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

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 benzo-thia-zolo 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, mol-ecules are linked by pairs of C-H⋯N hydrogen bonds, forming inversion dimers.

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 ▸).

Experimental

Crystal data

C24H18N2OS

M = 382.46

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.08

3090 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

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 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006428/su5105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006428/su5105Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006428/su5105Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006428/su5105fig1.tif

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

Click here for additional data file.

a . DOI: 10.1107/S2056989015006428/su5105fig2.tif

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).

CCDC reference: 1056199

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H18N2OS	F(000) = 800
Mr = 382.46	Dx = 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

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

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(Fo2) + (0.0592P)2 + 1.0365P] where P = (Fo2 + 2Fc2)/3
3090 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C27H27N1i	0.93	2.56	3.472(2)	166

Symmetry code: (i) .