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

Tang, J.; Shi, D.; Yan, L.; Liu, X.; Li, J.

doi:10.1107/S160053681102188X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1672

doi:10.1107/S160053681102188X

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

Jianhong Tang,^a,^b Daxin Shi,^a Liupan Yan,^a Xuan Liu ^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 17 May 2011; accepted 7 June 2011; online 18 June 2011)

The title compound, C₂₁H₂₁N₃O, was obtained by cyclocondensation of 3-amino-5-methyl-[1,1′-biphenyl]-2,4-dicarbonitrile with cyclohexanone. The six-membered 1,3-diaza ring assumes an envelope conformation [with the flap atom displaced by 0.511 (7) Å from the plane through the other ring atoms] and the cyclohexane ring displays a chair conformation. The dihedral angle between the aromatic rings is 42.61 (7)°.In the crystal, the molecules form hydrogen-bonded bands along [011].

Related literature

For the medicinal and biological properities of dihydroquinazolin-4(3H)-one derivatives, see: Deng et al. (2000 ); Chenard et al. (2000 ); Bertrand et al. (2001 ); Welch et al. (2001 ). For a related structure, see Zhang et al. (2008 )

Experimental

Crystal data

C₂₁H₂₁N₃O
M_r = 331.41
Triclinic, $[P \overline 1]$
a = 7.1824 (15) Å
b = 11.233 (3) Å
c = 11.430 (3) Å
α = 101.858 (8)°
β = 93.794 (9)°
γ = 104.606 (9)°
V = 866.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.35 × 0.27 × 0.27 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
9387 measured reflections
4521 independent reflections
3511 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.117
S = 1.00
4521 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯Olⁱ	0.920 (17)	1.998 (14)	2.9010 (17)	171.68 (14)
N1—H1N⋯N3ⁱⁱ	0.875 (18)	2.281 (14)	3.1188 (19)	160.24 (15)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z+1.

Data collection: CrystalClear (Rigaku, 2004 ); 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/S160053681102188X/ld2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102188X/ld2014Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102188X/ld2014Isup3.cml

checkCIF report

Comment top

The molecular structure of (I) is represented on Fig. 1. The 1,3-diaza ring exists in an envelope conformation with its C6 atom displaced by 0.511 (7)Å from the rest of the atoms of the ring (planar within 0.025 (1) Å). The geometry of the fused rings compares well with the related spiro[cyclopentane-1,2'(1'H)-quinazolin]-4'(3')-one] (Zhang et al., 2008). The crystal packing is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds forming alternating 8- and 12-membered centrosymmetric rings along [0 1 1] direction.

Related literature top

For the medicinal and biological properities of dihydroquinazolin-4(3H)-one derivatives, see: Deng et al. (2000); Chenard et al. (2000); Bertrand et al. (2001); Welch et al. (2001). For a related structure, see Zhang et al. (2008)

Experimental top

3-Amino-5-methyl-biphenyl-2,4-dicarbonitrile (0.1 mmol) was added to a mixture of cyclohexanone (3 ml) and sodium hydroxide (0.03 mmol). The reagents were heated at 373 K for 1.5 h. The reaction mixture was cooled to room temperature with water (15 ml) and then filtered to give the title compound. The product was recrystallizated from a mixed solvent (ethanol:petroleum ether 1:3) to give pale-yellow crystals.

M.p. 572–573 K. Spectra data: IR (KBr): 3329, 3067, 2934, 2221,1660, 1560, 1403, 697 cm^-1; ¹H-NMR(DMSO, p.p.m.):1.34–1.85 (10H, m, C₅H₁₀), 2.64 (3H, d, J = 1.4 Hz, CH₃), 6.42(1H, s, NH), 6.71 (1H, s, ArH), 7.49–7.53 (5H, m, ArH), 8.26 (1H, s, NH); ESI-MS m/z: [M+H]⁺ 332.1; C₂₁H₂₁N₃O:calcd. C 76.11, H 6.39, N 12.68; found C 76.12, H 6.55, N 12.06.

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); 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 x axis

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

Crystal data top

C₂₁H₂₁N₃O	Z = 2
M_r = 331.41	F(000) = 352
Triclinic, P1	D_x = 1.270 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1824 (15) Å	Cell parameters from 3260 reflections
b = 11.233 (3) Å	θ = 3.0–29.1°
c = 11.430 (3) Å	µ = 0.08 mm⁻¹
α = 101.858 (8)°	T = 153 K
β = 93.794 (9)°	Block, colorless
γ = 104.606 (9)°	0.35 × 0.27 × 0.27 mm
V = 866.6 (4) Å³

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	3511 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.024
Graphite monochromator	θ_max = 29.1°, θ_min = 3.0°
Detector resolution: 28.5714 pixels mm^-1	h = −9→7
phi and ω scans	k = −15→15
9387 measured reflections	l = −15→15
4521 independent 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)] = 0.048	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) + (0.0516P)² + 0.259P] where P = (F_o² + 2F_c²)/3
4521 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O	γ = 104.606 (9)°
M_r = 331.41	V = 866.6 (4) Å³
Triclinic, P1	Z = 2
a = 7.1824 (15) Å	Mo Kα radiation
b = 11.233 (3) Å	µ = 0.08 mm⁻¹
c = 11.430 (3) Å	T = 153 K
α = 101.858 (8)°	0.35 × 0.27 × 0.27 mm
β = 93.794 (9)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	3511 reflections with I > 2σ(I)
9387 measured reflections	R_int = 0.024
4521 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.35 e Å⁻³
4521 reflections	Δρ_min = −0.20 e Å⁻³
235 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 > 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
O1	0.79935 (15)	0.44593 (8)	0.06825 (9)	0.0303 (2)
N1	0.97094 (15)	0.77778 (10)	0.30982 (9)	0.0212 (2)
N2	1.00920 (15)	0.63845 (9)	0.13608 (9)	0.0201 (2)
N3	0.84792 (18)	0.93552 (12)	0.57411 (11)	0.0336 (3)
C1	1.26985 (18)	0.83252 (12)	0.22053 (11)	0.0212 (3)
H1A	1.3292	0.7806	0.2637	0.025*
H1B	1.2955	0.9177	0.2742	0.025*
C2	1.36630 (19)	0.84416 (12)	0.10637 (12)	0.0250 (3)
H2A	1.5044	0.8920	0.1293	0.030*
H2B	1.3612	0.7587	0.0593	0.030*
C3	1.2676 (2)	0.91080 (13)	0.02799 (13)	0.0290 (3)
H3A	1.3260	0.9095	−0.0482	0.035*
H3B	1.2883	1.0002	0.0704	0.035*
C4	1.0504 (2)	0.84591 (13)	−0.00007 (12)	0.0255 (3)
H4A	1.0296	0.7585	−0.0479	0.031*
H4B	0.9881	0.8920	−0.0488	0.031*
C5	0.95716 (18)	0.84267 (11)	0.11605 (11)	0.0214 (3)
H5A	0.8168	0.7998	0.0958	0.026*
H5B	0.9719	0.9302	0.1617	0.026*
C6	1.05070 (17)	0.77279 (11)	0.19470 (10)	0.0179 (2)
C7	0.78933 (17)	0.70442 (11)	0.31283 (10)	0.0185 (2)
C8	0.68158 (18)	0.73621 (11)	0.40828 (11)	0.0193 (2)
C9	0.49368 (18)	0.66095 (12)	0.41115 (11)	0.0203 (2)
C10	0.41853 (19)	0.55284 (12)	0.31972 (12)	0.0242 (3)
H10	0.2911	0.5021	0.3205	0.029*
C11	0.52333 (19)	0.51594 (12)	0.22663 (12)	0.0234 (3)
C12	0.71034 (18)	0.59166 (11)	0.22332 (10)	0.0190 (2)
C13	0.83918 (18)	0.55304 (11)	0.13493 (11)	0.0203 (2)
C14	0.77055 (18)	0.84636 (12)	0.50192 (11)	0.0224 (3)
C15	0.4289 (2)	0.39423 (14)	0.13529 (14)	0.0364 (4)
H15A	0.4901	0.3288	0.1491	0.044*
H15B	0.4446	0.4074	0.0540	0.044*
H15C	0.2905	0.3674	0.1434	0.044*
C16	0.37353 (18)	0.69620 (13)	0.50673 (11)	0.0228 (3)
C17	0.3629 (2)	0.82022 (14)	0.54351 (12)	0.0281 (3)
H17	0.4364	0.8841	0.5090	0.034*
C18	0.2455 (2)	0.85120 (17)	0.63036 (13)	0.0377 (4)
H18	0.2394	0.9361	0.6553	0.045*
C19	0.1375 (2)	0.75827 (19)	0.68029 (14)	0.0431 (4)
H19	0.0572	0.7793	0.7396	0.052*
C20	0.1462 (2)	0.63526 (18)	0.64427 (14)	0.0413 (4)
H20	0.0718	0.5717	0.6789	0.050*
C21	0.2633 (2)	0.60356 (15)	0.55756 (13)	0.0314 (3)
H21	0.2681	0.5184	0.5329	0.038*
H2N	1.081 (2)	0.6152 (15)	0.0762 (15)	0.034 (4)*
H1N	1.012 (3)	0.8526 (17)	0.3587 (16)	0.039 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0370 (6)	0.0169 (4)	0.0291 (5)	−0.0006 (4)	0.0161 (4)	−0.0058 (4)
N1	0.0228 (5)	0.0177 (5)	0.0172 (5)	0.0004 (4)	0.0073 (4)	−0.0041 (4)
N2	0.0229 (5)	0.0151 (5)	0.0203 (5)	0.0039 (4)	0.0092 (4)	−0.0010 (4)
N3	0.0293 (6)	0.0297 (6)	0.0331 (6)	0.0038 (5)	0.0098 (5)	−0.0087 (5)
C1	0.0185 (6)	0.0199 (6)	0.0211 (6)	0.0024 (5)	0.0036 (5)	−0.0010 (5)
C2	0.0197 (6)	0.0228 (6)	0.0266 (6)	0.0001 (5)	0.0080 (5)	−0.0024 (5)
C3	0.0287 (7)	0.0260 (7)	0.0285 (7)	−0.0013 (5)	0.0099 (5)	0.0064 (5)
C4	0.0276 (7)	0.0241 (6)	0.0227 (6)	0.0030 (5)	0.0041 (5)	0.0057 (5)
C5	0.0204 (6)	0.0178 (6)	0.0239 (6)	0.0038 (5)	0.0047 (5)	0.0014 (5)
C6	0.0193 (6)	0.0145 (5)	0.0170 (5)	0.0024 (4)	0.0060 (4)	−0.0012 (4)
C7	0.0210 (6)	0.0158 (5)	0.0173 (5)	0.0041 (4)	0.0050 (4)	0.0012 (4)
C8	0.0218 (6)	0.0174 (5)	0.0176 (5)	0.0055 (5)	0.0060 (4)	0.0000 (4)
C9	0.0210 (6)	0.0206 (6)	0.0204 (6)	0.0068 (5)	0.0066 (5)	0.0046 (5)
C10	0.0187 (6)	0.0232 (6)	0.0270 (6)	0.0015 (5)	0.0062 (5)	0.0015 (5)
C11	0.0230 (6)	0.0201 (6)	0.0230 (6)	0.0029 (5)	0.0052 (5)	−0.0009 (5)
C12	0.0218 (6)	0.0158 (5)	0.0172 (5)	0.0034 (5)	0.0050 (4)	0.0000 (4)
C13	0.0250 (6)	0.0167 (5)	0.0169 (5)	0.0036 (5)	0.0059 (5)	−0.0001 (4)
C14	0.0220 (6)	0.0233 (6)	0.0212 (6)	0.0067 (5)	0.0091 (5)	0.0009 (5)
C15	0.0278 (7)	0.0291 (7)	0.0365 (8)	−0.0064 (6)	0.0093 (6)	−0.0113 (6)
C16	0.0190 (6)	0.0307 (7)	0.0190 (6)	0.0080 (5)	0.0051 (5)	0.0039 (5)
C17	0.0264 (7)	0.0339 (7)	0.0236 (6)	0.0112 (6)	0.0058 (5)	0.0013 (5)
C18	0.0364 (8)	0.0506 (9)	0.0276 (7)	0.0229 (7)	0.0071 (6)	−0.0024 (7)
C19	0.0370 (9)	0.0760 (13)	0.0255 (7)	0.0292 (9)	0.0149 (6)	0.0114 (8)
C20	0.0318 (8)	0.0683 (12)	0.0357 (8)	0.0184 (8)	0.0173 (7)	0.0278 (8)
C21	0.0271 (7)	0.0408 (8)	0.0325 (7)	0.0123 (6)	0.0112 (6)	0.0158 (6)

Geometric parameters (Å, º) top

O1—C13	1.2374 (14)	C7—C8	1.4169 (15)
N1—C7	1.3628 (16)	C8—C9	1.4068 (17)
N1—C6	1.4658 (15)	C8—C14	1.4323 (17)
N1—H1N	0.875 (18)	C9—C10	1.3898 (17)
N2—C13	1.3468 (16)	C9—C16	1.4881 (16)
N2—C6	1.4650 (15)	C10—C11	1.3974 (17)
N2—H2N	0.920 (17)	C10—H10	0.9500
N3—C14	1.1453 (17)	C11—C12	1.4045 (17)
C1—C6	1.5295 (17)	C11—C15	1.5071 (18)
C1—C2	1.5310 (17)	C12—C13	1.4870 (16)
C1—H1A	0.9900	C15—H15A	0.9800
C1—H1B	0.9900	C15—H15B	0.9800
C2—C3	1.525 (2)	C15—H15C	0.9800
C2—H2A	0.9900	C16—C17	1.3931 (19)
C2—H2B	0.9900	C16—C21	1.3933 (19)
C3—C4	1.5268 (19)	C17—C18	1.3909 (18)
C3—H3A	0.9900	C17—H17	0.9500
C3—H3B	0.9900	C18—C19	1.383 (3)
C4—C5	1.5288 (17)	C18—H18	0.9500
C4—H4A	0.9900	C19—C20	1.377 (3)
C4—H4B	0.9900	C19—H19	0.9500
C5—C6	1.5335 (18)	C20—C21	1.3901 (19)
C5—H5A	0.9900	C20—H20	0.9500
C5—H5B	0.9900	C21—H21	0.9500
C7—C12	1.4147 (16)

C7—N1—C6	119.48 (10)	C12—C7—C8	119.21 (11)
C7—N1—H1N	119.5 (11)	C9—C8—C7	120.81 (11)
C6—N1—H1N	112.5 (11)	C9—C8—C14	121.21 (10)
C13—N2—C6	123.65 (10)	C7—C8—C14	117.97 (11)
C13—N2—H2N	114.8 (10)	C10—C9—C8	118.30 (11)
C6—N2—H2N	118.2 (10)	C10—C9—C16	119.88 (11)
C6—C1—C2	113.08 (10)	C8—C9—C16	121.80 (11)
C6—C1—H1A	109.0	C9—C10—C11	122.48 (12)
C2—C1—H1A	109.0	C9—C10—H10	118.8
C6—C1—H1B	109.0	C11—C10—H10	118.8
C2—C1—H1B	109.0	C10—C11—C12	119.18 (11)
H1A—C1—H1B	107.8	C10—C11—C15	117.49 (12)
C3—C2—C1	111.97 (11)	C12—C11—C15	123.33 (11)
C3—C2—H2A	109.2	C11—C12—C7	119.93 (10)
C1—C2—H2A	109.2	C11—C12—C13	122.62 (10)
C3—C2—H2B	109.2	C7—C12—C13	117.22 (11)
C1—C2—H2B	109.2	O1—C13—N2	121.02 (11)
H2A—C2—H2B	107.9	O1—C13—C12	122.42 (11)
C2—C3—C4	110.60 (11)	N2—C13—C12	116.43 (10)
C2—C3—H3A	109.5	N3—C14—C8	177.19 (13)
C4—C3—H3A	109.5	C11—C15—H15A	109.5
C2—C3—H3B	109.5	C11—C15—H15B	109.5
C4—C3—H3B	109.5	H15A—C15—H15B	109.5
H3A—C3—H3B	108.1	C11—C15—H15C	109.5
C3—C4—C5	110.76 (11)	H15A—C15—H15C	109.5
C3—C4—H4A	109.5	H15B—C15—H15C	109.5
C5—C4—H4A	109.5	C17—C16—C21	118.90 (12)
C3—C4—H4B	109.5	C17—C16—C9	121.09 (12)
C5—C4—H4B	109.5	C21—C16—C9	119.96 (12)
H4A—C4—H4B	108.1	C18—C17—C16	120.52 (14)
C4—C5—C6	111.17 (10)	C18—C17—H17	119.7
C4—C5—H5A	109.4	C16—C17—H17	119.7
C6—C5—H5A	109.4	C19—C18—C17	119.88 (15)
C4—C5—H5B	109.4	C19—C18—H18	120.1
C6—C5—H5B	109.4	C17—C18—H18	120.1
H5A—C5—H5B	108.0	C20—C19—C18	120.13 (13)
N2—C6—N1	106.03 (9)	C20—C19—H19	119.9
N2—C6—C1	110.11 (9)	C18—C19—H19	119.9
N1—C6—C1	108.50 (10)	C19—C20—C21	120.33 (15)
N2—C6—C5	110.77 (10)	C19—C20—H20	119.8
N1—C6—C5	111.09 (10)	C21—C20—H20	119.8
C1—C6—C5	110.24 (10)	C20—C21—C16	120.24 (15)
N1—C7—C12	119.96 (10)	C20—C21—H21	119.9
N1—C7—C8	120.76 (10)	C16—C21—H21	119.9

C6—C1—C2—C3	52.46 (14)	C9—C10—C11—C15	177.78 (13)
C1—C2—C3—C4	−53.99 (14)	C10—C11—C12—C7	−0.69 (19)
C2—C3—C4—C5	57.35 (14)	C15—C11—C12—C7	−179.68 (13)
C3—C4—C5—C6	−58.74 (14)	C10—C11—C12—C13	173.71 (12)
C13—N2—C6—N1	41.95 (15)	C15—C11—C12—C13	−5.3 (2)
C13—N2—C6—C1	159.13 (11)	N1—C7—C12—C11	179.85 (12)
C13—N2—C6—C5	−78.67 (14)	C8—C7—C12—C11	3.05 (18)
C7—N1—C6—N2	−45.90 (14)	N1—C7—C12—C13	5.16 (17)
C7—N1—C6—C1	−164.16 (10)	C8—C7—C12—C13	−171.65 (11)
C7—N1—C6—C5	74.51 (14)	C6—N2—C13—O1	168.01 (12)
C2—C1—C6—N2	69.94 (13)	C6—N2—C13—C12	−16.04 (17)
C2—C1—C6—N1	−174.42 (10)	C11—C12—C13—O1	−8.7 (2)
C2—C1—C6—C5	−52.57 (13)	C7—C12—C13—O1	165.83 (12)
C4—C5—C6—N2	−66.58 (13)	C11—C12—C13—N2	175.40 (12)
C4—C5—C6—N1	175.86 (10)	C7—C12—C13—N2	−10.05 (17)
C4—C5—C6—C1	55.55 (13)	C9—C8—C14—N3	−174 (3)
C6—N1—C7—C12	25.46 (17)	C7—C8—C14—N3	6 (3)
C6—N1—C7—C8	−157.79 (11)	C10—C9—C16—C17	−134.73 (14)
N1—C7—C8—C9	179.65 (11)	C8—C9—C16—C17	43.49 (19)
C12—C7—C8—C9	−3.57 (18)	C10—C9—C16—C21	42.70 (18)
N1—C7—C8—C14	−0.92 (18)	C8—C9—C16—C21	−139.07 (14)
C12—C7—C8—C14	175.86 (11)	C21—C16—C17—C18	0.6 (2)
C7—C8—C9—C10	1.68 (18)	C9—C16—C17—C18	178.05 (13)
C14—C8—C9—C10	−177.73 (12)	C16—C17—C18—C19	−0.3 (2)
C7—C8—C9—C16	−176.57 (12)	C17—C18—C19—C20	0.1 (2)
C14—C8—C9—C16	4.01 (19)	C18—C19—C20—C21	0.0 (3)
C8—C9—C10—C11	0.8 (2)	C19—C20—C21—C16	0.3 (2)
C16—C9—C10—C11	179.05 (12)	C17—C16—C21—C20	−0.6 (2)
C9—C10—C11—C12	−1.3 (2)	C9—C16—C21—C20	−178.06 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Olⁱ	0.920 (17)	1.998 (14)	2.9010 (17)	171.68 (14)
N1—H1N···N3ⁱⁱ	0.875 (18)	2.281 (14)	3.1188 (19)	160.24 (15)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O
M_r	331.41
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	7.1824 (15), 11.233 (3), 11.430 (3)
α, β, γ (°)	101.858 (8), 93.794 (9), 104.606 (9)
V (Å³)	866.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.27 × 0.27

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9387, 4521, 3511
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 1.00
No. of reflections	4521
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.20

Computer programs: CrystalClear (Rigaku, 2004), 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
N2—H2N···Olⁱ	0.920 (17)	1.998 (14)	2.9010 (17)	171.68 (14)
N1—H1N···N3ⁱⁱ	0.875 (18)	2.281 (14)	3.1188 (19)	160.24 (15)

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

Acknowledgements

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

References

Bertrand, L. C., Welch, W. M., Blake, J. F., Butler, T. W., Reinhold, A., Ewing, F. E., Menniti, F. S. & Pagnozzi, M. J. (2001). J. Med. Chem. 44, 1710–1717. Web of Science PubMed Google Scholar
Chenard, B. L., Menniti, F. S., Pagnozzi, M. J., Shenk, K. D., Ewing, F. E. & Welch, W. M. (2000). Bioorg. Med. Chem. Lett. 10, 1203–1205. Web of Science CrossRef PubMed CAS Google Scholar
Deng, Y. H., Yang, R. S. & Yang, Y. (2000). Chin. Pharm. Sci. 9, 116–118. CAS Google Scholar
Rigaku (2004). 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
Welch, W. M., Ewing, F. E., Huang, J., Menniti, F. S., Pagnozzi, M. J., Kelly, K., Seymour, P. A., Guanowsky, V., Guhan, S., Guinn, M. R., Critchett, D., Lazzaro, J., Ganong, A. H., Devries, K. M., Staigers, T. L. & Chenard, B. L. (2001). Bioorg. Med. Chem. Lett. 11, 177–181. 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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Volume 67| Part 7| July 2011| Page o1672

doi:10.1107/S160053681102188X

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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