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

The title compound, C(21)H(21)N(3)O, was obtained by cyclo-condensation of 3-amino-5-methyl-[1,1'-biphen-yl]-2,4-di-car-bo-nitrile with cyclo-hexa-none. 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 cyclo-hexane ring displays a chair conformation. The dihedral angle between the aromatic rings is 42.61 (7)°.In the crystal, the mol-ecules 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 = 331.41

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.117

S = 1.00

4521 reflections

235 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102188X/ld2014sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681102188X/ld2014Isup3.cml

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

C21H21N3O	Z = 2
Mr = 331.41	F(000) = 352
Triclinic, P1	Dx = 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

Rigaku AFC10/Saturn724+ diffractometer	3511 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.024
graphite	θmax = 29.1°, θmin = 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 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(Fo2) + (0.0516P)2 + 0.259P] where P = (Fo2 + 2Fc2)/3
4521 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .