2-(5-Chloro­pyridin-2-yl)-2,3-di­hydro-1H-iso­indole-1,3-dione

Holband, J.; Jurkin, M.; Wójcik, G.; Holband, T.

doi:10.1107/S1600536801003026

2-(5-Chloropyridin-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione

J. Holband, M. Jurkin, G. Wójcik and T. Holband

The title compound, C₁₃H₇ClN₂O₂, crystallizes in the centrosymmetric group P $\overline 1$ with one molecule in the asymmetric unit. The torsion angle between the phthalimidyl and chloropyridine moieties is about 45°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003026/cv6002sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003026/cv6002Isup2.hkl Contains datablock I

CCDC reference: 159860

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.119
Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.10
         From the CIF: _reflns_number_total               2342
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2476
         Completeness (_total/calc)             94.59%
          Alert C: < 95% complete

WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.124
          Weighting scheme identified as calc


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

The title compound, (I), a potential substrate for the synthesis of biologically active compounds, forms centrosymmetric triclinic crystals with one molecule in the asymmetric unit. Two rigid groups, phthalimidyl and chloropyridine, are connected in the molecule by a single C—N bond with the interplanar angle equal to 43.87 (4)°.

Experimental top

The title compound was obtained by melting 2-amino-5-chloropyridine with phthalic anhydride. After reaction, the solid mixture was dissolved in hot tetrahydrofuran and crystals were grown by slow cooling (m.p. 424–425 K).

Computing details top

Data collection: Kuma KM4CCD Software (Kuma, 1999); cell refinement: Kuma KM4CCD Software; data reduction: Kuma KM4CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. View of the title molecule. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. View of the packing in the title molecule.

1-(5-chloropyridin-2-yl)-isoindole-1,3-dione top

Crystal data top

C₁₃H₇ClN₂O₂	Z = 2
M_r = 258.66	F(000) = 264
Triclinic, P1	D_x = 1.528 Mg m⁻³ D_m = 1.530 Mg m⁻³ D_m measured by flotation
a = 7.494 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.974 (2) Å	Cell parameters from 1144 reflections
c = 10.303 (2) Å	θ = 3.4–24.5°
α = 100.58 (3)°	µ = 0.33 mm⁻¹
β = 98.38 (3)°	T = 298 K
γ = 107.98 (3)°	Prism, colourless
V = 562.00 (19) Å³	0.38 × 0.38 × 0.15 mm

Data collection top

Kuma Diffraction KM4CCD diffractometer	2244 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 27.1°, θ_min = 4.4°
ω scans	h = −9→5
3767 measured reflections	k = −10→10
2342 independent reflections	l = −13→13

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	Calculated w = 1/[σ²(F_o²) + (0.0757P)² + 0.1249P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.035
2342 reflections	Δρ_max = 0.24 e Å⁻³
164 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.104 (13)

Crystal data top

C₁₃H₇ClN₂O₂	γ = 107.98 (3)°
M_r = 258.66	V = 562.00 (19) Å³
Triclinic, P1	Z = 2
a = 7.494 (1) Å	Mo Kα radiation
b = 7.974 (2) Å	µ = 0.33 mm⁻¹
c = 10.303 (2) Å	T = 298 K
α = 100.58 (3)°	0.38 × 0.38 × 0.15 mm
β = 98.38 (3)°

Data collection top

Kuma Diffraction KM4CCD diffractometer	2244 reflections with I > 2σ(I)
3767 measured reflections	R_int = 0.016
2342 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
2342 reflections	Δρ_min = −0.27 e Å⁻³
164 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
Cl1	0.23507 (6)	0.24785 (6)	0.22275 (4)	0.05818 (19)
O1	0.26258 (19)	0.43129 (15)	−0.36847 (11)	0.0515 (3)
O2	0.26209 (16)	0.93644 (14)	−0.07226 (10)	0.0456 (3)
N1	0.12583 (17)	0.39366 (16)	−0.11877 (12)	0.0392 (3)
N2	0.24959 (17)	0.65566 (15)	−0.19346 (12)	0.0367 (3)
C1	0.25432 (18)	0.83670 (17)	−0.17756 (14)	0.0350 (3)
C2	0.24789 (18)	0.87237 (18)	−0.31399 (13)	0.0350 (3)
C3	0.2422 (2)	1.02542 (19)	−0.35652 (15)	0.0413 (3)
H3	0.2423	1.1280	−0.2965	0.050*
C4	0.2362 (2)	1.0200 (2)	−0.49305 (16)	0.0479 (4)
H4	0.2338	1.1214	−0.5247	0.058*
C5	0.2338 (3)	0.8662 (2)	−0.58266 (16)	0.0515 (4)
H5	0.2296	0.8661	−0.6733	0.062*
C6	0.2377 (3)	0.7120 (2)	−0.53904 (16)	0.0475 (4)
H6	0.2348	0.6081	−0.5990	0.057*
C7	0.2459 (2)	0.71894 (18)	−0.40381 (14)	0.0376 (3)
C8	0.2518 (2)	0.57856 (18)	−0.32855 (14)	0.0375 (3)
C9	0.24798 (19)	0.56417 (17)	−0.08728 (14)	0.0339 (3)
C10	0.36886 (19)	0.65214 (18)	0.03827 (14)	0.0372 (3)
H10	0.4504	0.7721	0.0555	0.045*
C11	0.3641 (2)	0.5556 (2)	0.13710 (14)	0.0393 (3)
H11	0.4417	0.6094	0.2232	0.047*
C12	0.2412 (2)	0.37717 (19)	0.10472 (14)	0.0376 (3)
C13	0.1248 (2)	0.30049 (19)	−0.02311 (15)	0.0404 (3)
H13	0.0431	0.1802	−0.0433	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0696 (3)	0.0594 (3)	0.0514 (3)	0.0185 (2)	0.0145 (2)	0.0331 (2)
O1	0.0815 (8)	0.0352 (6)	0.0449 (6)	0.0284 (5)	0.0175 (5)	0.0096 (4)
O2	0.0660 (7)	0.0355 (5)	0.0386 (5)	0.0214 (5)	0.0147 (5)	0.0073 (4)
N1	0.0449 (6)	0.0325 (6)	0.0373 (6)	0.0089 (5)	0.0072 (5)	0.0104 (5)
N2	0.0481 (6)	0.0291 (5)	0.0350 (6)	0.0148 (4)	0.0105 (5)	0.0094 (4)
C1	0.0388 (6)	0.0287 (6)	0.0389 (7)	0.0124 (5)	0.0088 (5)	0.0099 (5)
C2	0.0361 (6)	0.0312 (6)	0.0376 (7)	0.0111 (5)	0.0070 (5)	0.0100 (5)
C3	0.0482 (7)	0.0331 (7)	0.0444 (8)	0.0156 (6)	0.0078 (6)	0.0129 (6)
C4	0.0566 (8)	0.0434 (8)	0.0484 (8)	0.0187 (6)	0.0075 (6)	0.0229 (7)
C5	0.0649 (10)	0.0550 (9)	0.0374 (7)	0.0204 (7)	0.0100 (7)	0.0189 (7)
C6	0.0634 (9)	0.0438 (8)	0.0374 (7)	0.0199 (7)	0.0128 (6)	0.0111 (6)
C7	0.0442 (7)	0.0337 (6)	0.0370 (7)	0.0146 (5)	0.0097 (5)	0.0109 (5)
C8	0.0465 (7)	0.0310 (6)	0.0355 (7)	0.0139 (5)	0.0092 (5)	0.0083 (5)
C9	0.0390 (6)	0.0314 (6)	0.0356 (6)	0.0146 (5)	0.0113 (5)	0.0112 (5)
C10	0.0405 (6)	0.0317 (6)	0.0376 (7)	0.0104 (5)	0.0079 (5)	0.0082 (5)
C11	0.0418 (7)	0.0420 (7)	0.0340 (7)	0.0151 (5)	0.0071 (5)	0.0091 (5)
C12	0.0416 (7)	0.0398 (7)	0.0382 (7)	0.0168 (5)	0.0144 (5)	0.0166 (6)
C13	0.0457 (7)	0.0343 (7)	0.0408 (7)	0.0102 (5)	0.0117 (5)	0.0125 (5)

Geometric parameters (Å, º) top

Cl1—C12	1.7297 (15)	C4—H4	0.9300
O1—C8	1.2023 (17)	C5—C6	1.392 (2)
O2—C1	1.2038 (17)	C5—H5	0.9300
N1—C9	1.3323 (19)	C6—C7	1.376 (2)
N1—C13	1.3382 (18)	C6—H6	0.9300
N2—C1	1.4113 (16)	C7—C8	1.4817 (19)
N2—C8	1.4192 (18)	C9—C10	1.385 (2)
N2—C9	1.4215 (17)	C10—C11	1.383 (2)
C1—C2	1.4814 (19)	C10—H10	0.9300
C2—C3	1.3807 (19)	C11—C12	1.383 (2)
C2—C7	1.3865 (19)	C11—H11	0.9300
C3—C4	1.393 (2)	C12—C13	1.382 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.386 (2)

C9—N1—C13	117.28 (12)	C6—C7—C2	121.66 (14)
C1—N2—C8	111.11 (11)	C6—C7—C8	129.77 (13)
C1—N2—C9	124.44 (11)	C2—C7—C8	108.57 (12)
C8—N2—C9	124.44 (11)	O1—C8—N2	125.38 (13)
O2—C1—N2	125.01 (13)	O1—C8—C7	128.92 (13)
O2—C1—C2	129.18 (12)	N2—C8—C7	105.66 (11)
N2—C1—C2	105.81 (11)	N1—C9—C10	124.46 (13)
C3—C2—C7	121.33 (13)	N1—C9—N2	115.39 (12)
C3—C2—C1	129.94 (13)	C10—C9—N2	120.16 (12)
C7—C2—C1	108.73 (12)	C11—C10—C9	117.76 (12)
C2—C3—C4	117.28 (14)	C11—C10—H10	121.1
C2—C3—H3	121.4	C9—C10—H10	121.1
C4—C3—H3	121.4	C12—C11—C10	118.34 (13)
C5—C4—C3	121.25 (14)	C12—C11—H11	120.8
C5—C4—H4	119.4	C10—C11—H11	120.8
C3—C4—H4	119.4	C11—C12—C13	120.00 (13)
C4—C5—C6	121.03 (15)	C11—C12—Cl1	120.29 (12)
C4—C5—H5	119.5	C13—C12—Cl1	119.70 (11)
C6—C5—H5	119.5	N1—C13—C12	122.14 (13)
C7—C6—C5	117.45 (15)	N1—C13—H13	118.9
C7—C6—H6	121.3	C12—C13—H13	118.9
C5—C6—H6	121.3

C8—N2—C1—O2	−176.61 (13)	C1—N2—C8—C7	−3.50 (15)
C9—N2—C1—O2	1.8 (2)	C9—N2—C8—C7	178.06 (11)
C8—N2—C1—C2	3.37 (14)	C6—C7—C8—O1	5.1 (3)
C9—N2—C1—C2	−178.19 (11)	C2—C7—C8—O1	−175.56 (15)
O2—C1—C2—C3	−2.6 (2)	C6—C7—C8—N2	−177.11 (15)
N2—C1—C2—C3	177.42 (14)	C2—C7—C8—N2	2.22 (15)
O2—C1—C2—C7	178.10 (14)	C13—N1—C9—C10	−2.0 (2)
N2—C1—C2—C7	−1.88 (14)	C13—N1—C9—N2	177.65 (11)
C7—C2—C3—C4	−0.6 (2)	C1—N2—C9—N1	136.68 (14)
C1—C2—C3—C4	−179.81 (13)	C8—N2—C9—N1	−45.09 (18)
C2—C3—C4—C5	0.7 (2)	C1—N2—C9—C10	−43.67 (18)
C3—C4—C5—C6	−0.1 (3)	C8—N2—C9—C10	134.57 (14)
C4—C5—C6—C7	−0.7 (3)	N1—C9—C10—C11	0.9 (2)
C5—C6—C7—C2	0.8 (2)	N2—C9—C10—C11	−178.75 (11)
C5—C6—C7—C8	−179.93 (15)	C9—C10—C11—C12	0.7 (2)
C3—C2—C7—C6	−0.2 (2)	C10—C11—C12—C13	−1.0 (2)
C1—C2—C7—C6	179.17 (13)	C10—C11—C12—Cl1	177.92 (10)
C3—C2—C7—C8	−179.59 (12)	C9—N1—C13—C12	1.6 (2)
C1—C2—C7—C8	−0.22 (15)	C11—C12—C13—N1	−0.1 (2)
C1—N2—C8—O1	174.39 (14)	Cl1—C12—C13—N1	−179.07 (11)
C9—N2—C8—O1	−4.0 (2)

Experimental details

Crystal data
Chemical formula	C₁₃H₇ClN₂O₂
M_r	258.66
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.494 (1), 7.974 (2), 10.303 (2)
α, β, γ (°)	100.58 (3), 98.38 (3), 107.98 (3)
V (Å³)	562.00 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.38 × 0.38 × 0.15

Data collection
Diffractometer	Kuma Diffraction KM4CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3767, 2342, 2244
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.05
No. of reflections	2342
No. of parameters	164
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27

Computer programs: Kuma KM4CCD Software (Kuma, 1999), Kuma KM4CCD Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Cl1—C12	1.7297 (15)	N2—C8	1.4192 (18)
O1—C8	1.2023 (17)	N2—C9	1.4215 (17)
O2—C1	1.2038 (17)	C9—C10	1.385 (2)
N1—C9	1.3323 (19)	C10—C11	1.383 (2)
N1—C13	1.3382 (18)	C11—C12	1.383 (2)
N2—C1	1.4113 (16)	C12—C13	1.382 (2)

C9—N1—C13	117.28 (12)	N2—C8—C7	105.66 (11)
O2—C1—N2	125.01 (13)	N1—C9—N2	115.39 (12)
N2—C1—C2	105.81 (11)	C10—C9—N2	120.16 (12)
O1—C8—N2	125.38 (13)	C11—C12—C13	120.00 (13)

C9—N2—C1—O2	1.8 (2)	C8—N2—C9—N1	−45.09 (18)
C1—N2—C9—N1	136.68 (14)

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2-(5-Chloro­pyridin-2-yl)-2,3-di­hydro-1H-iso­indole-1,3-dione

Supporting information

Key indicators

checkCIF results

2-(5-Chloropyridin-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione