Ethyl 2-(4-carb­oxy­benzyl­idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate–N,N-dimethyl­formamide (1/1)

Banu, N.A.; Bheema Raju, V.

doi:10.1107/S1600536812000050

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o441

doi:10.1107/S1600536812000050

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Ethyl 2-(4-carboxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate–N,N-dimethylformamide (1/1)

Noor Afshan Banu ^a and V. Bheema Raju ^b ^*

^aDepartment of Chemistry, KNS Institute of Technology, Bangalore 560 064, India, and ^bDepartment of Chemistry, Dr. Ambedkar Institute of Technology, Bangalore 560 056, India
^*Correspondence e-mail: 'bheemarajuv54@gmail.com

(Received 10 December 2011; accepted 1 January 2012; online 18 January 2012)

In the title compound, C₂₄H₂₀N₂O₅S·C₃H₇NO, a benzene ring is positioned axially to the pyrimidine ring, which adopts a twist-boat conformation, and is inclined to its mean plane by 85.36 (7)°. In the crystal, intermolecular C—H⋯O interactions result in centrosymmetric head-to-head dimers with an R₂²(14) graph-set motif along the b axis. Pairs of C—H⋯O and O—H⋯O hydrogen bonds form centrosymmetric head-to-head dimers about inversion centres, corresponding to an R₂²(7) graph-set motif along the a axis.

Related literature

For pharmacological properties of pyrimidine derivatives and general background, see: Alam et al. (2010 ). For a related structure, see: Jotani et al. (2010 ). For graph-set motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₅S·C₃H₇NO
M_r = 521.58
Triclinic, $[P \overline 1]$
a = 8.4146 (4) Å
b = 12.0699 (5) Å
c = 14.0185 (6) Å
α = 71.799 (2)°
β = 78.753 (2)°
γ = 86.488 (2)°
V = 1326.56 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.967, T_max = 0.975
23685 measured reflections
5788 independent reflections
3560 reflections with I > 2σ(I)'
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.178
S = 1.04
5788 reflections
339 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C81—H81⋯O5ⁱ	0.93	2.32	3.053 (3)	135
O4—H4⋯O11ⁱⁱ	0.82	1.81	2.618 (3)	170
C17—H17⋯O3ⁱⁱⁱ	0.93	2.43	3.310 (3)	157
Symmetry codes: (i) x-1, y+1, z; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000050/pv2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000050/pv2495Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000050/pv2495Isup3.cml

checkCIF report

Comment top

Pyrimidine derivatives are of interest because of their pharmacological properties (Alam et al., 2010). In the title molecule (Fig. 1), the central pyrimidine ring with a chiral C5 atom is significantly puckered and adopts a conformation which is best described as an intermediate between a boat and a screw boat form as reported in a closely related structure (Jotani et al., 2010). The ring puckering parameters (Cremer & Pople, 1975) for the pyrimidine ring are Q(2) = 0.1985 (2) Å, ϕ(2) = 159.70 (7)° and θ= 70.74 (6)°. A mean planes calculation shows that the atoms C5 and N1 deviate from the mean plane of the remaining ring atoms (N2/C4/C6/C7) by -0.1442 (2) and -0.0949 (2) Å, respectively, indicating that the conformation of the ring is that of a twisted boat. In the molecule, the fused thiazolopyrimidine and the benzene ring (C19—C24) are almost orthogonal with the dihedral angle between these rings being 85.36 (7)°. In the crystal, the carbonyl O3 atom is involved in a hydrogen bonding interaction C17—H17···O3 forming centrosymmetric dimers with R²₂(14) graph-set motif (Bernstein et al., 1995) along the b-axis. Pairs of C81—H81···O5 and O4—H4···O11 intermolecular interections generate centrosymmetric head-to-head dimers about inversion centres, corresponding to an R²₂(7) graph-set motif along the a- axis.

Related literature top

For pharmacological properties of pyrimidine derivatives and general background, see: Alam et al. (2010). For a related structure, see: Jotani et al. (2010). For graph-set motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 5-phenyl-6-methyl-2-thioxo-1,2,3,4-tetrahydro -pyrimidine-5-carboxylic acid ethyl ester (0.01 mol), chloroacetic acid (0.01 mol), 4-carboxy benzaldehyde (0.01 mol) and sodium acetate (1.5 g) in a mixture of glacial acetic acid and acetic anhydride (25 ml, 1:1) was refluxed for 8–10 h. The reaction mixture was concentrated and the solid thus obtained was filtered and recrystallized from ethyl acetate to get the title compound (78% yield, m.p. 427–428 K). The compound was recrystallized by slow evaporation of ethyl acetate-ethanol (6:4) solution, yielding pale yellow single crystals suitable for X-ray diffraction.

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

	Fig. 1. ORTEP (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines.

Ethyl 2-(4-carboxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H- thiazolo[3,2-a]pyrimidine-6-carboxylate–N,N- dimethylformamide (1/1) top

Crystal data top

C₂₄H₂₀N₂O₅S·C₃H₇NO	Z = 2
M_r = 521.58	F(000) = 548
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4146 (4) Å	Cell parameters from 5788 reflections
b = 12.0699 (5) Å	θ = 1.6–27.0°
c = 14.0185 (6) Å	µ = 0.17 mm⁻¹
α = 71.799 (2)°	T = 296 K
β = 78.753 (2)°	Block, yellow
γ = 86.488 (2)°	0.20 × 0.20 × 0.15 mm
V = 1326.56 (10) Å³

Data collection top

Bruker SMART APEX CCD detector diffractometer	5788 independent reflections
Radiation source: fine-focus sealed tube	3560 reflections with I > 2σ(I)'
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→8
T_min = 0.967, T_max = 0.975	k = −15→14
23685 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.103P)²] where P = (F_o² + 2F_c²)/3
5788 reflections	(Δ/σ)_max < 0.001
339 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₅S·C₃H₇NO	γ = 86.488 (2)°
M_r = 521.58	V = 1326.56 (10) Å³
Triclinic, P1	Z = 2
a = 8.4146 (4) Å	Mo Kα radiation
b = 12.0699 (5) Å	µ = 0.17 mm⁻¹
c = 14.0185 (6) Å	T = 296 K
α = 71.799 (2)°	0.20 × 0.20 × 0.15 mm
β = 78.753 (2)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	5788 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3560 reflections with I > 2σ(I)'
T_min = 0.967, T_max = 0.975	R_int = 0.033
23685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
5788 reflections	Δρ_min = −0.29 e Å⁻³
339 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
N22	0.6187 (3)	0.93566 (19)	0.32137 (16)	0.0806 (6)
C81	0.4744 (4)	0.9872 (3)	0.3273 (2)	0.0860 (8)
H81	0.4495	1.0414	0.2685	0.103*
C82	0.7324 (4)	0.9640 (3)	0.2250 (2)	0.1124 (11)
H82A	0.6825	1.0170	0.1725	0.169*
H82B	0.7631	0.8939	0.2074	0.169*
H82C	0.8270	0.9997	0.2315	0.169*
C83	0.6722 (5)	0.8554 (3)	0.4099 (3)	0.1303 (14)
H83A	0.6222	0.8755	0.4699	0.195*
H83B	0.7878	0.8600	0.4014	0.195*
H83C	0.6420	0.7774	0.4170	0.195*
O11	0.3700 (2)	0.96682 (18)	0.40786 (15)	0.1004 (6)
S1	0.30622 (7)	0.34995 (5)	0.35943 (4)	0.0618 (2)
N1	0.1227 (2)	0.48407 (14)	0.24302 (12)	0.0505 (4)
N2	0.0013 (2)	0.40960 (16)	0.41686 (12)	0.0610 (5)
O1	−0.29300 (18)	0.64562 (14)	0.17146 (12)	0.0718 (5)
O2	−0.4299 (2)	0.5986 (2)	0.33005 (16)	0.1173 (8)
O3	0.27644 (19)	0.52114 (14)	0.08332 (11)	0.0702 (5)
O5	1.2299 (2)	0.16084 (16)	0.22813 (13)	0.0837 (5)
O4	1.0939 (2)	0.07417 (16)	0.38392 (13)	0.0839 (5)
H4	1.1835	0.0469	0.3928	0.126*
C1	0.5294 (3)	0.38515 (19)	0.17748 (16)	0.0588 (6)
H1	0.5440	0.4212	0.1073	0.071*
C2	0.3822 (3)	0.40097 (18)	0.22858 (15)	0.0538 (5)
C3	0.2609 (3)	0.47380 (18)	0.17423 (15)	0.0536 (5)
C4	0.1213 (3)	0.42052 (18)	0.34338 (15)	0.0527 (5)
C5	−0.0051 (2)	0.56909 (17)	0.21469 (15)	0.0514 (5)
H5	−0.0318	0.5646	0.1510	0.062*
C6	−0.1543 (3)	0.53676 (19)	0.29785 (16)	0.0562 (5)
C7	−0.1450 (3)	0.46191 (19)	0.39185 (15)	0.0579 (6)
C8	−0.2833 (3)	0.4227 (2)	0.47932 (17)	0.0775 (7)
H8A	−0.2833	0.4658	0.5264	0.116*
H8B	−0.2722	0.3410	0.5135	0.116*
H8C	−0.3834	0.4361	0.4543	0.116*
C9	−0.3069 (3)	0.5942 (2)	0.27206 (18)	0.0668 (6)
C10	−0.4341 (3)	0.7095 (2)	0.1380 (2)	0.0848 (8)
H10A	−0.4629	0.7697	0.1708	0.102*
H10B	−0.5257	0.6572	0.1556	0.102*
C11	−0.3925 (5)	0.7620 (4)	0.0270 (3)	0.1493 (17)
H11A	−0.2973	0.8093	0.0103	0.224*
H11B	−0.4809	0.8097	0.0030	0.224*
H11C	−0.3721	0.7015	−0.0049	0.224*
C12	0.6698 (3)	0.32199 (18)	0.21211 (15)	0.0565 (5)
C13	0.6715 (3)	0.2478 (2)	0.31156 (17)	0.0687 (6)
H13	0.5766	0.2368	0.3602	0.082*
C14	0.8092 (3)	0.1918 (2)	0.33831 (17)	0.0662 (6)
H14	0.8070	0.1426	0.4045	0.079*
C15	0.9529 (3)	0.20750 (18)	0.26740 (16)	0.0575 (5)
C16	0.9541 (3)	0.2815 (2)	0.16903 (16)	0.0626 (6)
H16	1.0498	0.2931	0.1210	0.075*
C17	0.8164 (3)	0.3372 (2)	0.14224 (16)	0.0631 (6)
H17	0.8198	0.3865	0.0760	0.076*
C18	1.1052 (3)	0.1454 (2)	0.29103 (18)	0.0642 (6)
