5′-Methyl­sulfanyl-4′-oxo-7′-phenyl-3′,4′-dihydro-1′H-spiro­[cyclo­hexane-1,2′-quinazoline]-8′-carbonitrile dimethyl­formamide monosolvate

Liu, X.; Shi, D.; Tang, J.; Yang, D.; Li, J.

doi:10.1107/S1600536811026948

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2016

doi:10.1107/S1600536811026948

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5′-Methylsulfanyl-4′-oxo-7′-phenyl-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-quinazoline]-8′-carbonitrile dimethylformamide monosolvate

Xuan Liu,^a Daxin Shi,^a Jianhong Tang,^a,^b Deli Yang ^a and Jiarong Li ^a ^*

^aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, and ^bCollege of Chemical Engineering, Huaqiao University, Xiamen Fujian 362021, People's Republic of China
^*Correspondence e-mail: jrli@bit.edu.cn

(Received 20 May 2011; accepted 6 July 2011; online 13 July 2011)

In the title compound, C₂₁H₂₁N₃OS·C₃H₇NO, the carbonitrile molecule is built up of two fused six-membered rings and one six-membered ring linked through a spiro C atom. The 1,3-diaza ring adopts an envelope conformation and the cyclohexane ring adopts a chair conformation. The dihedral angle between the aromatic rings is 46.7 (3)°. In the crystal, the components are linked by N—H⋯O hydrogen bonds.

Related literature

For medicinal and biological properties of dihydroquinazolin-3H-4-one derivatives, see: Alagarsamy & Murugesan (2007 ); Wang et al. (2007 ); Jatav et al. (2008 ); Markosyan et al. (2010 ). For a related structure, see Zhang et al. (2008 ).

Experimental

Crystal data

C₂₁H₂₁N₃OS·C₃H₇NO
M_r = 436.56
Triclinic, $[P \overline 1]$
a = 9.415 (3) Å
b = 10.615 (3) Å
c = 12.037 (3) Å
α = 95.092 (3)°
β = 98.156 (4)°
γ = 109.833 (3)°
V = 1108.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 153 K
0.31 × 0.31 × 0.12 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.947, T_max = 0.979
11758 measured reflections
5754 independent reflections
4274 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.117
S = 1.00
5754 reflections
291 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N3ⁱ	0.838 (10)	2.328 (14)	3.120 (2)	157.96 (3)
N2—H21⋯O1ⁱⁱ	0.886 (10)	2.044 (18)	2.927 (3)	174.94 (3)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026948/aa2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026948/aa2012Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026948/aa2012Isup3.cml

checkCIF report

Comment top

The molecular structure of 5'-methylthio-4'-oxo-7'-phenyl-3',4'-dihydro-1'H-spiro[cyclohexane-1, 2'-quinazoline]-8'-carbonitrile(I) is built up with one six membered ring and two fused six membered rings and a six membered ring linked through a spiro C atom (Fig. 1). The ring of C1, C2, C3, C4, C5, C6 exists in an chair conformation, and the C6 atom displaced by 0.647 (6)Å from the ring of C1, C2, C4, C5 (planar within 0.019 (5) Å), while C3 atom displaced by 0.669 (8) Å. The 1,3-diaza ring exists in an envelope conformation, and the C6 atom displaced by 0.476 (5)Å from the rest of the atoms of the 1,3-diaza ring (planar within 0.013 (5) Å). The dihedral angle between the plane (C14, C15, C16, C17, C18, C19) and the plane (C8, C9, C10, C11, C12, C13) is 46.7 (3)°. The angle between C9, S1, C20 is 102.83 (8) Å. The geometry of the fused rings compares well with the related spiro[cyclopentane-1,2'(1'H)-quinazolin]-4'(3'H)-one] (Zhang et al., 2008). The crystal packing is stabilized by intermolecular N—H···O and N—H···N bonds.

Related literature top

For medicinal and biological properities of dihydroquinazolin-3H-4-one derivatives, see: Alagarsamy & Murugesan (2007); Wang et al. (2007); Jatav et al. (2008); Markosyan et al. (2010). For a related structure, see Zhang et al. (2008).

Experimental top

To a solution of cyclohexanone (3 ml) and sodium hydroxide (0.3 mmol) were added 3-amino-5-(methylthio)biphenyl-2,4-dicarbonitrile (0.1 mmol). The mixture was heated at 373 K for 2.0 h. The reaction mixture was cooled with ice water (20 ml) and then filtered to give the title compound. The product was recrystallizated from a mixed solvent (ethanol:N,N-dimethylformamide 1:3) to obtain colorless single crystals. M.p. 572–573 K. Spectra data: IR (KBr): 3317, 3219, 2933, 2216, 1650, 1585, 1550, 1413, 771, 709 cm^-1. ¹H-NMR (DMSO-d₆, p.p.m.): 0.92–1.84 (10H, m, C₅H₁₀), 2.38 (3H, s, SCH₃), 6.50(1H, s, NH), 6.61 (1H, s, ArH), 7.50–7.61 (5H, m, ArH), 8.29 (1H, s, NH). ESI-MS m/z: [M+H]⁺ 364.1. C₂₁H₂₁N₃OS: calcd. % C 69.39, H 5.82, N 11.56; found % C 69.28, H 5.68, N 11.31.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids
	Fig. 2. The crystal structure of (I), viewed along a axis

5'-Methylsulfanyl-4'-oxo-7'-phenyl-3',4'-dihydro-1'H- spiro[cyclohexane-1,2'-quinazoline]-8'-carbonitrile dimethylformamide monosolvate top

Crystal data top

C₂₁H₂₁N₃OS·C₃H₇NO	Z = 2
M_r = 436.56	F(000) = 464
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.415 (3) Å	Cell parameters from 3507 reflections
b = 10.615 (3) Å	θ = 2.5–29.1°
c = 12.037 (3) Å	µ = 0.18 mm⁻¹
α = 95.092 (3)°	T = 153 K
β = 98.156 (4)°	Chunk, colorless
γ = 109.833 (3)°	0.31 × 0.31 × 0.12 mm
V = 1108.0 (6) Å³

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	5754 independent reflections
Radiation source: Rotating Anode	4274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 28.5714 pixels mm^-1	θ_max = 29.1°, θ_min = 2.5°
phi and ω scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→14
T_min = 0.947, T_max = 0.979	l = −16→15
11758 measured reflections

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) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0568P)² + 0.160P] where P = (F_o² + 2F_c²)/3
5754 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₂₁N₃OS·C₃H₇NO	γ = 109.833 (3)°
M_r = 436.56	V = 1108.0 (6) Å³
Triclinic, P1	Z = 2
a = 9.415 (3) Å	Mo Kα radiation
b = 10.615 (3) Å	µ = 0.18 mm⁻¹
c = 12.037 (3) Å	T = 153 K
α = 95.092 (3)°	0.31 × 0.31 × 0.12 mm
β = 98.156 (4)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	5754 independent reflections
Absorption correction: ψ scan (North et al., 1968)	4274 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.979	R_int = 0.029
11758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.36 e Å⁻³
5754 reflections	Δρ_min = −0.26 e Å⁻³
291 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 > 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
S1	0.30973 (5)	0.65929 (4)	0.27438 (3)	0.02075 (11)
O1	0.43889 (14)	0.57074 (13)	0.11197 (9)	0.0275 (3)
N4	0.75021 (19)	0.94951 (17)	0.28720 (14)	0.0374 (4)
O2	0.6020 (2)	1.02046 (18)	0.39412 (16)	0.0580 (5)
N1	0.79059 (16)	0.52496 (15)	0.31427 (11)	0.0197 (3)
N2	0.63848 (16)	0.49735 (14)	0.13547 (11)	0.0200 (3)
N3	0.99764 (17)	0.62325 (16)	0.58365 (11)	0.0259 (3)
C1	0.87655 (18)	0.44768 (18)	0.15077 (13)	0.0221 (3)
H1A	0.9264	0.5415	0.1362	0.026*
H1B	0.9511	0.4266	0.2057	0.026*
C2	0.8378 (2)	0.3509 (2)	0.03980 (14)	0.0288 (4)
H2A	0.7780	0.3812	−0.0195	0.035*
H2B	0.9341	0.3531	0.0145	0.035*
C3	0.7457 (2)	0.2069 (2)	0.05401 (16)	0.0362 (5)
H3A	0.8102	0.1724	0.1062	0.043*
H3B	0.7158	0.1481	−0.0204	0.043*
C4	0.6018 (2)	0.20061 (19)	0.10126 (16)	0.0316 (4)
H4A	0.5451	0.1063	0.1114	0.038*
H4B	0.5338	0.2292	0.0468	0.038*
C5	0.64463 (19)	0.29280 (17)	0.21494 (14)	0.0226 (3)
H5A	0.7069	0.2603	0.2707	0.027*
H5B	0.5499	0.2887	0.2436	0.027*
C6	0.73564 (17)	0.43950 (16)	0.20362 (12)	0.0166 (3)
C7	0.54013 (18)	0.54868 (16)	0.17623 (13)	0.0187 (3)
C8	0.56754 (17)	0.58920 (16)	0.30038 (12)	0.0163 (3)
C9	0.47755 (17)	0.65007 (16)	0.35316 (13)	0.0166 (3)
C10	0.52394 (17)	0.70489 (16)	0.46842 (13)	0.0178 (3)
H10	0.4628	0.7455	0.5037	0.021*
C11	0.65724 (17)	0.70114 (15)	0.53231 (13)	0.0165 (3)
C12	0.74383 (17)	0.63548 (16)	0.48131 (12)	0.0160 (3)
C13	0.69977 (17)	0.57954 (15)	0.36522 (13)	0.0160 (3)
C14	0.71051 (17)	0.77401 (16)	0.65038 (13)	0.0168 (3)
C15	0.70835 (19)	0.90471 (17)	0.67204 (14)	0.0222 (3)
H15	0.6717	0.9444	0.6119	0.027*
C16	0.7592 (2)	0.97693 (18)	0.78055 (14)	0.0276 (4)
H16	0.7583	1.0662	0.7942	0.033*
C17	0.8112 (2)	0.9198 (2)	0.86898 (14)	0.0303 (4)
H17	0.8468	0.9700	0.9431	0.036*
C18	0.8114 (2)	0.7890 (2)	0.84928 (14)	0.0282 (4)
H18	0.8453	0.7491	0.9103	0.034*
C19	0.76196 (19)	0.71616 (18)	0.74030 (13)	0.0218 (3)
H19	0.7632	0.6270	0.7270	0.026*
C20	0.2291 (2)	0.72814 (19)	0.38122 (15)	0.0271 (4)
H20A	0.2100	0.6684	0.4393	0.033*
H20B	0.1321	0.7352	0.3461	0.033*
H20C	0.3013	0.8182	0.4163	0.033*
C21	0.88385 (18)	0.63108 (16)	0.54123 (13)	0.0183 (3)
C22	0.6208 (3)	0.9699 (2)	0.3065 (2)	0.0446 (6)
H22	0.5366	0.9415	0.2448	0.053*
C24	0.8796 (3)	0.9892 (3)	0.3788 (2)	0.0567 (7)
H24A	0.8536	1.0275	0.4468	0.068*
H24B	0.9676	1.0573	0.3576	0.068*
H24C	0.9058	0.9099	0.3944	0.068*
C23	0.7636 (3)	0.8852 (3)	0.1816 (2)	0.0654 (8)
H23A	0.6646	0.8547	0.1295	0.078*
H23B	0.7935	0.8070	0.1947	0.078*
H23C	0.8418	0.9496	0.1485	0.078*
H11	0.855 (2)	0.504 (2)	0.3564 (16)	0.029 (5)*
H21	0.621 (2)	0.4760 (19)	0.0607 (17)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01842 (19)	0.0274 (2)	0.0198 (2)	0.01458 (16)	0.00019 (15)	0.00021 (16)
O1	0.0315 (7)	0.0441 (8)	0.0155 (6)	0.0282 (6)	−0.0021 (5)	−0.0003 (5)
N4	0.0314 (9)	0.0385 (10)	0.0354 (9)	0.0042 (7)	0.0027 (7)	0.0091 (8)
O2	0.0584 (11)	0.0559 (11)	0.0747 (12)	0.0312 (9)	0.0266 (10)	0.0201 (10)
N1	0.0200 (7)	0.0298 (8)	0.0127 (6)	0.0164 (6)	−0.0019 (5)	−0.0024 (6)
N2	0.0241 (7)	0.0299 (8)	0.0117 (7)	0.0179 (6)	0.0011 (5)	0.0016 (6)
N3	0.0253 (7)	0.0387 (9)	0.0182 (7)	0.0192 (7)	0.0016 (6)	−0.0002 (6)
C1	0.0196 (7)	0.0350 (10)	0.0168 (8)	0.0153 (7)	0.0048 (6)	0.0058 (7)
C2	0.0305 (9)	0.0491 (12)	0.0175 (8)	0.0277 (9)	0.0062 (7)	0.0020 (8)
C3	0.0482 (12)	0.0418 (12)	0.0254 (10)	0.0303 (10)	0.0008 (8)	−0.0086 (8)
C4	0.0362 (10)	0.0254 (10)	0.0309 (10)	0.0125 (8)	0.0003 (8)	−0.0041 (8)
C5	0.0231 (8)	0.0256 (9)	0.0215 (8)	0.0118 (7)	0.0042 (6)	0.0029 (7)
C6	0.0189 (7)	0.0239 (8)	0.0104 (7)	0.0130 (6)	0.0013 (6)	0.0006 (6)
C7	0.0210 (7)	0.0224 (8)	0.0156 (8)	0.0126 (6)	0.0016 (6)	0.0009 (6)
C8	0.0169 (7)	0.0198 (8)	0.0141 (7)	0.0095 (6)	0.0014 (6)	0.0013 (6)
C9	0.0155 (7)	0.0187 (8)	0.0163 (7)	0.0076 (6)	0.0014 (6)	0.0031 (6)
C10	0.0182 (7)	0.0215 (8)	0.0170 (8)	0.0112 (6)	0.0044 (6)	0.0015 (6)
C11	0.0172 (7)	0.0178 (8)	0.0154 (7)	0.0072 (6)	0.0036 (6)	0.0023 (6)
C12	0.0166 (7)	0.0185 (8)	0.0142 (7)	0.0087 (6)	0.0010 (6)	0.0015 (6)
C13	0.0167 (7)	0.0176 (8)	0.0158 (7)	0.0087 (6)	0.0032 (6)	0.0022 (6)
C14	0.0162 (7)	0.0209 (8)	0.0145 (7)	0.0083 (6)	0.0039 (6)	0.0006 (6)
C15	0.0251 (8)	0.0260 (9)	0.0182 (8)	0.0131 (7)	0.0042 (6)	0.0014 (7)
C16	0.0341 (10)	0.0251 (9)	0.0253 (9)	0.0147 (8)	0.0059 (7)	−0.0048 (7)
C17	0.0343 (10)	0.0404 (11)	0.0159 (8)	0.0176 (8)	0.0002 (7)	−0.0078 (7)
C18	0.0320 (9)	0.0418 (11)	0.0165 (8)	0.0213 (8)	0.0022 (7)	0.0046 (8)
C19	0.0248 (8)	0.0260 (9)	0.0189 (8)	0.0136 (7)	0.0063 (6)	0.0043 (7)
C20	0.0240 (8)	0.0369 (11)	0.0274 (9)	0.0203 (8)	0.0055 (7)	0.0013 (8)
C21	0.0229 (8)	0.0220 (8)	0.0121 (7)	0.0117 (6)	0.0032 (6)	−0.0017 (6)
C22	0.0348 (11)	0.0402 (13)	0.0534 (14)	0.0054 (9)	0.0004 (10)	0.0248 (11)
C24	0.0370 (12)	0.0674 (18)	0.0595 (16)	0.0165 (12)	−0.0021 (11)	0.0040 (13)
C23	0.079 (2)	0.0561 (17)	0.0461 (15)	0.0015 (14)	0.0222 (14)	0.0024 (12)

Geometric parameters (Å, º) top

S1—C9	1.7611 (16)	C8—C9	1.411 (2)
S1—C20	1.8033 (17)	C8—C13	1.412 (2)
O1—C7	1.2394 (18)	C9—C10	1.402 (2)
N4—C22	1.355 (3)	C10—C11	1.391 (2)
N4—C23	1.431 (3)	C10—H10	0.9500
N4—C24	1.437 (3)	C11—C12	1.407 (2)
O2—C22	1.204 (3)	C11—C14	1.486 (2)
N1—C13	1.3655 (19)	C12—C13	1.414 (2)
N1—C6	1.4616 (19)	C12—C21	1.428 (2)
N1—H11	0.84 (2)	C14—C15	1.396 (2)
N2—C7	1.349 (2)	C14—C19	1.398 (2)
N2—C6	1.4644 (19)	C15—C16	1.385 (2)
N2—H21	0.89 (2)	C15—H15	0.9500
N3—C21	1.152 (2)	C16—C17	1.381 (3)
C1—C2	1.529 (2)	C16—H16	0.9500
C1—C6	1.531 (2)	C17—C18	1.389 (3)
C1—H1A	0.9900	C17—H17	0.9500
C1—H1B	0.9900	C18—C19	1.392 (2)
C2—C3	1.519 (3)	C18—H18	0.9500
C2—H2A	0.9900	C19—H19	0.9500
C2—H2B	0.9900	C20—H20A	0.9800
C3—C4	1.525 (3)	C20—H20B	0.9800
C3—H3A	0.9900	C20—H20C	0.9800
C3—H3B	0.9900	C22—H22	0.9500
C4—C5	1.527 (2)	C24—H24A	0.9800
C4—H4A	0.9900	C24—H24B	0.9800
C4—H4B	0.9900	C24—H24C	0.9800
C5—C6	1.531 (2)	C23—H23A	0.9800
C5—H5A	0.9900	C23—H23B	0.9800
C5—H5B	0.9900	C23—H23C	0.9800
C7—C8	1.479 (2)

C9—S1—C20	102.83 (8)	C8—C9—S1	120.24 (11)
C22—N4—C23	123.6 (2)	C11—C10—C9	121.56 (14)
C22—N4—C24	118.59 (19)	C11—C10—H10	119.2
C23—N4—C24	117.7 (2)	C9—C10—H10	119.2
C13—N1—C6	122.09 (13)	C10—C11—C12	119.13 (14)
C13—N1—H11	117.5 (13)	C10—C11—C14	119.37 (13)
C6—N1—H11	112.7 (13)	C12—C11—C14	121.38 (14)
C7—N2—C6	124.20 (13)	C11—C12—C13	120.40 (14)
C7—N2—H21	114.8 (13)	C11—C12—C21	121.94 (14)
C6—N2—H21	118.3 (13)	C13—C12—C21	117.50 (13)
C2—C1—C6	113.17 (14)	N1—C13—C8	120.12 (13)
C2—C1—H1A	108.9	N1—C13—C12	120.04 (14)
C6—C1—H1A	108.9	C8—C13—C12	119.68 (13)
C2—C1—H1B	108.9	C15—C14—C19	118.98 (15)
C6—C1—H1B	108.9	C15—C14—C11	118.66 (14)
H1A—C1—H1B	107.8	C19—C14—C11	122.36 (14)
C3—C2—C1	111.36 (15)	C16—C15—C14	120.51 (16)
C3—C2—H2A	109.4	C16—C15—H15	119.7
C1—C2—H2A	109.4	C14—C15—H15	119.7
C3—C2—H2B	109.4	C17—C16—C15	120.32 (17)
C1—C2—H2B	109.4	C17—C16—H16	119.8
H2A—C2—H2B	108.0	C15—C16—H16	119.8
C2—C3—C4	111.08 (15)	C16—C17—C18	119.89 (16)
C2—C3—H3A	109.4	C16—C17—H17	120.1
C4—C3—H3A	109.4	C18—C17—H17	120.1
C2—C3—H3B	109.4	C17—C18—C19	120.19 (16)
C4—C3—H3B	109.4	C17—C18—H18	119.9
H3A—C3—H3B	108.0	C19—C18—H18	119.9
C3—C4—C5	110.48 (15)	C18—C19—C14	120.10 (16)
C3—C4—H4A	109.6	C18—C19—H19	120.0
C5—C4—H4A	109.6	C14—C19—H19	120.0
C3—C4—H4B	109.6	S1—C20—H20A	109.5
C5—C4—H4B	109.6	S1—C20—H20B	109.5
H4A—C4—H4B	108.1	H20A—C20—H20B	109.5
C4—C5—C6	111.32 (14)	S1—C20—H20C	109.5
C4—C5—H5A	109.4	H20A—C20—H20C	109.5
C6—C5—H5A	109.4	H20B—C20—H20C	109.5
C4—C5—H5B	109.4	N3—C21—C12	175.83 (16)
C6—C5—H5B	109.4	O2—C22—N4	126.4 (2)
H5A—C5—H5B	108.0	O2—C22—H22	116.8
N1—C6—N2	106.52 (12)	N4—C22—H22	116.8
N1—C6—C5	111.29 (13)	N4—C24—H24A	109.5
N2—C6—C5	110.69 (13)	N4—C24—H24B	109.5
N1—C6—C1	107.40 (13)	H24A—C24—H24B	109.5
N2—C6—C1	110.23 (13)	N4—C24—H24C	109.5
C5—C6—C1	110.60 (13)	H24A—C24—H24C	109.5
O1—C7—N2	121.46 (14)	H24B—C24—H24C	109.5
O1—C7—C8	121.36 (14)	N4—C23—H23A	109.5
N2—C7—C8	116.94 (14)	N4—C23—H23B	109.5
C9—C8—C13	119.62 (13)	H23A—C23—H23B	109.5
C9—C8—C7	122.55 (14)	N4—C23—H23C	109.5
C13—C8—C7	117.44 (13)	H23A—C23—H23C	109.5
C10—C9—C8	119.49 (14)	H23B—C23—H23C	109.5
C10—C9—S1	120.26 (11)

C6—C1—C2—C3	−52.6 (2)	C9—C10—C11—C12	−2.9 (2)
C1—C2—C3—C4	54.9 (2)	C9—C10—C11—C14	173.20 (14)
C2—C3—C4—C5	−57.9 (2)	C10—C11—C12—C13	2.9 (2)
C3—C4—C5—C6	58.0 (2)	C14—C11—C12—C13	−173.08 (14)
C13—N1—C6—N2	37.8 (2)	C10—C11—C12—C21	178.32 (14)
C13—N1—C6—C5	−82.94 (18)	C14—C11—C12—C21	2.3 (2)
C13—N1—C6—C1	155.88 (15)	C6—N1—C13—C8	−18.7 (2)
C7—N2—C6—N1	−39.4 (2)	C6—N1—C13—C12	165.86 (14)
C7—N2—C6—C5	81.73 (18)	C9—C8—C13—N1	−177.79 (14)
C7—N2—C6—C1	−155.59 (15)	C7—C8—C13—N1	−4.8 (2)
C4—C5—C6—N1	−173.96 (13)	C9—C8—C13—C12	−2.4 (2)
C4—C5—C6—N2	67.79 (16)	C7—C8—C13—C12	170.62 (14)
C4—C5—C6—C1	−54.67 (18)	C11—C12—C13—N1	175.10 (15)
C2—C1—C6—N1	173.76 (14)	C21—C12—C13—N1	−0.5 (2)
C2—C1—C6—N2	−70.58 (18)	C11—C12—C13—C8	−0.3 (2)
C2—C1—C6—C5	52.15 (18)	C21—C12—C13—C8	−175.91 (14)
C6—N2—C7—O1	−165.03 (15)	C10—C11—C14—C15	−44.1 (2)
C6—N2—C7—C8	20.5 (2)	C12—C11—C14—C15	131.86 (16)
O1—C7—C8—C9	2.4 (3)	C10—C11—C14—C19	135.62 (16)
N2—C7—C8—C9	176.94 (15)	C12—C11—C14—C19	−48.4 (2)
O1—C7—C8—C13	−170.34 (16)	C19—C14—C15—C16	1.2 (2)
N2—C7—C8—C13	4.2 (2)	C11—C14—C15—C16	−179.02 (15)
C13—C8—C9—C10	2.5 (2)	C14—C15—C16—C17	−0.7 (3)
C7—C8—C9—C10	−170.18 (14)	C15—C16—C17—C18	−0.5 (3)
C13—C8—C9—S1	−178.45 (12)	C16—C17—C18—C19	1.2 (3)
C7—C8—C9—S1	8.9 (2)	C17—C18—C19—C14	−0.6 (3)
C20—S1—C9—C10	−6.48 (15)	C15—C14—C19—C18	−0.6 (2)
C20—S1—C9—C8	174.42 (13)	C11—C14—C19—C18	179.68 (15)
C8—C9—C10—C11	0.2 (2)	C23—N4—C22—O2	178.2 (2)
S1—C9—C10—C11	−178.91 (12)	C24—N4—C22—O2	0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N3ⁱ	0.838 (10)	2.328 (14)	3.120 (2)	157.96 (3)
N2—H21···O1ⁱⁱ	0.886 (10)	2.044 (18)	2.927 (3)	174.94 (3)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃OS·C₃H₇NO
M_r	436.56
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	9.415 (3), 10.615 (3), 12.037 (3)
α, β, γ (°)	95.092 (3), 98.156 (4), 109.833 (3)
V (Å³)	1108.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.31 × 0.31 × 0.12

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.947, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	11758, 5754, 4274
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.117, 1.00
No. of reflections	5754
No. of parameters	291
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.26

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N3ⁱ	0.838 (10)	2.328 (14)	3.120 (2)	157.96 (3)
N2—H21···O1ⁱⁱ	0.886 (10)	2.044 (18)	2.927 (3)	174.94 (3)

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

Acknowledgements

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

References

Alagarsamy, V. & Murugesan, S. (2007). Chem. Pharm. Bull. 55, 76–80. Web of Science CrossRef PubMed CAS Google Scholar
Jatav, V., Kashaw, S. & Mishra, P. (2008). Med. Chem. Res. 17, 169–181. Web of Science CrossRef CAS Google Scholar
Markosyan, A. I., Dilanyan, S. V., Arsenyan, F. G., Sukasyan, R. S., Sarkisyan, I. S. & Garibdzhanyan, B. T. (2010). Pharm. Chem. J. 44, 111–114. CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, K., Kirichian, A. M., Al Aowad, A. F., Adelstein, S. J. & Kassis, A. I. (2007). Bioconjug. Chem. 18, 754–764. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, L., Li, J., Shi, D. & Chen, J. (2008). Acta Cryst. E64, o449. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

5′-Methyl­sulfanyl-4′-oxo-7′-phenyl-3′,4′-di­hydro-1′H-spiro­[cyclo­hexane-1,2′-quinazoline]-8′-carbo­nitrile di­methyl­formamide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5′-Methylsulfanyl-4′-oxo-7′-phenyl-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-quinazoline]-8′-carbonitrile dimethylformamide monosolvate