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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1257-o1258

Methyl 2-(2-bromo­benzyl­­idene)-5-(4-hy­dr­oxy­phen­yl)-7-methyl-3-oxo-2,3-di­hydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: noorsb@rediffmail.com

(Received 5 March 2012; accepted 27 March 2012; online 31 March 2012)

In the title compound, C22H17BrN2O4S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The meth­oxy­carbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O—H⋯N and C—H⋯S inter­actions result in sheets along the c axis. The supra­molecular assembly is stabilized by ππ stacking inter­actions between the 2-bromo­benzyl­idene and thia­zolopyrimidine rings [centroid–centroid distance = 3.632 (1) Å]. In addition, C—H⋯π inter­actions are also observed in the crystal structure.

Related literature

For therapeutic and medicinal properties of thia­zolopyrimidine derivatives, see: Kappe (2000[Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.]); Ozair et al. (2010[Ozair, A., Suroor, A. K., Nadeem, S. & Waquar, A. (2010). Med. Chem. Res. 19, 1245-1258.]). For a related structure, see: Nagarajaiah & Begum (2011[Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17BrN2O4S

  • Mr = 485.35

  • Monoclinic, P 21 /c

  • a = 9.851 (2) Å

  • b = 23.461 (6) Å

  • c = 9.416 (2) Å

  • β = 111.229 (5)°

  • V = 2028.5 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.16 mm−1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS, Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]) Tmin = 0.697, Tmax = 0.724

  • 12267 measured reflections

  • 4409 independent reflections

  • 2563 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.178

  • S = 1.04

  • 4409 reflections

  • 286 parameters

  • H-atom parameters constrained

  • Δρmax = 1.04 e Å−3

  • Δρmin = −0.87 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4⋯N2i 0.82 1.96 2.782 (4) 178
C4B—H4B1⋯S1ii 0.96 2.80 3.621 (12) 144
C1—H1CCg1iii 0.96 2.78 3.585 (5) 142
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1; (iii) [x-1, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The title compound is a representative of thiazolopyrimidine derivatives, which have recently emerged as target molecules due to their therapeutic and medicinal properties (Kappe, 2000) such as anti-inflammatory and antinociceptive activities (Ozair et al. 2010) in addition to being calcium channel blockers.

In the title molecule (Fig. 1), the 4-hydroxy-phenyl group adopts a psuedo synperiplanar conformation with respect to C5—H5 bond. The central pyrimidine ring with a chiral C5 atom is significantly puckered and adopts a half chair conformation with C5 displaced from the mean plane of the remaining ring atoms (C6/C7/C9//N2/N1) by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it with a dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The methoxycarbonyl group in the title compound is disordered in which the carbon atoms C8, C4 and the oxygen atoms O2 and O3 are located over two sites (C8A/C8B,C4A/C4B, O2A/O2B and O3A/O3B) with site occupancy ratio 0.568 (5):0.432 (5) resulting in a major and a minor conformers. The crystal structure is primarily stabilized by intermolecular O4—H4···N2 and C4B—H4B1···S1 interactions which result in two dimensional sheets along the c-axis (Fig. 2). The molecular packing is further stabilized by ππ stacking interactions between the thiazolopyrimidine and 2-bromo-benzylidene rings. The C3···C21 (x - 1, y, z - 1) disposed at a distance of 3.632 (1) Å. In addition C1—H1···Cg1 interactions (Cg1 being the centroid of the benzene ring C10–C15, Table 1) are also observed. The bond lengths and angles in the title molecule are in close agreement with the corresponding bond lengths and angles reported in a similar compound (Nagarajaiah & Begum, 2011).

Related literature top

For therapeutic and medicinal properties of thiazolopyrimidine derivatives, see: Kappe (2000); Ozair et al. (2010). For a related structure, see: Nagarajaiah & Begum (2011).

Experimental top

A mixture of 4-(4-hydroxy-phenyl)-6-methyl-2-thioxo-1,2,3, 4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester (0.01 mol), chloroaceticacid (0.01 mol), 2-bromo benzaldehyde (0.01 mol) and sodium acetate (1.5 g) was taken in a mixture of glacial acetic acid and acetic anhydride (25 ml; 1:1) and refluxed for 10 hr. The reaction mixture was concentrated and the solid thus obtained was filtered and recrystallized with ethyl acetate to get the title compound (yield = 78%, m.p. 468–470 K). The compound was recrystallized by slow evaporation of an ethyl acetate-ethanol (6:4) solution, yielding pale yellow single crystals suitable for X-ray diffraction.

Refinement top

The H atoms were placed at calculated positions in the riding model approximation with O—H = 0.82 Å and C—H = 0.93, 0.96 and 0.98 Å for aryl, methyl and methyne H-atoms respectively, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C/O) for other H atom.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the intermolecular hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.
Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro- 5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate top
Crystal data top
C22H17BrN2O4SF(000) = 984
Mr = 485.35Dx = 1.589 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4409 reflections
a = 9.851 (2) Åθ = 2.2–27.0°
b = 23.461 (6) ŵ = 2.16 mm1
c = 9.416 (2) ÅT = 296 K
β = 111.229 (5)°Block, yellow
V = 2028.5 (8) Å30.18 × 0.16 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEX CCD detector
diffractometer
4409 independent reflections
Radiation source: fine-focus sealed tube2563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS, Bruker, 1998)
h = 127
Tmin = 0.697, Tmax = 0.724k = 2829
12267 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0878P)2]
where P = (Fo2 + 2Fc2)/3
4409 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 1.04 e Å3
0 restraintsΔρmin = 0.87 e Å3
Crystal data top
C22H17BrN2O4SV = 2028.5 (8) Å3
Mr = 485.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.851 (2) ŵ = 2.16 mm1
b = 23.461 (6) ÅT = 296 K
c = 9.416 (2) Å0.18 × 0.16 × 0.16 mm
β = 111.229 (5)°
Data collection top
Bruker SMART APEX CCD detector
diffractometer
4409 independent reflections
Absorption correction: multi-scan
(SADABS, Bruker, 1998)
2563 reflections with I > 2σ(I)
Tmin = 0.697, Tmax = 0.724Rint = 0.054
12267 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.04Δρmax = 1.04 e Å3
4409 reflectionsΔρmin = 0.87 e Å3
286 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 > 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
xyzUiso*/UeqOcc. (<1)
Br10.94209 (7)0.12175 (2)0.43004 (8)0.0693 (3)
S10.69429 (13)0.08352 (5)0.61655 (13)0.0406 (3)
O10.5280 (4)0.00179 (13)0.2404 (4)0.0585 (10)
O40.6120 (3)0.20100 (12)0.1933 (3)0.0375 (7)
H40.57190.18810.27940.056*
N10.4855 (4)0.08217 (14)0.3536 (4)0.0380 (9)
N20.4767 (4)0.15870 (15)0.5130 (4)0.0376 (9)
C10.2725 (5)0.2232 (2)0.4575 (6)0.0498 (12)
H1A0.16880.21800.41900.075*
H1B0.30830.22330.56680.075*
H1C0.29550.25890.42160.075*
C20.6896 (5)0.02716 (17)0.4936 (5)0.0395 (11)
C30.5627 (6)0.03336 (18)0.3500 (5)0.0430 (12)
C50.3714 (5)0.1052 (2)0.2168 (5)0.0434 (12)
H50.30470.07410.16660.052*
C60.2857 (5)0.1505 (2)0.2668 (5)0.0455 (12)
C70.3424 (5)0.17558 (19)0.4030 (5)0.0406 (11)
C90.5358 (5)0.11320 (17)0.4837 (5)0.0348 (10)
C100.4374 (5)0.12880 (17)0.1052 (5)0.0374 (10)
C110.5353 (5)0.17425 (18)0.1479 (5)0.0379 (10)
H110.56120.18930.24560.045*
C120.5942 (5)0.19733 (17)0.0490 (5)0.0348 (10)
H120.66100.22700.08030.042*
C130.5535 (5)0.17610 (17)0.0963 (5)0.0347 (10)
C140.4570 (5)0.13072 (17)0.1407 (5)0.0387 (11)
H140.43060.11580.23860.046*
C150.4003 (6)0.1078 (2)0.0394 (5)0.0466 (12)
H150.33560.07740.06990.056*
C160.7832 (6)0.01649 (18)0.5097 (6)0.0474 (13)
H160.75600.04140.42740.057*
C170.9172 (6)0.03188 (19)0.6303 (6)0.0490 (13)
C180.9740 (6)0.0014 (2)0.7658 (6)0.0521 (13)
H180.92230.02960.78170.063*
C191.1042 (6)0.0158 (2)0.8764 (7)0.0606 (15)
H191.13990.00520.96600.073*
C201.1822 (6)0.0617 (3)0.8549 (8)0.0702 (18)
H201.27110.07110.92950.084*
C211.1297 (7)0.0930 (2)0.7252 (8)0.0658 (17)
H211.18100.12460.71210.079*
C221.0006 (6)0.0778 (2)0.6137 (7)0.0571 (15)
O2A0.0777 (8)0.2032 (3)0.1381 (8)0.0398 (15)0.568 (5)
O3A0.1029 (9)0.1203 (3)0.0273 (9)0.0478 (18)0.568 (5)
C8A0.1483 (11)0.1543 (4)0.1338 (13)0.0344 (18)0.568 (5)
C4A0.0570 (9)0.2119 (4)0.0135 (11)0.055 (2)0.568 (5)
H4A10.09800.24790.02560.083*0.568 (5)
H4A20.03970.21180.08050.083*0.568 (5)
H4A30.12370.18180.01190.083*0.568 (5)
O2B0.0944 (12)0.1436 (4)0.0420 (13)0.0398 (15)0.432 (5)
O3B0.0726 (12)0.2187 (4)0.1889 (12)0.0478 (18)0.432 (5)
C8B0.1406 (17)0.1798 (6)0.1675 (17)0.0344 (18)0.432 (5)
C4B0.0390 (12)0.1602 (5)0.0732 (13)0.055 (2)0.432 (5)
H4B10.06670.13230.15320.083*0.432 (5)
H4B20.11350.16290.03020.083*0.432 (5)
H4B30.02690.19660.11390.083*0.432 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0943 (5)0.0404 (3)0.1033 (6)0.0081 (3)0.0720 (4)0.0062 (3)
S10.0530 (7)0.0361 (6)0.0348 (6)0.0079 (5)0.0185 (5)0.0037 (5)
O10.089 (3)0.0330 (17)0.056 (2)0.0130 (18)0.029 (2)0.0096 (17)
O40.0459 (19)0.0332 (16)0.0337 (16)0.0035 (13)0.0147 (15)0.0014 (13)
N10.050 (2)0.0355 (19)0.030 (2)0.0093 (17)0.0166 (17)0.0013 (16)
N20.044 (2)0.041 (2)0.0301 (19)0.0043 (18)0.0160 (17)0.0071 (16)
C10.043 (3)0.051 (3)0.060 (3)0.008 (2)0.025 (2)0.016 (3)
C20.061 (3)0.026 (2)0.041 (3)0.004 (2)0.031 (2)0.0029 (19)
C30.066 (3)0.023 (2)0.049 (3)0.011 (2)0.031 (3)0.002 (2)
C50.049 (3)0.041 (2)0.036 (3)0.015 (2)0.010 (2)0.000 (2)
C60.038 (3)0.054 (3)0.043 (3)0.009 (2)0.013 (2)0.017 (2)
C70.043 (3)0.040 (2)0.045 (3)0.004 (2)0.023 (2)0.010 (2)
C90.044 (3)0.034 (2)0.030 (2)0.006 (2)0.019 (2)0.0039 (19)
C100.045 (3)0.031 (2)0.033 (2)0.0082 (19)0.011 (2)0.0016 (18)
C110.048 (3)0.037 (2)0.028 (2)0.007 (2)0.012 (2)0.0058 (19)
C120.041 (3)0.029 (2)0.035 (2)0.0046 (19)0.014 (2)0.0005 (18)
C130.042 (3)0.030 (2)0.033 (2)0.0039 (19)0.016 (2)0.0048 (18)
C140.052 (3)0.034 (2)0.029 (2)0.005 (2)0.014 (2)0.0027 (19)
C150.064 (3)0.041 (2)0.031 (2)0.021 (2)0.012 (2)0.004 (2)
C160.069 (4)0.024 (2)0.061 (3)0.004 (2)0.038 (3)0.005 (2)
C170.058 (3)0.030 (2)0.071 (4)0.003 (2)0.038 (3)0.015 (2)
C180.062 (3)0.037 (3)0.063 (3)0.010 (2)0.030 (3)0.016 (3)
C190.066 (4)0.052 (3)0.063 (4)0.004 (3)0.023 (3)0.014 (3)
C200.055 (4)0.071 (4)0.091 (5)0.017 (3)0.035 (3)0.050 (4)
C210.081 (5)0.049 (3)0.092 (5)0.014 (3)0.060 (4)0.031 (3)
C220.069 (4)0.037 (3)0.086 (4)0.008 (3)0.053 (3)0.023 (3)
O2A0.031 (3)0.038 (4)0.048 (3)0.006 (3)0.012 (3)0.003 (3)
O3A0.055 (4)0.027 (3)0.055 (4)0.004 (3)0.013 (3)0.002 (3)
C8A0.037 (4)0.019 (5)0.045 (5)0.015 (5)0.013 (4)0.001 (5)
C4A0.036 (4)0.057 (4)0.063 (5)0.000 (3)0.006 (4)0.013 (4)
O2B0.031 (3)0.038 (4)0.048 (3)0.006 (3)0.012 (3)0.003 (3)
O3B0.055 (4)0.027 (3)0.055 (4)0.004 (3)0.013 (3)0.002 (3)
C8B0.037 (4)0.019 (5)0.045 (5)0.015 (5)0.013 (4)0.001 (5)
C4B0.036 (4)0.057 (4)0.063 (5)0.000 (3)0.006 (4)0.013 (4)
Geometric parameters (Å, º) top
Br1—C221.915 (6)C13—C141.387 (6)
S1—C21.747 (4)C14—C151.377 (7)
S1—C91.753 (5)C14—H140.9300
O1—C31.215 (5)C15—H150.9300
O4—C131.374 (5)C16—C171.441 (7)
O4—H40.8200C16—H160.9300
N1—C91.355 (5)C17—C181.392 (7)
N1—C31.382 (6)C17—C221.397 (7)
N1—C51.472 (6)C18—C191.370 (7)
N2—C91.293 (5)C18—H180.9300
N2—C71.410 (6)C19—C201.378 (8)
C1—C71.497 (6)C19—H190.9300
C1—H1A0.9600C20—C211.357 (9)
C1—H1B0.9600C20—H200.9300
C1—H1C0.9600C21—C221.371 (8)
C2—C161.349 (6)C21—H210.9300
C2—C31.479 (7)O2A—C8A1.348 (11)
C5—C101.527 (6)O2A—C4A1.432 (11)
C5—C61.534 (7)O3A—C8A1.232 (12)
C5—H50.9800C4A—H4A10.9600
C6—C71.336 (7)C4A—H4A20.9600
C6—C8A1.477 (12)C4A—H4A30.9600
C6—C8B1.556 (17)O2B—C8B1.391 (17)
C10—C151.367 (6)O2B—C4B1.423 (15)
C10—C111.396 (6)O3B—C8B1.192 (17)
C11—C121.374 (6)C4B—H4B10.9600
C11—H110.9300C4B—H4B20.9600
C12—C131.373 (6)C4B—H4B30.9600
C12—H120.9300
C2—S1—C991.4 (2)C15—C14—C13119.7 (4)
C13—O4—H4109.5C15—C14—H14120.1
C9—N1—C3116.3 (4)C13—C14—H14120.1
C9—N1—C5120.5 (4)C10—C15—C14121.3 (4)
C3—N1—C5122.4 (4)C10—C15—H15119.3
C9—N2—C7116.8 (4)C14—C15—H15119.3
C7—C1—H1A109.5C2—C16—C17132.3 (5)
C7—C1—H1B109.5C2—C16—H16113.9
H1A—C1—H1B109.5C17—C16—H16113.9
C7—C1—H1C109.5C18—C17—C22116.2 (5)
H1A—C1—H1C109.5C18—C17—C16122.8 (5)
H1B—C1—H1C109.5C22—C17—C16120.9 (5)
C16—C2—C3119.6 (4)C19—C18—C17121.6 (5)
C16—C2—S1130.3 (4)C19—C18—H18119.2
C3—C2—S1110.0 (3)C17—C18—H18119.2
O1—C3—N1122.6 (5)C18—C19—C20120.0 (6)
O1—C3—C2127.0 (4)C18—C19—H19120.0
N1—C3—C2110.5 (4)C20—C19—H19120.0
N1—C5—C10110.8 (4)C21—C20—C19120.3 (6)
N1—C5—C6108.5 (4)C21—C20—H20119.9
C10—C5—C6112.2 (4)C19—C20—H20119.9
N1—C5—H5108.4C20—C21—C22119.5 (6)
C10—C5—H5108.4C20—C21—H21120.2
C6—C5—H5108.4C22—C21—H21120.3
C7—C6—C8A136.4 (6)C21—C22—C17122.4 (6)
C7—C6—C5121.0 (4)C21—C22—Br1116.3 (4)
C8A—C6—C5102.7 (5)C17—C22—Br1121.3 (4)
C7—C6—C8B110.8 (7)C8A—O2A—C4A115.6 (8)
C5—C6—C8B127.6 (7)O3A—C8A—O2A122.4 (10)
C6—C7—N2122.4 (4)O3A—C8A—C6127.0 (9)
C6—C7—C1125.0 (5)O2A—C8A—C6110.5 (8)
N2—C7—C1112.6 (4)O2A—C4A—H4A1109.5
N2—C9—N1126.2 (4)O2A—C4A—H4A2109.5
N2—C9—S1122.0 (3)H4A1—C4A—H4A2109.5
N1—C9—S1111.8 (3)O2A—C4A—H4A3109.5
C15—C10—C11118.0 (4)H4A1—C4A—H4A3109.5
C15—C10—C5121.9 (4)H4A2—C4A—H4A3109.5
C11—C10—C5120.1 (4)C8B—O2B—C4B114.1 (10)
C12—C11—C10121.5 (4)O3B—C8B—O2B125.5 (14)
C12—C11—H11119.2O3B—C8B—C6133.4 (12)
C10—C11—H11119.2O2B—C8B—C6100.8 (10)
C13—C12—C11119.3 (4)O2B—C4B—H4B1109.5
C13—C12—H12120.3O2B—C4B—H4B2109.5
C11—C12—H12120.3H4B1—C4B—H4B2109.5
C12—C13—O4117.8 (4)O2B—C4B—H4B3109.5
C12—C13—C14120.0 (4)H4B1—C4B—H4B3109.5
O4—C13—C14122.2 (4)H4B2—C4B—H4B3109.5
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
O4—H4···N2i0.821.962.782 (4)178
C4B—H4B1···S1ii0.962.803.621 (12)144
C1—H1C···Cg1iii0.962.783.585 (5)142
Symmetry codes: (i) x, y, z1; (ii) x1, y, z1; (iii) x1, y1/2, z3/2.

Experimental details

Crystal data
Chemical formulaC22H17BrN2O4S
Mr485.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.851 (2), 23.461 (6), 9.416 (2)
β (°) 111.229 (5)
V3)2028.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)2.16
Crystal size (mm)0.18 × 0.16 × 0.16
Data collection
DiffractometerBruker SMART APEX CCD detector
diffractometer
Absorption correctionMulti-scan
(SADABS, Bruker, 1998)
Tmin, Tmax0.697, 0.724
No. of measured, independent and
observed [I > 2σ(I)] reflections
12267, 4409, 2563
Rint0.054
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.178, 1.04
No. of reflections4409
No. of parameters286
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.04, 0.87

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
O4—H4···N2i0.821.962.782 (4)178
C4B—H4B1···S1ii0.962.803.621 (12)144
C1—H1C···Cg1iii0.962.783.585 (5)142
Symmetry codes: (i) x, y, z1; (ii) x1, y, z1; (iii) x1, y1/2, z3/2.
 

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

First citationBruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationKappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052.  Web of Science CrossRef PubMed CAS
First citationNagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.  Web of Science CSD CrossRef IUCr Journals
First citationOzair, A., Suroor, A. K., Nadeem, S. & Waquar, A. (2010). Med. Chem. Res. 19, 1245–1258.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

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Volume 68| Part 4| April 2012| Pages o1257-o1258
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