C19	0.0875 (3)	0.7233 (2)	0.2777 (2)	0.0732 (7)
H19	0.0673	0.6714	0.3436	0.088*
C20	0.1494 (4)	0.8341 (2)	0.2594 (3)	0.0925 (9)
H20	0.1719	0.8557	0.3136	0.111*
C21	0.1769 (3)	0.9101 (3)	0.1647 (3)	0.0941 (9)
H21	0.2184	0.9836	0.1536	0.113*
C22	0.1446 (4)	0.8801 (2)	0.0860 (3)	0.0948 (9)
H22	0.1636	0.9335	0.0207	0.114*
C23	0.0835 (3)	0.7708 (2)	0.10042 (18)	0.0736 (7)
H123	0.0609	0.7513	0.0453	0.088*
C24	0.0565 (2)	0.69169 (18)	0.19627 (16)	0.0563 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N22	0.0713 (15)	0.0885 (15)	0.0760 (14)	0.0075 (11)	−0.0098 (11)	−0.0205 (12)
C81	0.0765 (19)	0.099 (2)	0.0758 (18)	0.0023 (16)	−0.0131 (15)	−0.0185 (15)
C82	0.096 (2)	0.136 (3)	0.093 (2)	−0.003 (2)	0.0108 (18)	−0.035 (2)
C83	0.138 (3)	0.138 (3)	0.092 (2)	0.052 (2)	−0.030 (2)	−0.007 (2)
O11	0.0815 (14)	0.1229 (17)	0.0802 (13)	0.0172 (11)	−0.0075 (11)	−0.0152 (11)
S1	0.0619 (4)	0.0721 (4)	0.0442 (3)	0.0072 (3)	−0.0036 (2)	−0.0126 (3)
N1	0.0504 (10)	0.0541 (10)	0.0437 (9)	0.0008 (8)	−0.0037 (7)	−0.0136 (7)
N2	0.0576 (12)	0.0769 (13)	0.0442 (10)	−0.0033 (9)	0.0006 (8)	−0.0182 (9)
O1	0.0460 (9)	0.0916 (12)	0.0690 (10)	0.0024 (8)	−0.0089 (7)	−0.0137 (8)
O2	0.0598 (12)	0.172 (2)	0.0863 (13)	0.0252 (12)	0.0123 (10)	−0.0116 (13)
O3	0.0627 (10)	0.0922 (12)	0.0420 (8)	0.0120 (8)	0.0000 (7)	−0.0091 (8)
O5	0.0639 (11)	0.1041 (14)	0.0731 (11)	0.0089 (9)	−0.0061 (9)	−0.0185 (9)
O4	0.0758 (12)	0.0851 (12)	0.0725 (11)	0.0157 (10)	−0.0111 (9)	−0.0025 (9)
C1	0.0627 (14)	0.0618 (13)	0.0480 (11)	0.0066 (10)	−0.0040 (10)	−0.0163 (10)
C2	0.0579 (13)	0.0552 (12)	0.0446 (11)	0.0009 (10)	−0.0025 (9)	−0.0144 (9)
C3	0.0528 (12)	0.0596 (13)	0.0449 (11)	0.0011 (9)	−0.0006 (9)	−0.0167 (10)
C4	0.0566 (13)	0.0578 (13)	0.0428 (11)	−0.0036 (10)	−0.0052 (9)	−0.0162 (9)
C5	0.0454 (11)	0.0616 (13)	0.0460 (10)	−0.0023 (9)	−0.0043 (9)	−0.0170 (9)
C6	0.0476 (12)	0.0684 (14)	0.0536 (12)	−0.0072 (10)	−0.0014 (9)	−0.0234 (11)
C7	0.0493 (13)	0.0750 (15)	0.0512 (12)	−0.0068 (10)	−0.0005 (9)	−0.0260 (11)
C8	0.0581 (15)	0.111 (2)	0.0544 (13)	−0.0087 (13)	0.0049 (11)	−0.0200 (13)
C9	0.0487 (13)	0.0808 (16)	0.0644 (14)	−0.0059 (11)	−0.0017 (11)	−0.0171 (12)
C10	0.0514 (15)	0.0922 (19)	0.099 (2)	0.0032 (13)	−0.0153 (13)	−0.0124 (16)
C11	0.096 (3)	0.213 (4)	0.095 (2)	0.045 (3)	−0.021 (2)	0.009 (3)
C12	0.0574 (13)	0.0597 (13)	0.0496 (11)	0.0056 (10)	−0.0006 (10)	−0.0197 (10)
C13	0.0628 (15)	0.0707 (15)	0.0581 (13)	0.0114 (11)	0.0076 (11)	−0.0127 (11)
C14	0.0710 (16)	0.0635 (14)	0.0541 (13)	0.0105 (11)	−0.0035 (11)	−0.0111 (11)
C15	0.0604 (14)	0.0545 (13)	0.0604 (13)	0.0045 (10)	−0.0100 (10)	−0.0232 (10)
C16	0.0619 (14)	0.0734 (15)	0.0491 (12)	0.0004 (11)	0.0002 (10)	−0.0205 (11)
C17	0.0643 (15)	0.0748 (15)	0.0456 (11)	0.0054 (11)	−0.0046 (10)	−0.0161 (10)
C18	0.0657 (16)	0.0651 (15)	0.0643 (14)	0.0028 (11)	−0.0126 (12)	−0.0238 (12)
C19	0.0745 (17)	0.0701 (16)	0.0810 (17)	−0.0003 (12)	−0.0282 (13)	−0.0235 (13)
C20	0.094 (2)	0.0787 (19)	0.121 (3)	−0.0065 (16)	−0.0330 (19)	−0.0448 (19)
C21	0.079 (2)	0.0646 (18)	0.132 (3)	−0.0110 (14)	0.0014 (18)	−0.0317 (19)
C22	0.101 (2)	0.0659 (18)	0.091 (2)	−0.0015 (15)	0.0207 (17)	−0.0094 (15)
C23	0.0810 (17)	0.0666 (16)	0.0605 (14)	−0.0029 (13)	0.0094 (12)	−0.0148 (12)
C24	0.0385 (11)	0.0596 (13)	0.0665 (13)	0.0034 (9)	−0.0004 (9)	−0.0197 (11)

Geometric parameters (Å, º) top

N22—C81	1.330 (3)	C6—C9	1.475 (3)
N22—C83	1.447 (3)	C7—C8	1.493 (3)
N22—C82	1.450 (3)	C8—H8A	0.9600
C81—O11	1.254 (3)	C8—H8B	0.9600
C81—H81	0.9300	C8—H8C	0.9600
C82—H82A	0.9600	C10—C11	1.463 (4)
C82—H82B	0.9600	C10—H10A	0.9700
C82—H82C	0.9600	C10—H10B	0.9700
C83—H83A	0.9600	C11—H11A	0.9600
C83—H83B	0.9600	C11—H11B	0.9600
C83—H83C	0.9600	C11—H11C	0.9600
S1—C2	1.743 (2)	C12—C17	1.399 (3)
S1—C4	1.747 (2)	C12—C13	1.404 (3)
N1—C4	1.374 (2)	C13—C14	1.363 (3)
N1—C3	1.384 (2)	C13—H13	0.9300
N1—C5	1.464 (3)	C14—C15	1.388 (3)
N2—C4	1.274 (3)	C14—H14	0.9300
N2—C7	1.404 (3)	C15—C16	1.388 (3)
O1—C9	1.336 (3)	C15—C18	1.486 (3)
O1—C10	1.451 (3)	C16—C17	1.362 (3)
O2—C9	1.194 (3)	C16—H16	0.9300
O3—C3	1.207 (2)	C17—H17	0.9300
O5—C18	1.214 (3)	C19—C24	1.384 (3)
O4—C18	1.306 (3)	C19—C20	1.395 (3)
O4—H4	0.8200	C19—H19	0.9300
C1—C2	1.339 (3)	C20—C21	1.343 (4)
C1—C12	1.447 (3)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.342 (4)
C2—C3	1.473 (3)	C21—H21	0.9300
C5—C6	1.514 (3)	C22—C23	1.387 (4)
C5—C24	1.526 (3)	C22—H22	0.9300
C5—H5	0.9800	C23—C24	1.369 (3)
C6—C7	1.359 (3)	C23—H123	0.9300

C81—N22—C83	122.3 (3)	O2—C9—O1	121.6 (2)
C81—N22—C82	120.1 (2)	O2—C9—C6	127.1 (2)
C83—N22—C82	117.5 (3)	O1—C9—C6	111.30 (19)
O11—C81—N22	123.6 (3)	O1—C10—C11	107.4 (2)
O11—C81—H81	118.2	O1—C10—H10A	110.2
N22—C81—H81	118.2	C11—C10—H10A	110.2
N22—C82—H82A	109.5	O1—C10—H10B	110.2
N22—C82—H82B	109.5	C11—C10—H10B	110.2
H82A—C82—H82B	109.5	H10A—C10—H10B	108.5
N22—C82—H82C	109.5	C10—C11—H11A	109.5
H82A—C82—H82C	109.5	C10—C11—H11B	109.5
H82B—C82—H82C	109.5	H11A—C11—H11B	109.5
N22—C83—H83A	109.5	C10—C11—H11C	109.5
N22—C83—H83B	109.5	H11A—C11—H11C	109.5
H83A—C83—H83B	109.5	H11B—C11—H11C	109.5
N22—C83—H83C	109.5	C17—C12—C13	117.0 (2)
H83A—C83—H83C	109.5	C17—C12—C1	117.96 (19)
H83B—C83—H83C	109.5	C13—C12—C1	125.00 (19)
C2—S1—C4	91.62 (10)	C14—C13—C12	121.4 (2)
C4—N1—C3	115.96 (18)	C14—C13—H13	119.3
C4—N1—C5	120.81 (16)	C12—C13—H13	119.3
C3—N1—C5	122.69 (16)	C13—C14—C15	120.5 (2)
C4—N2—C7	116.87 (17)	C13—C14—H14	119.8
C9—O1—C10	115.94 (19)	C15—C14—H14	119.8
C18—O4—H4	109.5	C16—C15—C14	119.0 (2)
C2—C1—C12	131.4 (2)	C16—C15—C18	118.1 (2)
C2—C1—H1	114.3	C14—C15—C18	122.9 (2)
C12—C1—H1	114.3	C17—C16—C15	120.5 (2)
C1—C2—C3	120.46 (19)	C17—C16—H16	119.7
C1—C2—S1	128.94 (18)	C15—C16—H16	119.7
C3—C2—S1	110.56 (14)	C16—C17—C12	121.5 (2)
O3—C3—N1	123.1 (2)	C16—C17—H17	119.2
O3—C3—C2	126.56 (19)	C12—C17—H17	119.2
N1—C3—C2	110.27 (17)	O5—C18—O4	123.2 (2)
N2—C4—N1	125.9 (2)	O5—C18—C15	121.9 (2)
N2—C4—S1	122.68 (16)	O4—C18—C15	114.9 (2)
N1—C4—S1	111.41 (15)	C24—C19—C20	119.0 (3)
N1—C5—C6	108.64 (16)	C24—C19—H19	120.5
N1—C5—C24	109.51 (16)	C20—C19—H19	120.5
C6—C5—C24	113.05 (16)	C21—C20—C19	120.8 (3)
N1—C5—H5	108.5	C21—C20—H20	119.6
C6—C5—H5	108.5	C19—C20—H20	119.6
C24—C5—H5	108.5	C22—C21—C20	120.2 (3)
C7—C6—C9	122.49 (19)	C22—C21—H21	119.9
C7—C6—C5	121.1 (2)	C20—C21—H21	119.9
C9—C6—C5	116.33 (19)	C21—C22—C23	121.0 (3)
C6—C7—N2	122.32 (18)	C21—C22—H22	119.5
C6—C7—C8	126.0 (2)	C23—C22—H22	119.5
N2—C7—C8	111.64 (19)	C24—C23—C22	119.6 (3)
C7—C8—H8A	109.5	C24—C23—H123	120.2
C7—C8—H8B	109.5	C22—C23—H123	120.2
H8A—C8—H8B	109.5	C23—C24—C19	119.3 (2)
C7—C8—H8C	109.5	C23—C24—C5	121.2 (2)
H8A—C8—H8C	109.5	C19—C24—C5	119.48 (19)
H8B—C8—H8C	109.5

C83—N22—C81—O11	−3.7 (5)	C10—O1—C9—O2	1.9 (4)
C82—N22—C81—O11	179.8 (3)	C10—O1—C9—C6	−177.28 (19)
C12—C1—C2—C3	177.9 (2)	C7—C6—C9—O2	12.6 (4)
C12—C1—C2—S1	0.5 (4)	C5—C6—C9—O2	−165.1 (3)
C4—S1—C2—C1	178.1 (2)	C7—C6—C9—O1	−168.28 (19)
C4—S1—C2—C3	0.47 (15)	C5—C6—C9—O1	14.0 (3)
C4—N1—C3—O3	177.18 (19)	C9—O1—C10—C11	178.0 (3)
C5—N1—C3—O3	−11.1 (3)	C2—C1—C12—C17	−169.5 (2)
C4—N1—C3—C2	−4.2 (2)	C2—C1—C12—C13	9.1 (4)
C5—N1—C3—C2	167.44 (16)	C17—C12—C13—C14	−1.0 (4)
C1—C2—C3—O3	2.6 (3)	C1—C12—C13—C14	−179.7 (2)
S1—C2—C3—O3	−179.55 (19)	C12—C13—C14—C15	0.5 (4)
C1—C2—C3—N1	−175.93 (19)	C13—C14—C15—C16	0.2 (4)
S1—C2—C3—N1	1.9 (2)	C13—C14—C15—C18	−177.7 (2)
C7—N2—C4—N1	3.8 (3)	C14—C15—C16—C17	−0.4 (3)
C7—N2—C4—S1	−174.05 (14)	C18—C15—C16—C17	177.6 (2)
C3—N1—C4—N2	−173.4 (2)	C15—C16—C17—C12	−0.1 (4)
C5—N1—C4—N2	14.7 (3)	C13—C12—C17—C16	0.8 (3)
C3—N1—C4—S1	4.6 (2)	C1—C12—C17—C16	179.59 (19)
C5—N1—C4—S1	−167.20 (14)	C16—C15—C18—O5	2.5 (3)
C2—S1—C4—N2	175.35 (19)	C14—C15—C18—O5	−179.6 (2)
C2—S1—C4—N1	−2.79 (15)	C16—C15—C18—O4	−177.68 (19)
C4—N1—C5—C6	−23.1 (2)	C14—C15—C18—O4	0.2 (3)
C3—N1—C5—C6	165.58 (17)	C24—C19—C20—C21	0.9 (4)
C4—N1—C5—C24	100.8 (2)	C19—C20—C21—C22	0.1 (5)
C3—N1—C5—C24	−70.5 (2)	C20—C21—C22—C23	−0.3 (5)
N1—C5—C6—C7	16.6 (3)	C21—C22—C23—C24	−0.5 (4)
C24—C5—C6—C7	−105.2 (2)	C22—C23—C24—C19	1.5 (4)
N1—C5—C6—C9	−165.65 (17)	C22—C23—C24—C5	−177.9 (2)
C24—C5—C6—C9	72.6 (2)	C20—C19—C24—C23	−1.6 (4)
C9—C6—C7—N2	−178.39 (19)	C20—C19—C24—C5	177.7 (2)
C5—C6—C7—N2	−0.8 (3)	N1—C5—C24—C23	111.4 (2)
C9—C6—C7—C8	3.0 (4)	C6—C5—C24—C23	−127.4 (2)
C5—C6—C7—C8	−179.4 (2)	N1—C5—C24—C19	−67.9 (2)
C4—N2—C7—C6	−10.7 (3)	C6—C5—C24—C19	53.3 (3)
C4—N2—C7—C8	168.12 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C81—H81···O5ⁱ	0.93	2.32	3.053 (3)	135
O4—H4···O11ⁱⁱ	0.82	1.81	2.618 (3)	170
C17—H17···O3ⁱⁱⁱ	0.93	2.43	3.310 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₅S·C₃H₇NO
M_r	521.58
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.4146 (4), 12.0699 (5), 14.0185 (6)
α, β, γ (°)	71.799 (2), 78.753 (2), 86.488 (2)
V (Å³)	1326.56 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.967, 0.975
No. of measured, independent and observed [I > 2σ(I)'] reflections	23685, 5788, 3560
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.178, 1.04
No. of reflections	5788
No. of parameters	339
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

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

D—H···A	D—H	H···A	D···A	D—H···A
C81—H81···O5ⁱ	0.930	2.320	3.053 (3)	135
O4—H4···O11ⁱⁱ	0.820	1.805	2.618 (3)	170
C17—H17···O3ⁱⁱⁱ	0.930	2.434	3.310 (3)	157

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

Acknowledgements

NAB is thankful to the KNS Institute of Technology for all the encouragement.

References

Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245–1258. Web of Science CrossRef CAS Google Scholar
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. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jotani, M. M., Baldaniya, B. B. & Jasinski, J. P. (2010). Acta Cryst. E66, o599–o600. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England Google Scholar

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

Ethyl 2-(4-carb­­oxy­benzyl­­idene)-7-methyl-3-oxo-5-phenyl-2,3-di­hydro-5H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate–N,N-di­methyl­formamide (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-(4-carboxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate–N,N-dimethylformamide (1/1)