10′-Chloro-3′,4′-dihydro-2′H-spiro­[cyclo­propane-1,7′(6′H)-pyrimido[2,1-a]isoquinolin]-6′-one

Okuda, K.; Hirota, T.; Nishina, Y.; Ishida, H.

doi:10.1107/S1600536812044261

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3252

doi:10.1107/S1600536812044261

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10′-Chloro-3′,4′-dihydro-2′H-spiro[cyclopropane-1,7′(6′H)-pyrimido[2,1-a]isoquinolin]-6′-one

Kensuke Okuda,^a ^* Takashi Hirota,^b Yuta Nishina ^c and Hiroyuki Ishida ^d ^*

^aLaboratory of Medicinal and Pharmaceutical Chemistry, Gifu Pharmaceutical University, Gifu 501-1196, Japan, ^bLaboratory of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Okayama University, Okayama 700-8530, Japan, ^cResearch Core for Interdisciplinary Sciences, Okayama University, Okayama 700-8530, Japan, and ^dDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: okuda@gifu-pu.ac.jp, ishidah@cc.okayama-u.ac.jp

(Received 14 October 2012; accepted 25 October 2012; online 31 October 2012)

In the title compound, C₁₄H₁₃ClN₂O, the fused hydropyrimidine ring adopts an envelope conformation with one of the methylene C atoms at the flap. The three-membered ring is approximately perpendicular to the attached isoquinoline ring system, with a dihedral angle of 89.44 (11)°. In the crystal, molecules are linked by a weak C—H⋯π interaction, forming a helical chain along the c axis.

Related literature

For recent reports on the development of complex heterocyclic skeletons for potential pharmaceutics in one step using the Truce–Smiles rearrangement, see: Okuda et al. (2010 , 2011 ). For the synthesis of the title compound, see: Okuda et al. (2012 ).

Experimental

Crystal data

C₁₄H₁₃ClN₂O
M_r = 260.72
Orthorhombic, P c a 2₁
a = 8.8746 (5) Å
b = 13.3273 (7) Å
c = 9.8331 (6) Å
V = 1163.01 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 180 K
0.25 × 0.21 × 0.03 mm

Data collection

Rigaku R-AXIS RAPIDII diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.931, T_max = 0.991
17373 measured reflections
3359 independent reflections
3095 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.079
S = 1.05
3359 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), 1571 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/N1/C2–C4/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯Cg1ⁱ	0.99	2.72	3.6000 (15)	148
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044261/ff2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044261/ff2085Isup2.hkl

checkCIF report

Comment top

As an extension of our work to develop complex heterocyclic skeletons as leads for potential pharmaceutical agents (Okuda et al., 2011), we found that tricyclic 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines (Okuda et al., 2010), easily accessible by a one step base-induced Truce-Smiles rearrangement of 2-(3-cyanopropoxy)benzonitriles, showed bronchodilator activity (unpublished results). In the pursuit of more potent analogs, we have explored preparation of additional new ring-fused tetracyclic heterocycles. Herein we report that reaction of 5-amino-7-chloro-1,2-dihydrofuro[2,3-c]isoquinoline with 1,3-dibromopropane in the presence of calcium oxide afforded the title compound (Okuda et al., 2012) via rearrangement instead of the anticipated 10-chloro-2,3,6,7-tetrahydrofuro[2,3-c]imidazo[2,1-a]isoquinoline.

In the title compound, the fused hydropyrimidine N1/C1/N2/C12–C14 ring adopts an envelope conformation with atom C13 at the flap. The isoquinoline C1/N1/C2–C9 ring system is planar with an r.m.s. deviation of 0.044 (1) Å. The three-membered C3/C10/C11 ring is approximately perpendicular to the attached isoquinoline ring system with a dihedral angle of 89.44 (11)°. In the crystal, molecules are linked by a weak C—H···π interaction (Table 1), forming a helical chain along the c axis.

Related literature top

For recent reports on the development of complex heterocyclic skeletons for potential pharmaceutics in one step using the Truce–Smiles rearrangement, see: Okuda et al. (2010, 2011). For the synthesis of the title compound, see: Okuda et al. (2012).

Experimental top

The detailed experimental procedure for the synthesis of 10'-chloro-3',4'-dihydro-2'H-spiro[cyclopropane-1,7'(6'H)-pyrimido[2,1-a]isoquinolin]-6'-one (m.p. 424–425 K from n-hexane) from 5-amino-7-chloro-1,2-dihydrofuro[2,3-c]isoquinoline was described in our previous paper (Okuda et al., 2012). Single crystals suitable for X-ray diffraction were obtained from an acetonitrile/water solution. The title compound was dissolved in hot acetonitrile, then water was added dropwise until the solution became turbid. Slow evaporation at room temperature gave the colourless crystals

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-labeling. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, showing a chain structure formed by C—H···π interactions (dashed lines).

10'-Chloro-3',4'-dihydro-2'H-spiro[cyclopropane- 1,7'(6'H)-pyrimido[2,1-a]isoquinolin]-6'-one top

Crystal data top

C₁₄H₁₃ClN₂O	F(000) = 544.00
M_r = 260.72	D_x = 1.489 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2ac	Cell parameters from 15021 reflections
a = 8.8746 (5) Å	θ = 3.1–30.0°
b = 13.3273 (7) Å	µ = 0.32 mm⁻¹
c = 9.8331 (6) Å	T = 180 K
V = 1163.01 (11) Å³	Platelet, colourless
Z = 4	0.25 × 0.21 × 0.03 mm

Data collection top

Rigaku R-AXIS RAPIDII diffractometer	3095 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 30.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −12→12
T_min = 0.931, T_max = 0.991	k = −18→18
17373 measured reflections	l = −13→13
3359 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0483P)² + 0.1225P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3359 reflections	Δρ_max = 0.32 e Å⁻³
163 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1571 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Crystal data top

C₁₄H₁₃ClN₂O	V = 1163.01 (11) Å³
M_r = 260.72	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.8746 (5) Å	µ = 0.32 mm⁻¹
b = 13.3273 (7) Å	T = 180 K
c = 9.8331 (6) Å	0.25 × 0.21 × 0.03 mm

Data collection top

Rigaku R-AXIS RAPIDII diffractometer	3359 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3095 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.991	R_int = 0.027
17373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.079	Δρ_max = 0.32 e Å⁻³
S = 1.05	Δρ_min = −0.15 e Å⁻³
3359 reflections	Absolute structure: Flack (1983), 1571 Friedel pairs
163 parameters	Absolute structure parameter: 0.01 (5)
1 restraint

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
Cl1	0.55266 (4)	0.63700 (2)	0.30542 (5)	0.03531 (10)
O1	0.57503 (12)	0.04186 (7)	0.43848 (12)	0.0307 (2)
N1	0.45976 (11)	0.15982 (7)	0.31067 (13)	0.01989 (19)
N2	0.36794 (13)	0.28236 (8)	0.15502 (12)	0.0249 (2)
C1	0.44659 (13)	0.25802 (10)	0.25827 (13)	0.0189 (2)
C2	0.56200 (15)	0.13087 (10)	0.40789 (14)	0.0211 (2)
C3	0.65462 (14)	0.20982 (9)	0.47518 (13)	0.0205 (2)
C4	0.63116 (14)	0.31618 (9)	0.43507 (12)	0.0191 (2)
C5	0.70816 (15)	0.39510 (11)	0.49866 (14)	0.0259 (3)
H5	0.7774	0.3806	0.5697	0.031*
C6	0.68510 (16)	0.49385 (10)	0.45973 (15)	0.0260 (3)
H6	0.7372	0.5470	0.5038	0.031*
C7	0.58418 (16)	0.51363 (10)	0.35496 (15)	0.0242 (3)
C8	0.50749 (14)	0.43794 (9)	0.28990 (14)	0.0226 (2)
H8	0.4391	0.4531	0.2185	0.027*
C9	0.53128 (13)	0.33791 (9)	0.33006 (13)	0.0187 (2)
C10	0.81354 (17)	0.17547 (12)	0.51350 (16)	0.0301 (3)
H10A	0.8443	0.1069	0.4865	0.036*
H10B	0.8952	0.2260	0.5108	0.036*
C11	0.69779 (19)	0.18535 (11)	0.62195 (15)	0.0293 (3)
H11A	0.7079	0.2420	0.6864	0.035*
H11B	0.6570	0.1229	0.6621	0.035*
C12	0.27594 (16)	0.20671 (11)	0.08694 (15)	0.0297 (3)
H12A	0.3328	0.1794	0.0086	0.036*
H12B	0.1836	0.2390	0.0513	0.036*
C13	0.23159 (15)	0.12115 (11)	0.17992 (16)	0.0289 (3)
H13A	0.1610	0.1456	0.2505	0.035*
H13B	0.1802	0.0681	0.1268	0.035*
C14	0.37139 (16)	0.07873 (10)	0.24647 (16)	0.0267 (3)
H14A	0.3421	0.0288	0.3162	0.032*
H14B	0.4338	0.0443	0.1773	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.04450 (18)	0.01793 (13)	0.0435 (2)	−0.00198 (13)	0.00151 (18)	0.00384 (15)
O1	0.0391 (5)	0.0195 (5)	0.0334 (6)	−0.0010 (4)	−0.0080 (5)	0.0010 (4)
N1	0.0222 (4)	0.0189 (4)	0.0186 (5)	−0.0024 (3)	−0.0003 (4)	−0.0022 (5)
N2	0.0257 (5)	0.0269 (5)	0.0221 (5)	−0.0025 (4)	−0.0051 (4)	0.0002 (4)
C1	0.0193 (5)	0.0197 (5)	0.0177 (5)	0.0001 (4)	0.0020 (4)	−0.0015 (4)
C2	0.0244 (5)	0.0197 (6)	0.0190 (6)	−0.0007 (4)	0.0012 (4)	0.0000 (4)
C3	0.0227 (5)	0.0201 (5)	0.0187 (5)	−0.0006 (4)	−0.0026 (4)	−0.0005 (4)
C4	0.0205 (5)	0.0185 (5)	0.0184 (5)	−0.0011 (4)	0.0005 (4)	−0.0012 (4)
C5	0.0280 (6)	0.0252 (6)	0.0245 (6)	−0.0031 (5)	−0.0051 (5)	−0.0013 (5)
C6	0.0295 (6)	0.0215 (6)	0.0270 (7)	−0.0065 (5)	0.0022 (5)	−0.0046 (5)
C7	0.0279 (6)	0.0176 (5)	0.0272 (6)	−0.0009 (5)	0.0069 (5)	0.0009 (5)
C8	0.0239 (5)	0.0209 (5)	0.0231 (6)	0.0005 (4)	0.0005 (5)	0.0008 (5)
C9	0.0193 (5)	0.0194 (5)	0.0174 (6)	−0.0005 (4)	0.0020 (4)	−0.0013 (4)
C10	0.0273 (7)	0.0278 (7)	0.0351 (8)	0.0024 (6)	−0.0106 (6)	−0.0001 (6)
C11	0.0407 (8)	0.0257 (6)	0.0214 (6)	−0.0004 (6)	−0.0089 (6)	0.0032 (5)
C12	0.0302 (7)	0.0331 (7)	0.0259 (7)	−0.0057 (6)	−0.0092 (6)	−0.0028 (5)
C13	0.0256 (6)	0.0330 (7)	0.0281 (7)	−0.0072 (5)	−0.0040 (5)	−0.0051 (6)
C14	0.0321 (6)	0.0200 (6)	0.0282 (6)	−0.0051 (5)	−0.0052 (5)	−0.0039 (5)

Geometric parameters (Å, º) top

Cl1—C7	1.7376 (14)	C6—H6	0.9500
O1—C2	1.2292 (16)	C7—C8	1.3748 (19)
N1—C2	1.3733 (17)	C8—C9	1.4063 (17)
N1—C1	1.4113 (16)	C8—H8	0.9500
N1—C14	1.4769 (16)	C10—C11	1.486 (2)
N2—C1	1.2740 (17)	C10—H10A	0.9900
N2—C12	1.4599 (17)	C10—H10B	0.9900
C1—C9	1.4822 (17)	C11—H11A	0.9900
C2—C3	1.4902 (18)	C11—H11B	0.9900
C3—C4	1.4859 (17)	C12—C13	1.514 (2)
C3—C11	1.5284 (19)	C12—H12A	0.9900
C3—C10	1.5299 (19)	C12—H12B	0.9900
C4—C9	1.3913 (17)	C13—C14	1.512 (2)
C4—C5	1.4015 (18)	C13—H13A	0.9900
C5—C6	1.3859 (19)	C13—H13B	0.9900
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.390 (2)	C14—H14B	0.9900

C2—N1—C1	124.71 (10)	C4—C9—C1	121.81 (11)
C2—N1—C14	116.28 (10)	C8—C9—C1	118.10 (11)
C1—N1—C14	118.59 (11)	C11—C10—C3	60.87 (9)
C1—N2—C12	119.73 (12)	C11—C10—H10A	117.7
N2—C1—N1	124.92 (12)	C3—C10—H10A	117.7
N2—C1—C9	118.32 (12)	C11—C10—H10B	117.7
N1—C1—C9	116.76 (11)	C3—C10—H10B	117.7
O1—C2—N1	120.24 (12)	H10A—C10—H10B	114.8
O1—C2—C3	121.39 (12)	C10—C11—C3	60.97 (9)
N1—C2—C3	118.37 (11)	C10—C11—H11A	117.7
C4—C3—C2	118.58 (11)	C3—C11—H11A	117.7
C4—C3—C11	119.30 (11)	C10—C11—H11B	117.7
C2—C3—C11	114.01 (11)	C3—C11—H11B	117.7
C4—C3—C10	118.68 (11)	H11A—C11—H11B	114.8
C2—C3—C10	113.99 (11)	N2—C12—C13	112.88 (12)
C11—C3—C10	58.16 (9)	N2—C12—H12A	109.0
C9—C4—C5	119.05 (11)	C13—C12—H12A	109.0
C9—C4—C3	119.00 (11)	N2—C12—H12B	109.0
C5—C4—C3	121.94 (11)	C13—C12—H12B	109.0
C6—C5—C4	121.16 (12)	H12A—C12—H12B	107.8
C6—C5—H5	119.4	C14—C13—C12	109.24 (11)
C4—C5—H5	119.4	C14—C13—H13A	109.8
C5—C6—C7	118.68 (12)	C12—C13—H13A	109.8
C5—C6—H6	120.7	C14—C13—H13B	109.8
C7—C6—H6	120.7	C12—C13—H13B	109.8
C8—C7—C6	121.64 (12)	H13A—C13—H13B	108.3
C8—C7—Cl1	118.96 (11)	N1—C14—C13	110.31 (11)
C6—C7—Cl1	119.40 (10)	N1—C14—H14A	109.6
C7—C8—C9	119.38 (12)	C13—C14—H14A	109.6
C7—C8—H8	120.3	N1—C14—H14B	109.6
C9—C8—H8	120.3	C13—C14—H14B	109.6
C4—C9—C8	120.09 (11)	H14A—C14—H14B	108.1

C12—N2—C1—N1	3.66 (19)	C4—C5—C6—C7	−0.4 (2)
C12—N2—C1—C9	−176.29 (11)	C5—C6—C7—C8	0.0 (2)
C2—N1—C1—N2	169.27 (13)	C5—C6—C7—Cl1	179.55 (11)
C14—N1—C1—N2	−2.93 (19)	C6—C7—C8—C9	0.1 (2)
C2—N1—C1—C9	−10.78 (18)	Cl1—C7—C8—C9	−179.46 (10)
C14—N1—C1—C9	177.02 (11)	C5—C4—C9—C8	−0.63 (18)
C1—N1—C2—O1	−173.21 (13)	C3—C4—C9—C8	−179.79 (11)
C14—N1—C2—O1	−0.84 (19)	C5—C4—C9—C1	179.82 (11)
C1—N1—C2—C3	7.29 (19)	C3—C4—C9—C1	0.66 (17)
C14—N1—C2—C3	179.66 (12)	C7—C8—C9—C4	0.24 (18)
O1—C2—C3—C4	−178.91 (12)	C7—C8—C9—C1	179.81 (11)
N1—C2—C3—C4	0.58 (18)	N2—C1—C9—C4	−173.56 (12)
O1—C2—C3—C11	−30.41 (18)	N1—C1—C9—C4	6.49 (17)
N1—C2—C3—C11	149.08 (13)	N2—C1—C9—C8	6.88 (17)
O1—C2—C3—C10	33.87 (19)	N1—C1—C9—C8	−173.07 (11)
N1—C2—C3—C10	−146.63 (13)	C4—C3—C10—C11	108.47 (14)
C2—C3—C4—C9	−4.26 (17)	C2—C3—C10—C11	−104.35 (13)
C11—C3—C4—C9	−151.08 (12)	C4—C3—C11—C10	−107.42 (14)
C10—C3—C4—C9	141.41 (12)	C2—C3—C11—C10	104.32 (13)
C2—C3—C4—C5	176.60 (12)	C1—N2—C12—C13	25.27 (18)
C11—C3—C4—C5	29.78 (18)	N2—C12—C13—C14	−52.69 (16)
C10—C3—C4—C5	−37.73 (18)	C2—N1—C14—C13	160.89 (12)
C9—C4—C5—C6	0.73 (19)	C1—N1—C14—C13	−26.25 (17)
C3—C4—C5—C6	179.87 (13)	C12—C13—C14—N1	51.96 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1/N1/C2–C4/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cg1ⁱ	0.99	2.72	3.6000 (15)	148

Symmetry code: (i) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃ClN₂O
M_r	260.72
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	180
a, b, c (Å)	8.8746 (5), 13.3273 (7), 9.8331 (6)
V (Å³)	1163.01 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.25 × 0.21 × 0.03

Data collection
Diffractometer	Rigaku R-AXIS RAPIDII diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.931, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	17373, 3359, 3095
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 1.05
No. of reflections	3359
No. of parameters	163
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.15
Absolute structure	Flack (1983), 1571 Friedel pairs
Absolute structure parameter	0.01 (5)

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1/N1/C2–C4/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cg1ⁱ	0.99	2.72	3.6000 (15)	148

Symmetry code: (i) −x+1/2, y, z−1/2.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Okuda, K., Takechi, H., Hirota, T. & Sasaki, K. (2011). Heterocycles, 83, 1315–1328. Web of Science CrossRef CAS Google Scholar
Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2010). Chem. Pharm. Bull. 58, 363–368. CrossRef CAS PubMed Google Scholar
Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2012). Synth. Commun. 42, 865–871. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3252

doi:10.1107/S1600536812044261

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

10′-Chloro-3′,4′-di­hydro-2′H-spiro­[cyclo­propane-1,7′(6′H)-pyrimido[2,1-a]isoquinolin]-6′-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

10′-Chloro-3′,4′-dihydro-2′H-spiro[cyclopropane-1,7′(6′H)-pyrimido[2,1-a]isoquinolin]-6′-one