6'-Bromo-1'H-spiro-[cyclo-hexane-1,2'-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.

The title compound, C(12)H(14)BrN(3)O, is built up from two fused six-membered rings and one six-membered ring linked through a spiro C atom. The hydro-pyrimidine ring has an envelope conformation and the cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by N-H⋯O and N-H⋯N hydrogen bonds, forming a mol-ecular tape along the b axis.

Related literature

For medicinal and biological properties of 2,3-dihydro­pyrido[2,3-d]-pyrimidin-4(1H)-one derivatives, see: Parish et al. (1982 ▶); Narayana et al. (2009 ▶). For related structures, see: Shi et al. (2010 ▶); Ling et al. (2009 ▶).

Experimental

Crystal data

C12H14BrN3O

M = 296.17

Monoclinic,

a = 10.591 (3) Å

b = 12.359 (3) Å

c = 9.116 (3) Å

β = 97.951 (4)°

V = 1181.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.47 mm−1

T = 153 K

0.40 × 0.24 × 0.09 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.324, T max = 0.732

10128 measured reflections

3160 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.074

S = 1.00

3160 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.66 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); 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: CrystalStructure (Rigaku/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052299/is5001sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052299/is5001Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052299/is5001Isup3.cml

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

C12H14BrN3O	F(000) = 600
Mr = 296.17	Dx = 1.665 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3621 reflections
a = 10.591 (3) Å	θ = 2.6–29.1°
b = 12.359 (3) Å	µ = 3.47 mm−1
c = 9.116 (3) Å	T = 153 K
β = 97.951 (4)°	Platelet, colourless
V = 1181.7 (6) Å3	0.40 × 0.24 × 0.09 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	3160 independent reflections
Radiation source: Rotating Anode	2283 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.6°
φ and ω scans	h = −14→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −16→16
Tmin = 0.324, Tmax = 0.732	l = −12→12
10128 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0295P)2 + 0.126P] where P = (Fo2 + 2Fc2)/3
3160 reflections	(Δ/σ)max = 0.001
162 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

Experimental. Spectral data: IR (KBr): 3274, 3175, 2927, 1677, 1610, 1422 cm-1.

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
Br1	0.99820 (2)	0.65490 (2)	0.61599 (3)	0.03640 (10)
O1	0.58435 (14)	0.40734 (11)	0.39085 (16)	0.0171 (3)
N1	0.45035 (17)	0.52063 (14)	0.2500 (2)	0.0151 (4)
N2	0.49356 (17)	0.71034 (14)	0.2458 (2)	0.0188 (4)
N3	0.68151 (16)	0.78374 (13)	0.3597 (2)	0.0176 (4)
C1	0.2735 (2)	0.64979 (16)	0.2411 (2)	0.0150 (4)
H1A	0.2814	0.6418	0.3501	0.018*
H1B	0.2496	0.7257	0.2164	0.018*
C2	0.1676 (2)	0.57477 (17)	0.1687 (2)	0.0179 (5)
H2A	0.1865	0.4994	0.2015	0.021*
H2B	0.0855	0.5960	0.2005	0.021*
C3	0.1565 (2)	0.58081 (18)	−0.0002 (2)	0.0194 (5)
H3A	0.0902	0.5296	−0.0448	0.023*
H3B	0.1303	0.6547	−0.0336	0.023*
C4	0.2831 (2)	0.55308 (17)	−0.0524 (2)	0.0172 (5)
H4A	0.2751	0.5617	−0.1613	0.021*
H4B	0.3046	0.4765	−0.0285	0.021*
C5	0.3902 (2)	0.62565 (16)	0.0209 (2)	0.0160 (4)
H5A	0.3743	0.7006	−0.0152	0.019*
H5B	0.4717	0.6014	−0.0098	0.019*
C6	0.40340 (19)	0.62564 (15)	0.1905 (2)	0.0129 (4)
C7	0.55747 (19)	0.49967 (15)	0.3433 (2)	0.0127 (4)
C8	0.64262 (19)	0.59204 (16)	0.3832 (2)	0.0125 (4)
C9	0.6063 (2)	0.69577 (16)	0.3293 (2)	0.0139 (4)
C10	0.7594 (2)	0.57798 (17)	0.4683 (2)	0.0174 (5)
H10	0.7863	0.5086	0.5051	0.021*
C11	0.8365 (2)	0.66793 (17)	0.4987 (3)	0.0203 (5)
C12	0.7942 (2)	0.76778 (17)	0.4435 (3)	0.0203 (5)
H12	0.8482	0.8286	0.4665	0.024*
H1N	0.408 (2)	0.4668 (17)	0.220 (2)	0.015 (6)*
H2N	0.474 (2)	0.7700 (19)	0.208 (3)	0.026 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.02057 (13)	0.02781 (14)	0.05373 (19)	−0.00860 (11)	−0.01997 (11)	0.01191 (13)
O1	0.0199 (8)	0.0096 (7)	0.0194 (8)	0.0000 (6)	−0.0054 (6)	0.0021 (6)
N1	0.0143 (9)	0.0080 (8)	0.0209 (10)	−0.0027 (7)	−0.0049 (7)	−0.0002 (7)
N2	0.0163 (10)	0.0070 (9)	0.0298 (11)	−0.0006 (7)	−0.0085 (8)	0.0047 (8)
N3	0.0143 (10)	0.0111 (9)	0.0259 (11)	−0.0045 (7)	−0.0027 (8)	0.0016 (8)
C1	0.0165 (11)	0.0128 (10)	0.0153 (10)	0.0017 (9)	0.0011 (8)	−0.0012 (8)
C2	0.0133 (11)	0.0189 (11)	0.0216 (12)	−0.0025 (9)	0.0031 (9)	−0.0022 (9)
C3	0.0130 (11)	0.0208 (11)	0.0227 (12)	−0.0036 (9)	−0.0029 (9)	−0.0027 (10)
C4	0.0194 (11)	0.0184 (10)	0.0131 (10)	0.0000 (9)	−0.0003 (8)	−0.0017 (9)
C5	0.0167 (11)	0.0145 (10)	0.0175 (11)	0.0032 (8)	0.0050 (9)	0.0026 (9)
C6	0.0117 (10)	0.0070 (9)	0.0182 (11)	0.0004 (8)	−0.0042 (8)	0.0004 (8)
C7	0.0135 (10)	0.0112 (10)	0.0132 (10)	0.0009 (8)	0.0013 (8)	−0.0005 (8)
C8	0.0129 (10)	0.0113 (10)	0.0130 (10)	−0.0002 (8)	0.0006 (8)	−0.0005 (8)
C9	0.0137 (10)	0.0111 (9)	0.0165 (11)	−0.0006 (8)	0.0010 (8)	−0.0003 (8)
C10	0.0153 (11)	0.0151 (10)	0.0204 (11)	−0.0008 (9)	−0.0020 (9)	0.0041 (9)
C11	0.0120 (10)	0.0200 (11)	0.0262 (12)	−0.0040 (9)	−0.0064 (9)	0.0027 (10)
C12	0.0161 (11)	0.0148 (10)	0.0281 (13)	−0.0052 (9)	−0.0034 (9)	−0.0019 (10)

Br1—C11	1.896 (2)	C3—C4	1.523 (3)
O1—C7	1.240 (2)	C3—H3A	0.9900
N1—C7	1.346 (2)	C3—H3B	0.9900
N1—C6	1.467 (2)	C4—C5	1.525 (3)
N1—H1N	0.83 (2)	C4—H4A	0.9900
N2—C9	1.336 (3)	C4—H4B	0.9900
N2—C6	1.459 (3)	C5—C6	1.533 (3)
N2—H2N	0.83 (2)	C5—H5A	0.9900
N3—C12	1.339 (3)	C5—H5B	0.9900
N3—C9	1.354 (3)	C7—C8	1.469 (3)
C1—C2	1.533 (3)	C8—C10	1.377 (3)
C1—C6	1.539 (3)	C8—C9	1.407 (3)
C1—H1A	0.9900	C10—C11	1.384 (3)
C1—H1B	0.9900	C10—H10	0.9500
C2—C3	1.530 (3)	C11—C12	1.384 (3)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900
C7—N1—C6	128.11 (17)	C4—C5—C6	113.60 (18)
C7—N1—H1N	115.1 (15)	C4—C5—H5A	108.8
C6—N1—H1N	116.7 (15)	C6—C5—H5A	108.8
C9—N2—C6	126.21 (17)	C4—C5—H5B	108.8
C9—N2—H2N	120.3 (17)	C6—C5—H5B	108.8
C6—N2—H2N	112.6 (17)	H5A—C5—H5B	107.7
C12—N3—C9	116.82 (17)	N2—C6—N1	109.55 (16)
C2—C1—C6	112.62 (16)	N2—C6—C5	108.24 (17)
C2—C1—H1A	109.1	N1—C6—C5	110.62 (17)
C6—C1—H1A	109.1	N2—C6—C1	109.04 (16)
C2—C1—H1B	109.1	N1—C6—C1	109.38 (17)
C6—C1—H1B	109.1	C5—C6—C1	109.98 (16)
H1A—C1—H1B	107.8	O1—C7—N1	122.07 (18)
C3—C2—C1	110.73 (17)	O1—C7—C8	121.69 (18)
C3—C2—H2A	109.5	N1—C7—C8	116.22 (17)
C1—C2—H2A	109.5	C10—C8—C9	119.49 (18)
C3—C2—H2B	109.5	C10—C8—C7	120.94 (18)
C1—C2—H2B	109.5	C9—C8—C7	119.53 (18)
H2A—C2—H2B	108.1	N2—C9—N3	117.56 (18)
C4—C3—C2	110.80 (17)	N2—C9—C8	120.06 (18)
C4—C3—H3A	109.5	N3—C9—C8	122.37 (18)
C2—C3—H3A	109.5	C8—C10—C11	118.05 (19)
C4—C3—H3B	109.5	C8—C10—H10	121.0
C2—C3—H3B	109.5	C11—C10—H10	121.0
H3A—C3—H3B	108.1	C12—C11—C10	119.4 (2)
C3—C4—C5	111.35 (17)	C12—C11—Br1	120.17 (16)
C3—C4—H4A	109.4	C10—C11—Br1	120.42 (16)
C5—C4—H4A	109.4	N3—C12—C11	123.84 (19)
C3—C4—H4B	109.4	N3—C12—H12	118.1
C5—C4—H4B	109.4	C11—C12—H12	118.1
H4A—C4—H4B	108.0
C6—C1—C2—C3	−56.1 (2)	N1—C7—C8—C10	−174.77 (19)
C1—C2—C3—C4	56.8 (2)	O1—C7—C8—C9	−178.41 (19)
C2—C3—C4—C5	−55.7 (2)	N1—C7—C8—C9	3.0 (3)
C3—C4—C5—C6	54.2 (2)	C6—N2—C9—N3	174.7 (2)
C9—N2—C6—N1	4.4 (3)	C6—N2—C9—C8	−5.9 (3)
C9—N2—C6—C5	−116.3 (2)	C12—N3—C9—N2	180.0 (2)
C9—N2—C6—C1	124.1 (2)	C12—N3—C9—C8	0.6 (3)
C7—N1—C6—N2	1.1 (3)	C10—C8—C9—N2	179.6 (2)
C7—N1—C6—C5	120.3 (2)	C7—C8—C9—N2	1.8 (3)
C7—N1—C6—C1	−118.4 (2)	C10—C8—C9—N3	−1.0 (3)
C4—C5—C6—N2	−170.86 (16)	C7—C8—C9—N3	−178.8 (2)
C4—C5—C6—N1	69.1 (2)	C9—C8—C10—C11	0.6 (3)
C4—C5—C6—C1	−51.8 (2)	C7—C8—C10—C11	178.3 (2)
C2—C1—C6—N2	171.29 (17)	C8—C10—C11—C12	0.2 (3)
C2—C1—C6—N1	−68.9 (2)	C8—C10—C11—Br1	179.67 (16)
C2—C1—C6—C5	52.7 (2)	C9—N3—C12—C11	0.3 (3)
C6—N1—C7—O1	176.9 (2)	C10—C11—C12—N3	−0.6 (4)
C6—N1—C7—C8	−4.5 (3)	Br1—C11—C12—N3	179.88 (18)
O1—C7—C8—C10	3.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3i	0.83 (2)	2.52 (2)	3.337 (2)	169 (2)
N2—H2N···O1ii	0.83 (2)	1.98 (2)	2.807 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3i	0.83 (2)	2.52 (2)	3.337 (2)	169 (2)
N2—H2N⋯O1ii	0.83 (2)	1.98 (2)	2.807 (2)	175 (2)

Symmetry codes: (i) ; (ii) .