
C8—C7—C6	121.6 (3)	C19—C18—C17	121.0 (3)
C8—C7—H7	119.2	C19—C18—Cl22	119.7 (3)
C6—C7—H7	119.2	C17—C18—Cl22	119.3 (3)
C7—C8—C9	117.9 (3)	C18—C19—C20	119.2 (3)
C7—C8—H8	121.1	C18—C19—H19	120.4
C9—C8—H8	121.1	C20—C19—H19	120.4
C8—C9—C4	120.0 (2)	C19—C20—C15	122.2 (3)
C8—C9—N10	127.8 (2)	C19—C20—Cl21	117.0 (2)
C4—C9—N10	112.2 (2)	C15—C20—Cl21	120.9 (2)
C2—N10—C9	114.1 (2)	O24—C23—O25	121.8 (3)
C2—N10—C11	121.4 (2)	O24—C23—C12	127.0 (3)
C9—N10—C11	124.0 (2)	O25—C23—C12	111.2 (3)
N10—C11—C15	110.2 (2)	C23—O25—C26	117.7 (3)
N10—C11—C12	108.0 (2)	O25—C26—C27	111.6 (4)
C15—C11—C12	111.5 (2)	O25—C26—H26A	109.3
N10—C11—H11	109.0	C27—C26—H26A	109.3
C15—C11—H11	109.0	O25—C26—H26B	109.3
C12—C11—H11	109.0	C27—C26—H26B	109.3
C13—C12—C23	121.3 (3)	H26A—C26—H26B	108.0
C13—C12—C11	122.4 (2)	C26—C27—H27A	109.5
C23—C12—C11	116.1 (2)	C26—C27—H27B	109.5
C12—C13—N1	122.9 (3)	H27A—C27—H27B	109.5
C12—C13—C14	125.2 (3)	C26—C27—H27C	109.5
N1—C13—C14	111.9 (3)	H27A—C27—H27C	109.5
C13—C14—H14A	109.5	H27B—C27—H27C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱ	0.93	2.59	3.515 (4)	176
C16—H16···O24ⁱⁱ	0.93	2.53	3.180 (4)	128

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ⁱ	0.93	2.59	3.515 (4)	176
C16—H16···O24ⁱⁱ	0.93	2.53	3.180 (4)	128

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

Acknowledgements

The authors are thankful to the Institution of Excellence, University of Mysore, for providing the single-crystal X-ray diffraction facility.

References

Baraldi, P. G., Pavani, M. G., Nuñez, M. del C., Brigidi, P., Vitali, B., Gambari, R. & Romagnoli, R. (2002). Bioorg. Med. Chem. 10, 449–456. Web of Science CrossRef PubMed CAS 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
Kumar, A., Sinha, S. & Chauhan, P. M. (2002). Bioorg. Med. Chem. Lett. 12, 667-669. Web of Science CrossRef PubMed CAS 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 CSD CrossRef CAS IUCr Journals Google Scholar
Nasr, M. N. & Gineinah, M. M. (2002). Arch. Pharm. Pharm. Med. Chem. 335, 289–295. Web of Science CrossRef CAS 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

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Volume 71| Part 5| May 2015| Pages o306-o307

https://doi.org/10.1107/S2056989015007033

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

Crystal structure of ethyl 4-(2,4-di­chloro­phen­yl)-2-methyl-4H-benzo[4,5]thia­zolo[3,2-a]pyrimidine-3-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 4-(2,4-dichlorophenyl)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate