N-(8-Quinolyl­amino)­phthal­imide

Lynch, D.E.; McClenaghan, I.

doi:10.1107/S1600536800018109

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N-(8-Quinolylamino)phthalimide

D. E. Lynch and I. McClenaghan

The structure of the title compound, C₁₇H₁₁N₃O₂, (I), comprises twisted molecules that associate via a single N—H

O intermolecular interaction, forming a linear one-dimensional hydrogen-bonded chain. The dihedral angle between the two ring systems is 89.9 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018109/na6002sup1.cif Contains datablocks I, default
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018109/na6002Isup2.hkl Contains datablock I

CCDC reference: 155859

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.099
Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.52
         From the CIF: _reflns_number_total               1676
         Count of symmetry unique reflns         1683
         Completeness (_total/calc)             99.58%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

NO COMMENT

Experimental top

Crystals of (I) were obtained from Spa Contract Synthesis.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

'8-(Isoindol-1,3-dione-2-yl)aminoquinoline' top

Crystal data top

C₁₇H₁₁N₃O₂	D_x = 1.411 Mg m⁻³
M_r = 289.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 4257 reflections
a = 16.397 (3) Å	θ = 1.0–27.5°
b = 10.819 (2) Å	µ = 0.10 mm⁻¹
c = 7.6737 (15) Å	T = 150 K
V = 1361.4 (5) Å³	Needle, yellow
Z = 4	0.26 × 0.12 × 0.04 mm
F(000) = 600

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1676 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1350 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −21→19
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→13
T_min = 0.976, T_max = 0.996	l = −9→9
8737 measured 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.049P)²] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
1676 reflections	Δρ_max = 0.54 e Å⁻³
204 parameters	Δρ_min = −0.44 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (5)

Crystal data top

C₁₇H₁₁N₃O₂	V = 1361.4 (5) Å³
M_r = 289.29	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.397 (3) Å	µ = 0.10 mm⁻¹
b = 10.819 (2) Å	T = 150 K
c = 7.6737 (15) Å	0.26 × 0.12 × 0.04 mm

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1676 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1350 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.996	R_int = 0.070
8737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.099	H-atom parameters constrained
S = 1.18	Δρ_max = 0.54 e Å⁻³
1676 reflections	Δρ_min = −0.44 e Å⁻³
204 parameters

Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.4179 (0.0104) x - 5.9910 (0.0092) y + 1.1834 (0.0092) z = 1.7870 (0.0075)

* 0.0080 (0.0018) N1 * -0.0074 (0.0019) C2 * 0.0014 (0.0020) C3 * 0.0034 (0.0020) C4 * -0.0025 (0.0018) C10 * -0.0030 (0.0018) C9 - 0.0227 (0.0045) C5 - 0.0567 (0.0052) C6 - 0.0492 (0.0048) C7 - 0.0146 (0.0039) C8 - 0.0937 (0.0043) N81

Rms deviation of fitted atoms = 0.0050

1.1606 (0.0211) x + 3.9059 (0.0129) y + 7.1356 (0.0039) z = 3.1123 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 89.92 (0.10)

* -0.0043 (0.0016) C11 * 0.0074 (0.0016) N12 * -0.0073 (0.0015) C13 * 0.0046 (0.0016) C19 * -0.0004 (0.0016) C18 0.0294 (0.0044) C14 0.0416 (0.0055) C15 0.0294 (0.0054) C16 0.0105 (0.0045) C17 - 0.0292 (0.0040) O11 - 0.0286 (0.0039) O13 - 0.0509 (0.0041) N81

Rms deviation of fitted atoms = 0.0054

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	−0.09061 (14)	−0.3749 (2)	0.6464 (3)	0.0275 (5)
C2	−0.13724 (18)	−0.4657 (3)	0.7020 (3)	0.0326 (7)
H2	−0.1503	−0.4681	0.8226	0.041*
C3	−0.16898 (17)	−0.5594 (2)	0.5953 (4)	0.0343 (7)
H3	−0.2015	−0.6235	0.6433	0.043*
C4	−0.15233 (18)	−0.5566 (2)	0.4225 (4)	0.0316 (6)
H4	−0.1733	−0.6191	0.3480	0.040*
C5	−0.08492 (16)	−0.4502 (2)	0.1746 (3)	0.0306 (7)
H5	−0.1041	−0.5105	0.0946	0.038*
C6	−0.03895 (17)	−0.3530 (2)	0.1168 (4)	0.0332 (6)
H6	−0.0272	−0.3456	−0.0040	0.041*
C7	−0.00890 (16)	−0.2638 (2)	0.2340 (4)	0.0288 (6)
H7	0.0232	−0.1971	0.1917	0.036*
C8	−0.02552 (16)	−0.2723 (2)	0.4086 (3)	0.0241 (5)
C9	−0.07421 (15)	−0.3708 (2)	0.4719 (3)	0.0230 (6)
C10	−0.10386 (17)	−0.4607 (2)	0.3534 (3)	0.0272 (6)
N81	−0.00131 (13)	−0.18119 (19)	0.5284 (3)	0.0263 (5)
H81	−0.0055 (16)	−0.208 (3)	0.639 (4)	0.031 (8)*
C11	0.06871 (16)	0.0046 (2)	0.4219 (3)	0.0258 (6)
O11	0.00804 (11)	0.06545 (16)	0.3949 (3)	0.0319 (5)
N12	0.06876 (12)	−0.11626 (19)	0.4897 (3)	0.0255 (5)
C13	0.14796 (17)	−0.1653 (2)	0.5015 (3)	0.0286 (6)
O13	0.16305 (12)	−0.26878 (16)	0.5528 (3)	0.0393 (5)
C14	0.28647 (16)	−0.0627 (3)	0.4280 (4)	0.0305 (6)
H14	0.3189	−0.1315	0.4616	0.038*
C15	0.32202 (18)	0.0448 (3)	0.3651 (4)	0.0342 (7)
H15	0.3797	0.0498	0.3554	0.043*
C16	0.27438 (17)	0.1451 (3)	0.3162 (4)	0.0334 (7)
H16	0.3001	0.2176	0.2730	0.042*
C17	0.19009 (17)	0.1416 (3)	0.3292 (3)	0.0288 (6)
H17	0.1576	0.2104	0.2961	0.036*
C18	0.15523 (16)	0.0348 (2)	0.3918 (3)	0.0255 (6)
C19	0.20287 (16)	−0.0664 (2)	0.4402 (3)	0.0256 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0315 (12)	0.0243 (12)	0.0268 (13)	−0.0019 (10)	0.0009 (9)	−0.0006 (9)
C2	0.0391 (17)	0.0317 (16)	0.0272 (15)	−0.0065 (13)	0.0045 (12)	0.0028 (11)
C3	0.0374 (17)	0.0258 (16)	0.0395 (18)	−0.0096 (12)	−0.0003 (12)	0.0026 (12)
C4	0.0369 (16)	0.0224 (14)	0.0356 (16)	−0.0042 (12)	−0.0076 (12)	−0.0035 (12)
C5	0.0425 (18)	0.0252 (15)	0.0240 (13)	0.0003 (12)	−0.0055 (12)	−0.0041 (11)
C6	0.0431 (17)	0.0305 (15)	0.0259 (13)	0.0042 (14)	0.0008 (12)	0.0011 (11)
C7	0.0330 (15)	0.0240 (15)	0.0295 (14)	−0.0014 (12)	0.0018 (11)	0.0034 (11)
C8	0.0236 (13)	0.0193 (12)	0.0295 (14)	0.0037 (11)	−0.0002 (10)	−0.0009 (11)
C9	0.0244 (14)	0.0192 (13)	0.0254 (13)	0.0023 (11)	−0.0006 (10)	−0.0015 (10)
C10	0.0310 (15)	0.0209 (13)	0.0297 (14)	0.0012 (12)	−0.0028 (11)	−0.0018 (10)
N81	0.0299 (13)	0.0207 (12)	0.0281 (13)	−0.0085 (9)	0.0042 (9)	−0.0018 (10)
C11	0.0293 (15)	0.0207 (13)	0.0275 (13)	−0.0013 (12)	−0.0009 (11)	−0.0017 (10)
O11	0.0274 (11)	0.0239 (10)	0.0445 (12)	0.0012 (8)	−0.0021 (8)	0.0027 (9)
N12	0.0247 (12)	0.0187 (11)	0.0332 (12)	−0.0030 (10)	0.0006 (8)	0.0039 (9)
C13	0.0327 (16)	0.0257 (14)	0.0274 (14)	0.0025 (12)	−0.0010 (10)	0.0017 (11)
O13	0.0418 (12)	0.0236 (10)	0.0525 (13)	0.0015 (9)	−0.0037 (9)	0.0118 (10)
C14	0.0287 (15)	0.0269 (14)	0.0358 (15)	0.0033 (12)	−0.0030 (12)	0.0028 (11)
C15	0.0283 (15)	0.0360 (16)	0.0383 (16)	−0.0029 (13)	−0.0009 (11)	0.0010 (13)
C16	0.0362 (17)	0.0264 (14)	0.0377 (16)	−0.0078 (13)	0.0000 (12)	0.0044 (12)
C17	0.0320 (15)	0.0227 (14)	0.0317 (14)	−0.0014 (13)	−0.0058 (12)	0.0041 (11)
C18	0.0285 (14)	0.0202 (13)	0.0277 (13)	−0.0004 (11)	−0.0015 (10)	0.0006 (11)
C19	0.0296 (15)	0.0203 (13)	0.0268 (13)	−0.0007 (12)	−0.0022 (11)	0.0003 (10)

Geometric parameters (Å, º) top

N1—C2	1.317 (3)	N81—N12	1.379 (3)
N1—C9	1.367 (3)	N81—H81	0.90 (3)
C2—C3	1.403 (4)	C11—O11	1.211 (3)
C2—H2	0.9500	C11—N12	1.407 (3)
C3—C4	1.354 (4)	C11—C18	1.474 (4)
C3—H3	0.9500	N12—C13	1.406 (3)
C4—C10	1.411 (4)	C13—O13	1.213 (3)
C4—H4	0.9500	C13—C19	1.475 (4)
C5—C6	1.368 (4)	C14—C19	1.375 (4)
C5—C10	1.411 (4)	C14—C15	1.387 (4)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.408 (4)	C15—C16	1.389 (4)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.370 (4)	C16—C17	1.386 (4)
C7—H7	0.9500	C16—H16	0.9500
C8—N81	1.405 (3)	C17—C18	1.376 (4)
C8—C9	1.417 (4)	C17—H17	0.9500
C9—C10	1.417 (3)	C18—C19	1.395 (4)

C2—N1—C9	117.1 (2)	N12—N81—H81	115.7 (18)
N1—C2—C3	124.5 (3)	C8—N81—H81	111.5 (19)
N1—C2—H2	117.8	O11—C11—N12	124.7 (2)
C3—C2—H2	117.8	O11—C11—C18	130.1 (2)
C4—C3—C2	118.7 (3)	N12—C11—C18	105.3 (2)
C4—C3—H3	120.6	N81—N12—C13	124.3 (2)
C2—C3—H3	120.6	N81—N12—C11	123.5 (2)
C3—C4—C10	119.9 (3)	C13—N12—C11	112.0 (2)
C3—C4—H4	120.0	O13—C13—N12	123.9 (3)
C10—C4—H4	120.0	O13—C13—C19	130.4 (3)
C6—C5—C10	119.9 (3)	N12—C13—C19	105.6 (2)
C6—C5—H5	120.0	C19—C14—C15	117.9 (3)
C10—C5—H5	120.0	C19—C14—H14	121.1
C5—C6—C7	120.8 (3)	C15—C14—H14	121.1
C5—C6—H6	119.6	C14—C15—C16	120.8 (3)
C7—C6—H6	119.6	C14—C15—H15	119.6
C8—C7—C6	120.6 (2)	C16—C15—H15	119.6
C8—C7—H7	119.7	C15—C16—C17	121.3 (3)
C6—C7—H7	119.7	C15—C16—H16	119.3
C7—C8—N81	122.4 (2)	C17—C16—H16	119.3
C7—C8—C9	119.8 (2)	C18—C17—C16	117.5 (3)
N81—C8—C9	117.5 (2)	C18—C17—H17	121.2
N1—C9—C10	122.6 (2)	C16—C17—H17	121.2
N1—C9—C8	118.1 (2)	C17—C18—C19	121.3 (3)
C10—C9—C8	119.3 (2)	C17—C18—C11	129.8 (2)
C5—C10—C4	123.3 (3)	C19—C18—C11	108.9 (2)
C5—C10—C9	119.5 (2)	C14—C19—C18	121.2 (3)
C4—C10—C9	117.2 (2)	C14—C19—C13	130.7 (3)
N12—N81—C8	116.8 (2)	C18—C19—C13	108.2 (2)

C9—N1—C2—C3	1.8 (4)	C18—C11—N12—N81	−177.1 (2)
N1—C2—C3—C4	−1.2 (5)	O11—C11—N12—C13	178.1 (3)
C2—C3—C4—C10	0.0 (4)	C18—C11—N12—C13	−1.1 (3)
C10—C5—C6—C7	1.1 (4)	N81—N12—C13—O13	−2.5 (4)
C5—C6—C7—C8	−0.3 (4)	C11—N12—C13—O13	−178.4 (2)
C6—C7—C8—N81	−175.8 (2)	N81—N12—C13—C19	177.3 (2)
C6—C7—C8—C9	−0.8 (4)	C11—N12—C13—C19	1.4 (3)
C2—N1—C9—C10	−1.3 (4)	C19—C14—C15—C16	0.0 (4)
C2—N1—C9—C8	178.7 (2)	C14—C15—C16—C17	0.3 (4)
C7—C8—C9—N1	−178.9 (2)	C15—C16—C17—C18	−0.2 (4)
N81—C8—C9—N1	−3.7 (4)	C16—C17—C18—C19	−0.1 (4)
C7—C8—C9—C10	1.2 (4)	C16—C17—C18—C11	179.2 (3)
N81—C8—C9—C10	176.4 (2)	O11—C11—C18—C17	1.9 (5)
C6—C5—C10—C4	178.6 (2)	N12—C11—C18—C17	−179.0 (3)
C6—C5—C10—C9	−0.7 (4)	O11—C11—C18—C19	−178.7 (3)
C3—C4—C10—C5	−178.9 (3)	N12—C11—C18—C19	0.4 (3)
C3—C4—C10—C9	0.3 (4)	C15—C14—C19—C18	−0.4 (4)
N1—C9—C10—C5	179.6 (3)	C15—C14—C19—C13	−179.7 (3)
C8—C9—C10—C5	−0.4 (4)	C17—C18—C19—C14	0.4 (4)
N1—C9—C10—C4	0.3 (4)	C11—C18—C19—C14	−179.0 (2)
C8—C9—C10—C4	−179.7 (2)	C17—C18—C19—C13	179.9 (2)
C7—C8—N81—N12	−29.9 (4)	C11—C18—C19—C13	0.5 (3)
C9—C8—N81—N12	155.1 (2)	O13—C13—C19—C14	−1.9 (5)
C8—N81—N12—C13	−73.0 (3)	N12—C13—C19—C14	178.3 (3)
C8—N81—N12—C11	102.4 (3)	O13—C13—C19—C18	178.7 (3)
O11—C11—N12—N81	2.1 (4)	N12—C13—C19—C18	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N81—H81···O11ⁱ	0.90 (3)	2.50 (3)	3.081 (3)	123 (2)
N81—H81···N1	0.90 (3)	2.28 (3)	2.712 (3)	109 (2)
C17—H17···N1ⁱⁱ	0.95	2.39	3.316 (4)	166

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁N₃O₂
M_r	289.29
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	150
a, b, c (Å)	16.397 (3), 10.819 (2), 7.6737 (15)
V (Å³)	1361.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.12 × 0.04

Data collection
Diffractometer	Enraf Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.976, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8737, 1676, 1350
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.099, 1.18
No. of reflections	1676
No. of parameters	204
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.44

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N81—H81···O11ⁱ	0.90 (3)	2.50 (3)	3.081 (3)	123 (2)
N81—H81···N1	0.90 (3)	2.28 (3)	2.712 (3)	109 (2)
C17—H17···N1ⁱⁱ	0.95	2.39	3.316 (4)	166.2

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

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