5'-Methyl-sulfanyl-4'-oxo-7'-phenyl-3',4'-dihydro-1'H-spiro-[cyclo-hexane-1,2'-quinazoline]-8'-carbonitrile dimethyl-formamide monosolvate.

In the title compound, C(21)H(21)N(3)OS·C(3)H(7)NO, the carbonitrile mol-ecule 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 cyclo-hexane 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 = 436.56

Triclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.117

S = 1.00

5754 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.26 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026948/aa2012sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811026948/aa2012Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21N3OS·C3H7NO	Z = 2
Mr = 436.56	F(000) = 464
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0568P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
5754 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .