Crystal structure of N-(2-(2-oxoindolin-4-yl)ethyl)-N-propylpropan-1-aminium tetraphenylborate, C40H45BN2O

Hazem A. Ghabbour; Abdulrahman Al-Majed; Obaid S. Alruqi; Gamal A. E. Mostafa

doi:10.1515/ncrs-2016-0007

Open Access Published by De Gruyter (O) April 12, 2016

Crystal structure of N-(2-(2-oxoindolin-4-yl)ethyl)-N-propylpropan-1-aminium tetraphenylborate, C₄₀H₄₅BN₂O

Hazem A. Ghabbour , Abdulrahman Al-Majed , Obaid S. Alruqi and Gamal A. E. Mostafa

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2016-0007

Abstract

C₄₀H₄₅BN₂O, monoclinic, P2₁/c (No. 14), a = 14.4148(6) Å, b = 16.7684(7) Å, c = 13.7178(5), β = 102.791(1)°, V = 3233.5(2) Å³, Z = 4, R_gt(F) = 0.0424, wR_ref(F²) = 0.1128, T = 100 K.

CCDC no.:: 1444752

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:	Colourless blocks size 0.57×0.25×0.23 mm
Wavelength:	Mo K_α radiation (0.71073 Å)
μ	0.7 cm⁻¹
Diffractometer, scan mode:	Bruker ApexII, φ and ω scans
2θ_max, completeness:	49.994°, >99 %
N(hkl)_measured, N(hkl)_unique, R_int:	31822, 5679, 0.0602
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 4344
N(param)_refined:	407
Programs:	SHELX [11], Bruker programs [12]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
B1	0.75591(13)	0.49037(12)	0.72637(14)	0.0172(4)
O1	0.64976(8)	0.40570(7)	0.28578(8)	0.0226(3)
N1	0.77405(9)	0.05203(8)	0.67722(10)	0.0178(3)
N2	0.52943(10)	0.36155(9)	0.35663(10)	0.0181(3)
C1	0.77478(13)	−0.17446(11)	0.63361(14)	0.0278(4)
H1A	0.7816	−0.2081	0.5772	0.042*
H1B	0.7143	−0.1865	0.6518	0.042*
H1C	0.8274	−0.1850	0.6909	0.042*
C2	0.77641(16)	−0.08713(11)	0.60396(15)	0.0362(5)
H2A	0.8396	−0.0735	0.5915	0.043*
H2B	0.7280	−0.0775	0.5417	0.043*
C3	0.75607(12)	−0.03578(10)	0.68633(13)	0.0208(4)
H3A	0.7955	−0.0549	0.7506	0.025*
H3B	0.6886	−0.0432	0.6892	0.025*
C4	0.87633(11)	0.07283(11)	0.68335(13)	0.0240(4)
H4A	0.8826	0.1316	0.6815	0.029*
H4B	0.8960	0.0508	0.6241	0.029*
C5	0.94260(12)	0.04132(12)	0.77689(13)	0.0294(4)
H5A	1.0080	0.0595	0.7775	0.035*
H5B	0.9425	−0.0177	0.7741	0.035*
C6	0.91705(14)	0.06715(12)	0.87365(14)	0.0353(5)
H6A	0.9685	0.0523	0.9303	0.053*
H6B	0.8580	0.0407	0.8801	0.053*
H6C	0.9081	0.1251	0.8731	0.053*
C7	0.70886(12)	0.08930(10)	0.58817(12)	0.0201(4)
H7A	0.6434	0.0689	0.5826	0.024*
H7B	0.7297	0.0741	0.5266	0.024*
C8	0.70888(11)	0.18043(10)	0.59741(13)	0.0212(4)
H8A	0.7246	0.1953	0.6690	0.025*
H8B	0.7588	0.2028	0.5661	0.025*
C9	0.61391(11)	0.21658(10)	0.54826(12)	0.0183(4)
C10	0.53076(11)	0.19616(10)	0.57997(12)	0.0202(4)
H10A	0.5340	0.1575	0.6313	0.024*
C11	0.44415(11)	0.23133(10)	0.53774(12)	0.0204(4)
H11A	0.3892	0.2162	0.5607	0.024*
C12	0.43590(11)	0.28817(10)	0.46253(12)	0.0178(4)
H12A	0.3767	0.3126	0.4338	0.021*
C13	0.51779(11)	0.30720(9)	0.43169(11)	0.0166(4)
C14	0.60579(11)	0.27268(10)	0.47293(12)	0.0163(4)
C15	0.67863(11)	0.30712(10)	0.42169(12)	0.0194(4)
H15A	0.7081	0.2650	0.3879	0.023*
H15B	0.7291	0.3356	0.4697	0.023*
C16	0.62077(11)	0.36404(10)	0.34682(12)	0.0180(4)
C17	0.93567(12)	0.33014(11)	0.65796(16)	0.0318(5)
H17A	0.9648	0.3191	0.6037	0.038*
C18	0.95644(12)	0.28317(11)	0.74296(16)	0.0350(5)
H18A	1.0007	0.2405	0.7483	0.042*
C19	0.91164(13)	0.29944(11)	0.81988(15)	0.0324(5)
H19A	0.9245	0.2674	0.8785	0.039*
C20	0.84792(12)	0.36236(11)	0.81190(13)	0.0250(4)
H20A	0.8174	0.3717	0.8655	0.030*
C21	0.82645(11)	0.41280(10)	0.72844(12)	0.0190(4)
C22	0.87226(11)	0.39350(10)	0.65159(13)	0.0228(4)
H22A	0.8595	0.4250	0.5926	0.027*
C23	0.72769(11)	0.52700(10)	0.61237(11)	0.0157(4)
C24	0.64354(11)	0.51030(10)	0.54204(12)	0.0169(4)
H24A	0.5981	0.4759	0.5608	0.020*
C25	0.62380(12)	0.54193(10)	0.44609(12)	0.0198(4)
H25A	0.5652	0.5297	0.4013	0.024*
C26	0.68872(12)	0.59098(10)	0.41547(12)	0.0201(4)
H26A	0.6754	0.6128	0.3499	0.024*
C27	0.77368(11)	0.60788(10)	0.48188(12)	0.0214(4)
H27A	0.8197	0.6406	0.4615	0.026*
C28	0.79163(11)	0.57717(10)	0.57789(12)	0.0202(4)
H28A	0.8499	0.5906	0.6225	0.024*
C29	0.81020(11)	0.56043(10)	0.80204(12)	0.0170(4)
C30	0.77297(12)	0.63812(10)	0.79610(12)	0.0220(4)
H30A	0.7175	0.6493	0.7461	0.026*
C31	0.81293(13)	0.69904(11)	0.85934(13)	0.0249(4)
H31A	0.7843	0.7504	0.8528	0.030*
C32	0.89480(12)	0.68545(10)	0.93252(12)	0.0226(4)
H32A	0.9230	0.7271	0.9761	0.027*
C33	0.93421(12)	0.61016(11)	0.94042(12)	0.0223(4)
H33A	0.9904	0.5998	0.9898	0.027*
C34	0.89252(11)	0.54931(10)	0.87686(12)	0.0197(4)
H34A	0.9211	0.4980	0.8845	0.024*
C35	0.66057(11)	0.46053(10)	0.76453(11)	0.0164(4)
C36	0.61816(11)	0.50384(10)	0.83018(12)	0.0199(4)
H36A	0.6429	0.5550	0.8517	0.024*
C37	0.54082(12)	0.47482(11)	0.86528(12)	0.0238(4)
H37A	0.5141	0.5062	0.9098	0.029*
C38	0.50299(12)	0.40098(11)	0.83585(13)	0.0250(4)
H38A	0.4516	0.3804	0.8612	0.030*
C39	0.54129(12)	0.35729(11)	0.76862(12)	0.0233(4)
H39A	0.5149	0.3069	0.7461	0.028*
C40	0.61785(11)	0.38670(10)	0.73413(12)	0.0197(4)
H40A	0.6426	0.3556	0.6879	0.024*
H1N2	0.4834(14)	0.3927(12)	0.3228(15)	0.035(6)*
H1N1	0.7547(13)	0.0746(12)	0.7338(15)	0.031(5)*

Source of material

To a solution of 4-[2-(dipropylamino) ethyl]-1,3-dihydro-2H-indol-2-one (0.26g, 1 mmol) in deionized water (25 mL) a solution of sodium tetraphenylborate (0.34 g, 1 mmol) in deionized water (25 mL) was added. A greenish precipitate was formed and filtered off, washed with cold water. The precipitate was dried under vacuum to give the title salt. Recrystallization from ethanol gave a yield of 74%.

Experimental details

All carbon-bound hydrogen atoms were placed in calculated positions. The coordinates and the U_iso values of the nitrogen-bound were refined freely.

Discussion

Ropinirole is a non-ergoline dopamine D2 receptor agonist, used to treat Parkinson's disease and restless leg syndrome [1–4]. Ropinirole is the first drug approved by the FDA for the treatment of the restless legs syndrome [5]. Sodium tetraphenylborate is used in inorganic and organometallic chemistry as a precipitating reagent [6]. It is also used for the formation of sensing material in polyvinyl chloride sensors [7–10].

In this study we report the synthesis and X-ray crystal structure of the tetraphenylborate salt of ropinirole. The packing in the crystal structure is stabilized via one intermolecular classical hydrogen bond, of which O1 work as hydrogen bond acceptor and N1 work as hydrogen bond donor. The distance of the interaction between N1—N1H1⋯O1ⁱ is 1.839(19) Å, and the angle is 142.8(17) Å. Symmetry codes: (i) x, −y+1/2, z+1/2. All bond lengths and angles are in the normal ranges.

Funding source: King Saud University

Award Identifier / Grant number: RG-1436–024

Funding statement: The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project no. RG-1436–024.

Acknowledgements:

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project no. RG-1436–024.

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Received: 2016-1-3

Accepted: 2016-3-10

Published Online: 2016-4-12

Published in Print: 2016-9-1

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.