Crystal structure of (2-methyl-4-phenyl-4H-benzo[4,5]thia­zolo[3,2-a]pyrimidin-3-yl)(phen­yl)methanone

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

doi:10.1107/S2056989015006428

organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o276-o277

https://doi.org/10.1107/S2056989015006428

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Crystal structure of (2-methyl-4-phenyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)(phenyl)methanone

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 27 March 2015; accepted 30 March 2015; online 2 April 2015)

In the title compound, C₂₄H₁₈N₂OS, the pyrimidine ring has a flat envelope conformation with the methine C atom as the flap. The attached phenyl and benzoyl rings are inclined to the mean plane of the pyrimidine ring by 84.87 (8) and 75.33 (9)°, respectively. The benzothiazolo group is planar (r.m.s. deviation = 0.009 Å) and inclined to the mean plane of the pyrimidine ring by 3.27 (6)°. In the crystal, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers.

Keywords: crystal structure; pyrimidine; benzo; thiazolo; C—H⋯N hydrogen bonding.

CCDC reference: 1056199

1. Related literature

For general background to the biological activities of pyrimidine derivatives, see: Kumar et al. (2002 ); Baraldi et al. (2002 ); Nasr & Gineinah (2002 ). For literature on the synthesis of fused benzothiazolo derivatives, see: Nagarapu et al. (2013a ,b ).

2. Experimental

2.1. Crystal data

C₂₄H₁₈N₂OS
M_r = 382.46
Monoclinic, P 2₁ /c
a = 12.1894 (6) Å
b = 18.6119 (8) Å
c = 8.9370 (4) Å
β = 110.360 (1)°
V = 1900.85 (15) Å³
Z = 4
Cu Kα radiation
μ = 1.64 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.18 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.709, T_max = 0.745
11594 measured reflections
3090 independent reflections
3047 reflections with I > 2σ(I)
R_int = 0.036

2.3. Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.08
3090 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯N1ⁱ	0.93	2.56	3.472 (2)	166
Symmetry code: (i) -x+2, -y+1, -z+1.

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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1056199

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015006428/su5105sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006428/su5105Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015006428/su5105Isup3.cml

checkCIF report

Synthesis and crystallization top

A mixture of benzaldehyde was treated with 1-phenyl butane 1-3-dione 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 to yellow. It was kept aside overnight at room temperature. On completion of reaction (monitored by TLC) the solid obtained was separated and purified by column chromatography using hexane and ethyl acetate as eluent. The solid obtained was recrystallized using a 1:1 mixture of ethanol and THF giving yellow block-like crystals.

Structural commentary top

Many pyrimidine derivatives show strong activity against bacteria, tumor and some viruses (Kumar et al., 2012; Baraldi et al., 2002; Nasr & Gineinah, 2002). Owing to the above said important properties of pyrimidine derivatives,the crystal structure determination of the title compound is carried out.

The molecular structure of the title compound is shown in Fig. 1. The pyrimidine ring [N1/C2/N19/C11—C13] has a envelope conformation with the maximum deviation of 0.1342 (17) Å shown by the flap atom C11. The attached phenyl ring [C15—C20] is twisted at an angle of 84.87 (8) ° with respect to pyrimidine ring mean plane. The thiazolo group [S3/C2/N10/C4/C9] is also planar and fused with a benzene ring [C4—C9]. The phenylmethanone ring [C23—C28] is almost perpendicular to the pyrimidine ring mean plane, with a dihedral angle between of 75.33 (9) Å.

In the crystal, molecules are linked via pairs of C—H···N hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H = 0.93-0.98 Å) and allowed to ride on their parent atoms, 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 to the biological activities of pyrimidine derivatives, see: Kumar et al. (2002); Baraldi et al. (2002); Nasr & Gineinah (2002). For literature on the synthesis of fused benzothiazolo derivatives, see: Nagarapu et al. (2013a,b).

Structure description top

In the crystal, molecules are linked via pairs of C—H···N hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

For general background to the biological activities of pyrimidine derivatives, see: Kumar et al. (2002); Baraldi et al. (2002); Nasr & Gineinah (2002). For literature on the synthesis of fused benzothiazolo derivatives, see: Nagarapu et al. (2013a,b).

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); 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. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

(2-Methyl-4-phenyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)(phenyl)methanone top

Crystal data top

C₂₄H₁₈N₂OS	F(000) = 800
M_r = 382.46	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3047 reflections
a = 12.1894 (6) Å	θ = 4.8–64.4°
b = 18.6119 (8) Å	µ = 1.64 mm⁻¹
c = 8.9370 (4) Å	T = 296 K
β = 110.360 (1)°	Block, yellow
V = 1900.85 (15) Å³	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	3047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and φ scans	θ_max = 64.4°, θ_min = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→12
T_min = 0.709, T_max = 0.745	k = −21→19
11594 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0592P)² + 1.0365P] where P = (F_o² + 2F_c²)/3
3090 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₁₈N₂OS	V = 1900.85 (15) Å³
M_r = 382.46	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.1894 (6) Å	µ = 1.64 mm⁻¹
b = 18.6119 (8) Å	T = 296 K
c = 8.9370 (4) Å	0.25 × 0.20 × 0.18 mm
β = 110.360 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3090 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3047 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.745	R_int = 0.036
11594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	Δρ_max = 0.28 e Å⁻³
3090 reflections	Δρ_min = −0.33 e Å⁻³
254 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
S3	0.78290 (4)	0.78385 (2)	0.29579 (5)	0.02105 (16)
O22	0.63518 (10)	0.46696 (6)	−0.01765 (14)	0.0218 (3)
N10	0.67761 (11)	0.66193 (7)	0.23307 (16)	0.0153 (3)
N1	0.86815 (12)	0.66330 (7)	0.21581 (17)	0.0185 (3)
C23	0.81232 (14)	0.42002 (9)	0.1606 (2)	0.0176 (4)
C15	0.66359 (13)	0.54627 (9)	0.36319 (19)	0.0158 (3)
C21	0.72853 (14)	0.47969 (9)	0.08872 (18)	0.0159 (3)
C9	0.59793 (14)	0.70747 (9)	0.26642 (19)	0.0168 (4)
C13	0.85112 (14)	0.59148 (9)	0.16452 (19)	0.0166 (3)
C20	0.59791 (15)	0.48448 (9)	0.3530 (2)	0.0199 (4)
H20	0.5447	0.4701	0.2549	0.024*
C8	0.48789 (15)	0.68936 (9)	0.2670 (2)	0.0212 (4)
H8	0.4588	0.6430	0.2427	0.025*
C12	0.75429 (14)	0.55374 (9)	0.15422 (18)	0.0156 (3)
C11	0.65887 (13)	0.58425 (8)	0.20997 (19)	0.0151 (3)
H11	0.5823	0.5756	0.1275	0.018*
C24	0.81031 (16)	0.35791 (9)	0.0720 (2)	0.0239 (4)
H24	0.7608	0.3552	−0.0339	0.029*
C2	0.78084 (14)	0.69288 (9)	0.24274 (19)	0.0161 (3)
C5	0.57494 (15)	0.83013 (9)	0.3392 (2)	0.0220 (4)
H5	0.6034	0.8767	0.3622	0.026*
C7	0.42230 (16)	0.74266 (10)	0.3051 (2)	0.0246 (4)
H7	0.3483	0.7316	0.3068	0.030*
C6	0.46508 (16)	0.81215 (10)	0.3406 (2)	0.0242 (4)
H6	0.4195	0.8469	0.3656	0.029*
C28	0.88470 (15)	0.42280 (10)	0.3196 (2)	0.0229 (4)
H28	0.8869	0.4641	0.3792	0.027*
C18	0.68805 (17)	0.46582 (10)	0.6348 (2)	0.0276 (4)
H18	0.6972	0.4385	0.7255	0.033*
C25	0.88206 (18)	0.30017 (10)	0.1416 (3)	0.0308 (4)
H25	0.8824	0.2595	0.0814	0.037*
C14	0.95013 (15)	0.56424 (10)	0.1177 (2)	0.0229 (4)
H14A	0.9323	0.5167	0.0744	0.034*
H14B	1.0204	0.5630	0.2099	0.034*
H14C	0.9612	0.5955	0.0388	0.034*
C4	0.64142 (15)	0.77729 (9)	0.30278 (19)	0.0183 (4)
C16	0.74035 (15)	0.56846 (9)	0.5113 (2)	0.0219 (4)
H16	0.7840	0.6102	0.5191	0.026*
C17	0.75201 (16)	0.52884 (10)	0.6466 (2)	0.0257 (4)
H17	0.8026	0.5442	0.7455	0.031*
C27	0.95393 (16)	0.36400 (11)	0.3900 (2)	0.0297 (4)
H27	1.0008	0.3656	0.4972	0.036*
C26	0.95303 (17)	0.30319 (11)	0.3006 (3)	0.0307 (4)
H26	1.0002	0.2642	0.3475	0.037*
C19	0.61111 (17)	0.44390 (10)	0.4884 (2)	0.0269 (4)
H19	0.5681	0.4019	0.4805	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S3	0.0211 (3)	0.0137 (3)	0.0288 (3)	−0.00246 (15)	0.00924 (19)	−0.00270 (15)
O22	0.0202 (6)	0.0214 (6)	0.0200 (6)	0.0014 (5)	0.0022 (5)	−0.0039 (5)
N10	0.0169 (7)	0.0114 (7)	0.0184 (7)	−0.0003 (5)	0.0070 (5)	−0.0001 (5)
N1	0.0174 (7)	0.0168 (7)	0.0215 (7)	−0.0005 (5)	0.0071 (6)	0.0008 (6)
C23	0.0164 (8)	0.0159 (8)	0.0229 (8)	0.0006 (6)	0.0099 (7)	0.0014 (7)
C15	0.0152 (8)	0.0152 (8)	0.0188 (8)	0.0035 (6)	0.0080 (6)	−0.0007 (6)
C21	0.0175 (8)	0.0189 (9)	0.0135 (7)	0.0002 (6)	0.0082 (6)	0.0001 (6)
C9	0.0189 (8)	0.0161 (8)	0.0147 (8)	0.0033 (6)	0.0049 (6)	0.0001 (6)
C13	0.0166 (8)	0.0172 (8)	0.0150 (8)	0.0029 (6)	0.0041 (6)	0.0022 (6)
C20	0.0222 (8)	0.0180 (8)	0.0189 (8)	−0.0025 (7)	0.0064 (7)	−0.0014 (7)
C8	0.0217 (9)	0.0168 (9)	0.0265 (9)	−0.0008 (7)	0.0101 (7)	−0.0017 (7)
C12	0.0162 (8)	0.0161 (8)	0.0145 (8)	0.0030 (6)	0.0053 (6)	0.0014 (6)
C11	0.0150 (8)	0.0128 (8)	0.0168 (8)	−0.0002 (6)	0.0046 (6)	−0.0018 (6)
C24	0.0280 (9)	0.0201 (9)	0.0260 (9)	0.0026 (7)	0.0123 (7)	−0.0012 (7)
C2	0.0174 (8)	0.0151 (8)	0.0147 (8)	−0.0005 (6)	0.0041 (6)	0.0012 (6)
C5	0.0278 (9)	0.0147 (8)	0.0223 (9)	0.0020 (7)	0.0072 (7)	−0.0031 (7)
C7	0.0220 (9)	0.0246 (10)	0.0300 (9)	0.0031 (7)	0.0127 (7)	−0.0015 (7)
C6	0.0276 (9)	0.0203 (9)	0.0263 (9)	0.0071 (7)	0.0114 (7)	−0.0018 (7)
C28	0.0216 (9)	0.0210 (9)	0.0244 (9)	0.0016 (7)	0.0059 (7)	0.0008 (7)
C18	0.0384 (11)	0.0250 (10)	0.0222 (9)	0.0030 (8)	0.0140 (8)	0.0063 (7)
C25	0.0378 (11)	0.0180 (9)	0.0442 (12)	0.0065 (8)	0.0238 (9)	−0.0002 (8)
C14	0.0206 (9)	0.0223 (9)	0.0294 (9)	0.0014 (7)	0.0131 (7)	0.0012 (7)
C4	0.0204 (9)	0.0168 (8)	0.0164 (8)	0.0009 (6)	0.0048 (7)	0.0003 (6)
C16	0.0238 (9)	0.0201 (9)	0.0212 (9)	−0.0032 (7)	0.0070 (7)	−0.0025 (7)
C17	0.0294 (9)	0.0280 (10)	0.0172 (8)	0.0009 (8)	0.0050 (7)	−0.0016 (7)
C27	0.0247 (9)	0.0303 (10)	0.0311 (10)	0.0073 (8)	0.0060 (8)	0.0094 (8)
C26	0.0267 (10)	0.0237 (10)	0.0452 (12)	0.0110 (8)	0.0171 (9)	0.0126 (8)
C19	0.0353 (10)	0.0210 (9)	0.0271 (10)	−0.0060 (8)	0.0143 (8)	0.0021 (7)

Geometric parameters (Å, º) top

S3—C4	1.7515 (18)	C24—C25	1.389 (3)
S3—C2	1.7560 (16)	C24—H24	0.9300
O22—C21	1.225 (2)	C5—C4	1.383 (2)
N10—C2	1.359 (2)	C5—C6	1.385 (3)
N10—C9	1.397 (2)	C5—H5	0.9300
N10—C11	1.467 (2)	C7—C6	1.389 (3)
N1—C2	1.293 (2)	C7—H7	0.9300
N1—C13	1.405 (2)	C6—H6	0.9300
C23—C28	1.389 (2)	C28—C27	1.391 (3)
C23—C24	1.396 (2)	C28—H28	0.9300
C23—C21	1.494 (2)	C18—C19	1.380 (3)
C15—C20	1.386 (2)	C18—C17	1.392 (3)
C15—C16	1.391 (2)	C18—H18	0.9300
C15—C11	1.524 (2)	C25—C26	1.384 (3)
C21—C12	1.488 (2)	C25—H25	0.9300
C9—C8	1.385 (2)	C14—H14A	0.9600
C9—C4	1.398 (2)	C14—H14B	0.9600
C13—C12	1.349 (2)	C14—H14C	0.9600
C13—C14	1.497 (2)	C16—C17	1.381 (3)
C20—C19	1.388 (3)	C16—H16	0.9300
C20—H20	0.9300	C17—H17	0.9300
C8—C7	1.389 (3)	C27—C26	1.383 (3)
C8—H8	0.9300	C27—H27	0.9300
C12—C11	1.525 (2)	C26—H26	0.9300
C11—H11	0.9800	C19—H19	0.9300

C4—S3—C2	91.18 (8)	C4—C5—H5	120.7
C2—N10—C9	115.23 (13)	C6—C5—H5	120.7
C2—N10—C11	121.47 (13)	C8—C7—C6	121.25 (17)
C9—N10—C11	122.83 (13)	C8—C7—H7	119.4
C2—N1—C13	115.35 (14)	C6—C7—H7	119.4
C28—C23—C24	119.38 (16)	C5—C6—C7	120.67 (16)
C28—C23—C21	120.53 (15)	C5—C6—H6	119.7
C24—C23—C21	119.81 (15)	C7—C6—H6	119.7
C20—C15—C16	119.38 (16)	C23—C28—C27	120.18 (17)
C20—C15—C11	119.04 (14)	C23—C28—H28	119.9
C16—C15—C11	121.31 (15)	C27—C28—H28	119.9
O22—C21—C12	119.75 (14)	C19—C18—C17	119.92 (17)
O22—C21—C23	120.07 (15)	C19—C18—H18	120.0
C12—C21—C23	120.03 (13)	C17—C18—H18	120.0
C8—C9—N10	126.81 (15)	C26—C25—C24	119.97 (18)
C8—C9—C4	120.99 (15)	C26—C25—H25	120.0
N10—C9—C4	112.20 (14)	C24—C25—H25	120.0
C12—C13—N1	122.97 (15)	C13—C14—H14A	109.5
C12—C13—C14	125.18 (15)	C13—C14—H14B	109.5
N1—C13—C14	111.81 (14)	H14A—C14—H14B	109.5
C15—C20—C19	120.36 (16)	C13—C14—H14C	109.5
C15—C20—H20	119.8	H14A—C14—H14C	109.5
C19—C20—H20	119.8	H14B—C14—H14C	109.5
C9—C8—C7	117.90 (16)	C5—C4—C9	120.64 (16)
C9—C8—H8	121.1	C5—C4—S3	128.57 (14)
C7—C8—H8	121.1	C9—C4—S3	110.79 (12)
C13—C12—C21	124.69 (15)	C17—C16—C15	120.32 (16)
C13—C12—C11	122.17 (15)	C17—C16—H16	119.8
C21—C12—C11	113.13 (13)	C15—C16—H16	119.8
N10—C11—C15	112.04 (13)	C16—C17—C18	119.97 (16)
N10—C11—C12	108.29 (13)	C16—C17—H17	120.0
C15—C11—C12	109.03 (12)	C18—C17—H17	120.0
N10—C11—H11	109.1	C26—C27—C28	120.05 (18)
C15—C11—H11	109.1	C26—C27—H27	120.0
C12—C11—H11	109.1	C28—C27—H27	120.0
C25—C24—C23	120.18 (17)	C27—C26—C25	120.19 (17)
C25—C24—H24	119.9	C27—C26—H26	119.9
C23—C24—H24	119.9	C25—C26—H26	119.9
N1—C2—N10	127.70 (15)	C18—C19—C20	120.02 (17)
N1—C2—S3	121.70 (13)	C18—C19—H19	120.0
N10—C2—S3	110.59 (12)	C20—C19—H19	120.0
C4—C5—C6	118.55 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1ⁱ	0.93	2.56	3.472 (2)	166

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1ⁱ	0.93	2.563	3.472 (2)	166

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

The authors are thankful to 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
Nagarapu, L., Gaikwad, H. K., Palem, J. D., Venkatesh, R., Bantu, R. & Sridhar, B. (2013a). Synth. Commun. 43, 93–104. CSD CrossRef CAS Google Scholar
Nagarapu, L., Vanaparthi, S., Bantu, R. & Kumar, C. G. (2013b). Eur. J. Med. Chem. 69, 817–822. Web of Science CrossRef CAS PubMed 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 o276-o277

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

Crystal structure of (2-methyl-4-phenyl-4H-benzo[4,5]thia­zolo[3,2-a]pyrimidin-3-yl)(phen­yl)methanone

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 (2-methyl-4-phenyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)(phenyl)methanone