1-(12-Bromo­dodec­yl)-5-chloro­indoline-2,3-dione

Tribak, Z.; Kandri Rodi, Y.; Haoudi, A.; Essassi, E.M.; Capet, F.; Zouihri, H.

doi:10.1107/S2414314616009718

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160971

doi:10.1107/S2414314616009718

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1-(12-Bromododecyl)-5-chloroindoline-2,3-dione

Zineb Tribak,^a Youssef Kandri Rodi,^a Amal Haoudi,^a ^* El Mokhtar Essassi,^b Fréderic Capet ^c and Hafid Zouihri ^d

^aLaboratoire de Chimie Organique Appliquée-Chimie Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, ^cUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France, and ^dDépartement de Chimie, Faculté des Sciences, Université Ibn Zohr, BP 8106, Cité Dakhla, 80000 Agadir, Morocco
^*Correspondence e-mail: haoudi_amal@yahoo.fr

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 26 May 2016; accepted 15 June 2016; online 21 June 2016)

In the structure of the title compound, C₂₀H₂₇BrClNO₂, the 5-chloroindoline-2,3-dione ring system is approximately planar, the largest deviation from the mean plane being 0.0237 (10) Å. The mean plane through the fused-ring system makes a dihedral angle of 61.00 (18)° with the mean plane passing through the 1-dodecyl chain. All C atoms of the dodecyl group adopt the planar zigzag arrangement normally observed in n-alkane compounds. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains parallel to the b axis.

Keywords: crystal structure; chloroindoline-2,3-dione; chains; hydrogen bonds.

CCDC reference: 1485734

Structure description

5-Chloroisatin is a versatile chemical, able to participate in a wide variety of synthetic reactions and form a large number of heterocyclic molecules (Abele et al., 2003 ) and has an indoline ring structure (Adibi et al.,2010 ). 5-Chloroisatin derivatives possess a wide range of biological activities (Bhrigu et al., 2010 ; Cerchiaro et al., 2006 ; Chaluvaraju et al., 2011 ; Chen et al., 2011 ; Chibale et al., 2005 ). The title compound (Fig. 1) was obtained by the reaction of 1,12-dibromododecane with 5-chloroisatin under phase-transfer catalysis conditions.

Figure 1
The molecular structure of the title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

The 5-chloroindoline-2,3-dione ring system is approximately planar, the largest deviation from the mean plane being 0.0237 (10) A°. The mean plane through the fused-ring system makes a dihedral angle of 61.00 (18)° with the mean plane passing through the 1-dodecyl chain. All C atoms of the dodecyl group adopt the planar zigzag arrangement normally observed in n-alkane compounds. In the crystal, molecules are linked by C—H⋯O hydrogen bonds (Table 1, Fig. 2), forming chains parallel to the b axis.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.55	3.406 (3)	153
Symmetry code: (i) x, y-1, z.

Figure 2
The crystal structure of the title compound, viewed along the a axis, showing chains parallel to the b axis linked by C— H⋯O hydrogen bonds (dashed lines).

Synthesis and crystallization

To a solution of 5-chloro-1H-indole-2,3-dione (0.4 g, 2.20 mmol) in N,N-dimethylformamide (25 ml) was added potassium carbonate (0.5 g, 3.3 mmol), n-butylammoium bromide (0.1 g, 0.3 mmol) and 1,12-dibromododecane (0.79 g, 2.42 mmol). The reaction mixture was stirred at 25°C for 48 h. The reaction was monitored by TLC and the resulting mixture was filtered. The title compound was recrystallized from ethanol to afford orange crystals (m.p. 348 K, yield 83%)

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₂₇BrClNO₂
M_r	428.78
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.0353 (4), 8.3496 (5), 17.1096 (11)
α, β, γ (°)	84.491 (3), 78.086 (3), 65.126 (2)
V (Å³)	1018.94 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.16
Crystal size (mm)	0.43 × 0.42 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.616, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	27898, 4137, 3048
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.04
No. of reflections	4137
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.75
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1485734

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616009718/ff4007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009718/ff4007Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009718/ff4007Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

1-(12-Bromododecyl)-5-chloroindoline-2,3-dione top

Crystal data top

C₂₀H₂₇BrClNO₂	Z = 2
M_r = 428.78	F(000) = 444
Triclinic, P1	D_x = 1.398 Mg m⁻³
a = 8.0353 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3496 (5) Å	Cell parameters from 8944 reflections
c = 17.1096 (11) Å	θ = 2.4–26.1°
α = 84.491 (3)°	µ = 2.16 mm⁻¹
β = 78.086 (3)°	T = 296 K
γ = 65.126 (2)°	Plate, orange
V = 1018.94 (10) Å³	0.43 × 0.42 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	3048 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θ_max = 26.4°, θ_min = 2.4°
T_min = 0.616, T_max = 0.745	h = −10→9
27898 measured reflections	k = −10→10
4137 independent reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0487P)² + 0.8854P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4137 reflections	Δρ_max = 0.80 e Å⁻³
226 parameters	Δρ_min = −0.75 e Å⁻³
0 restraints

Special details top

Experimental. SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0808 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8269. The λ/2 correction factor is 0.00150.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Br1	−0.24071 (6)	0.15532 (6)	0.28981 (3)	0.08347 (19)
Cl1	0.46586 (13)	0.04747 (11)	1.16822 (5)	0.0638 (2)
O1	0.6524 (3)	0.6434 (3)	1.07775 (13)	0.0531 (5)
O2	0.9025 (3)	0.6153 (3)	0.92241 (14)	0.0551 (5)
N1	0.8799 (3)	0.3488 (3)	0.92033 (13)	0.0392 (5)
C1	0.7886 (3)	0.2574 (3)	0.97305 (15)	0.0337 (6)
C6	0.6863 (3)	0.3557 (3)	1.04153 (15)	0.0335 (6)
C7	0.7132 (4)	0.5205 (3)	1.03357 (17)	0.0374 (6)
C2	0.7910 (4)	0.0933 (3)	0.96406 (16)	0.0377 (6)
H2	0.8583	0.0266	0.9186	0.045*
C8	0.8440 (4)	0.5069 (4)	0.95180 (17)	0.0411 (6)
C5	0.5856 (4)	0.2953 (3)	1.10186 (16)	0.0377 (6)
H5	0.5179	0.3617	1.1474	0.045*
C3	0.6898 (4)	0.0324 (3)	1.02514 (18)	0.0432 (7)
H3	0.6900	−0.0779	1.0207	0.052*
C4	0.5887 (4)	0.1309 (4)	1.09226 (17)	0.0399 (6)
C11	0.7731 (4)	0.2822 (4)	0.76445 (17)	0.0452 (7)
H11A	0.6701	0.3224	0.8094	0.054*
H11B	0.8299	0.1542	0.7662	0.054*
C9	1.0082 (4)	0.2821 (4)	0.84536 (18)	0.0486 (7)
H9A	1.0593	0.1541	0.8464	0.058*
H9B	1.1110	0.3168	0.8405	0.058*
C12	0.6981 (5)	0.3432 (4)	0.68750 (18)	0.0525 (7)
H12A	0.6394	0.4712	0.6868	0.063*
H12B	0.8024	0.3062	0.6430	0.063*
C10	0.9151 (4)	0.3500 (4)	0.77284 (18)	0.0512 (7)
H10A	0.8544	0.4778	0.7750	0.061*
H10B	1.0114	0.3187	0.7252	0.061*
C13	0.5587 (5)	0.2750 (4)	0.67480 (18)	0.0530 (8)
H13A	0.4476	0.3236	0.7155	0.064*
H13B	0.6117	0.1476	0.6816	0.064*
C14	0.5031 (5)	0.3204 (5)	0.59322 (18)	0.0543 (8)
H14A	0.4482	0.4478	0.5870	0.065*
H14B	0.6149	0.2740	0.5526	0.065*
C16	0.3166 (5)	0.2901 (5)	0.49670 (19)	0.0567 (8)
H16A	0.2639	0.4170	0.4886	0.068*
H16B	0.4301	0.2402	0.4573	0.068*
C15	0.3668 (5)	0.2501 (5)	0.57882 (19)	0.0575 (8)
H15A	0.4199	0.1231	0.5869	0.069*
H15B	0.2533	0.2998	0.6183	0.069*
C17	0.1805 (5)	0.2208 (5)	0.4821 (2)	0.0601 (8)
H17A	0.0674	0.2696	0.5218	0.072*
H17B	0.2337	0.0936	0.4894	0.072*
C18	0.1295 (5)	0.2636 (5)	0.3997 (2)	0.0609 (9)
H18A	0.0780	0.3907	0.3919	0.073*
H18B	0.2422	0.2130	0.3599	0.073*
C19	−0.0096 (5)	0.1958 (5)	0.3862 (2)	0.0625 (9)
H19A	0.0436	0.0682	0.3917	0.075*
H19B	−0.1209	0.2429	0.4271	0.075*
C20	−0.0632 (6)	0.2455 (5)	0.3059 (2)	0.0700 (10)
H20A	0.0479	0.1991	0.2649	0.084*
H20B	−0.1177	0.3731	0.3005	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0751 (3)	0.0929 (3)	0.0933 (3)	−0.0366 (2)	−0.0263 (2)	−0.0176 (2)
Cl1	0.0758 (6)	0.0589 (5)	0.0656 (5)	−0.0440 (4)	−0.0036 (4)	0.0151 (4)
O1	0.0619 (13)	0.0357 (11)	0.0673 (14)	−0.0256 (10)	−0.0081 (11)	−0.0090 (10)
O2	0.0585 (13)	0.0484 (12)	0.0700 (15)	−0.0354 (11)	−0.0134 (11)	0.0139 (10)
N1	0.0433 (13)	0.0407 (13)	0.0392 (13)	−0.0229 (10)	−0.0080 (10)	0.0020 (10)
C1	0.0341 (13)	0.0316 (13)	0.0392 (15)	−0.0144 (11)	−0.0154 (11)	0.0056 (11)
C6	0.0374 (13)	0.0272 (13)	0.0409 (15)	−0.0152 (11)	−0.0142 (11)	0.0012 (11)
C7	0.0382 (14)	0.0310 (14)	0.0489 (16)	−0.0170 (11)	−0.0158 (12)	0.0022 (12)
C2	0.0430 (15)	0.0310 (14)	0.0421 (15)	−0.0154 (12)	−0.0124 (12)	−0.0034 (11)
C8	0.0418 (15)	0.0376 (15)	0.0513 (17)	−0.0209 (12)	−0.0177 (13)	0.0079 (12)
C5	0.0411 (14)	0.0346 (14)	0.0388 (15)	−0.0164 (11)	−0.0096 (11)	0.0025 (11)
C3	0.0506 (16)	0.0286 (14)	0.0595 (18)	−0.0209 (12)	−0.0218 (14)	0.0046 (12)
C4	0.0445 (15)	0.0361 (15)	0.0457 (16)	−0.0226 (12)	−0.0142 (12)	0.0104 (12)
C11	0.0473 (16)	0.0474 (17)	0.0399 (16)	−0.0205 (13)	−0.0051 (12)	0.0023 (13)
C9	0.0397 (15)	0.0605 (19)	0.0482 (17)	−0.0255 (14)	−0.0020 (13)	−0.0023 (14)
C12	0.0617 (19)	0.060 (2)	0.0405 (17)	−0.0309 (16)	−0.0104 (14)	0.0073 (14)
C10	0.0535 (18)	0.062 (2)	0.0417 (17)	−0.0306 (16)	−0.0037 (14)	0.0031 (14)
C13	0.0595 (19)	0.061 (2)	0.0427 (17)	−0.0304 (16)	−0.0110 (14)	0.0101 (14)
C14	0.065 (2)	0.066 (2)	0.0404 (17)	−0.0354 (17)	−0.0099 (14)	0.0066 (15)
C16	0.067 (2)	0.067 (2)	0.0449 (18)	−0.0368 (18)	−0.0095 (15)	0.0025 (15)
C15	0.062 (2)	0.071 (2)	0.0458 (18)	−0.0358 (18)	−0.0109 (15)	0.0077 (16)
C17	0.063 (2)	0.069 (2)	0.055 (2)	−0.0340 (18)	−0.0134 (16)	0.0025 (16)
C18	0.070 (2)	0.068 (2)	0.053 (2)	−0.0356 (18)	−0.0121 (16)	−0.0028 (16)
C19	0.064 (2)	0.064 (2)	0.065 (2)	−0.0295 (18)	−0.0144 (17)	−0.0034 (17)
C20	0.076 (2)	0.078 (3)	0.069 (2)	−0.042 (2)	−0.0148 (19)	−0.0072 (19)

Geometric parameters (Å, º) top

Br1—C20	1.945 (4)	C12—C13	1.512 (4)
Cl1—C4	1.738 (3)	C10—H10A	0.9700
O1—C7	1.199 (3)	C10—H10B	0.9700
O2—C8	1.210 (3)	C13—H13A	0.9700
N1—C1	1.415 (3)	C13—H13B	0.9700
N1—C8	1.367 (4)	C13—C14	1.518 (4)
N1—C9	1.458 (4)	C14—H14A	0.9700
C1—C6	1.394 (4)	C14—H14B	0.9700
C1—C2	1.385 (3)	C14—C15	1.512 (4)
C6—C7	1.470 (3)	C16—H16A	0.9700
C6—C5	1.369 (4)	C16—H16B	0.9700
C7—C8	1.549 (4)	C16—C15	1.510 (4)
C2—H2	0.9300	C16—C17	1.505 (5)
C2—C3	1.381 (4)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C5—C4	1.388 (4)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C3—C4	1.375 (4)	C17—C18	1.517 (5)
C11—H11A	0.9700	C18—H18A	0.9700
C11—H11B	0.9700	C18—H18B	0.9700
C11—C12	1.515 (4)	C18—C19	1.512 (5)
C11—C10	1.507 (4)	C19—H19A	0.9700
C9—H9A	0.9700	C19—H19B	0.9700
C9—H9B	0.9700	C19—C20	1.494 (5)
C9—C10	1.520 (4)	C20—H20A	0.9700
C12—H12A	0.9700	C20—H20B	0.9700
C12—H12B	0.9700

C1—N1—C9	126.1 (2)	H10A—C10—H10B	107.4
C8—N1—C1	110.8 (2)	C12—C13—H13A	108.8
C8—N1—C9	123.0 (2)	C12—C13—H13B	108.8
C6—C1—N1	110.7 (2)	C12—C13—C14	113.8 (3)
C2—C1—N1	128.9 (2)	H13A—C13—H13B	107.7
C2—C1—C6	120.4 (2)	C14—C13—H13A	108.8
C1—C6—C7	107.4 (2)	C14—C13—H13B	108.8
C5—C6—C1	121.9 (2)	C13—C14—H14A	108.6
C5—C6—C7	130.7 (2)	C13—C14—H14B	108.6
O1—C7—C6	130.6 (3)	H14A—C14—H14B	107.6
O1—C7—C8	124.5 (2)	C15—C14—C13	114.6 (3)
C6—C7—C8	104.9 (2)	C15—C14—H14A	108.6
C1—C2—H2	121.2	C15—C14—H14B	108.6
C3—C2—C1	117.6 (3)	H16A—C16—H16B	107.5
C3—C2—H2	121.2	C15—C16—H16A	108.6
O2—C8—N1	127.4 (3)	C15—C16—H16B	108.6
O2—C8—C7	126.4 (3)	C17—C16—H16A	108.6
N1—C8—C7	106.2 (2)	C17—C16—H16B	108.6
C6—C5—H5	121.4	C17—C16—C15	114.8 (3)
C6—C5—C4	117.3 (3)	C14—C15—H15A	108.6
C4—C5—H5	121.4	C14—C15—H15B	108.6
C2—C3—H3	119.2	C16—C15—C14	114.5 (3)
C4—C3—C2	121.5 (2)	C16—C15—H15A	108.6
C4—C3—H3	119.2	C16—C15—H15B	108.6
C5—C4—Cl1	118.8 (2)	H15A—C15—H15B	107.6
C3—C4—Cl1	119.9 (2)	C16—C17—H17A	108.7
C3—C4—C5	121.3 (3)	C16—C17—H17B	108.7
H11A—C11—H11B	107.8	C16—C17—C18	114.3 (3)
C12—C11—H11A	109.1	H17A—C17—H17B	107.6
C12—C11—H11B	109.1	C18—C17—H17A	108.7
C10—C11—H11A	109.1	C18—C17—H17B	108.7
C10—C11—H11B	109.1	C17—C18—H18A	108.8
C10—C11—C12	112.7 (2)	C17—C18—H18B	108.8
N1—C9—H9A	109.0	H18A—C18—H18B	107.7
N1—C9—H9B	109.0	C19—C18—C17	113.7 (3)
N1—C9—C10	112.7 (2)	C19—C18—H18A	108.8
H9A—C9—H9B	107.8	C19—C18—H18B	108.8
C10—C9—H9A	109.0	C18—C19—H19A	109.0
C10—C9—H9B	109.0	C18—C19—H19B	109.0
C11—C12—H12A	108.5	H19A—C19—H19B	107.8
C11—C12—H12B	108.5	C20—C19—C18	112.7 (3)
H12A—C12—H12B	107.5	C20—C19—H19A	109.0
C13—C12—C11	115.0 (2)	C20—C19—H19B	109.0
C13—C12—H12A	108.5	Br1—C20—H20A	109.2
C13—C12—H12B	108.5	Br1—C20—H20B	109.2
C11—C10—C9	115.6 (2)	C19—C20—Br1	111.9 (3)
C11—C10—H10A	108.4	C19—C20—H20A	109.2
C11—C10—H10B	108.4	C19—C20—H20B	109.2
C9—C10—H10A	108.4	H20A—C20—H20B	107.9
C9—C10—H10B	108.4

O1—C7—C8—O2	0.6 (4)	C2—C3—C4—Cl1	−179.1 (2)
O1—C7—C8—N1	−179.6 (3)	C2—C3—C4—C5	−0.7 (4)
N1—C1—C6—C7	−0.4 (3)	C8—N1—C1—C6	0.7 (3)
N1—C1—C6—C5	−179.9 (2)	C8—N1—C1—C2	−179.1 (3)
N1—C1—C2—C3	179.6 (2)	C8—N1—C9—C10	−86.0 (3)
N1—C9—C10—C11	−68.4 (4)	C5—C6—C7—O1	−0.6 (5)
C1—N1—C8—O2	179.1 (3)	C5—C6—C7—C8	179.4 (3)
C1—N1—C8—C7	−0.7 (3)	C11—C12—C13—C14	−173.3 (3)
C1—N1—C9—C10	99.3 (3)	C9—N1—C1—C6	175.9 (2)
C1—C6—C7—O1	−179.9 (3)	C9—N1—C1—C2	−3.9 (4)
C1—C6—C7—C8	0.0 (3)	C9—N1—C8—O2	3.7 (4)
C1—C6—C5—C4	−0.1 (4)	C9—N1—C8—C7	−176.1 (2)
C1—C2—C3—C4	0.5 (4)	C12—C11—C10—C9	−175.2 (3)
C6—C1—C2—C3	−0.2 (4)	C12—C13—C14—C15	178.8 (3)
C6—C7—C8—O2	−179.3 (3)	C10—C11—C12—C13	178.4 (3)
C6—C7—C8—N1	0.4 (3)	C13—C14—C15—C16	−178.0 (3)
C6—C5—C4—Cl1	178.9 (2)	C16—C17—C18—C19	−179.1 (3)
C6—C5—C4—C3	0.4 (4)	C15—C16—C17—C18	179.3 (3)
C7—C6—C5—C4	−179.4 (3)	C17—C16—C15—C14	−179.9 (3)
C2—C1—C6—C7	179.4 (2)	C17—C18—C19—C20	177.8 (3)
C2—C1—C6—C5	0.0 (4)	C18—C19—C20—Br1	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.55	3.406 (3)	153

Symmetry code: (i) x, y−1, z.

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