1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetra­hydro­quinolin-2-yl]thio­urea

Asiri, A.M.; Faidallah, H.M.; Al-Youbi, A.O.; Alamry, K.A.; Ng, S.W.

doi:10.1107/S1600536811033046

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2430

doi:10.1107/S1600536811033046

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1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]thiourea

Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Abdulrahman O. Al-Youbi,^a Khalid A. Alamry ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 August 2011; accepted 15 August 2011; online 27 August 2011)

In the N-substituted benzoylthiourea, C₂₄H₂₃N₅OS, the benzoylthiourea unit is non-planar (r.m.s. deviation = 0.126 Å). The aliphatic part of the tetrahydroquinoline fused-ring system is disordered over two positions in a 0.592 (5):0.408 (5) ratio. The pyridine and pyrrole rings are twisted by 55.2 (1)° in order to avoid crowding of their respective substituents. Pairs of molecules are linked by N—H⋯N hydrogen bonds, forming centrosymmetric dimers. Furthermore, an intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation.

Related literature

For medicinal properties of cyanopyridines, see: Cocco et al. (2005 ); El-Hawash et al. (2006 ).

Experimental

Crystal data

C₂₄H₂₃N₅OS
M_r = 429.53
Triclinic, $[P \overline 1]$
a = 9.7072 (4) Å
b = 10.4928 (5) Å
c = 11.8828 (5) Å
α = 82.245 (4)°
β = 84.263 (3)°
γ = 63.671 (4)°
V = 1073.76 (8) Å³
Z = 2
Cu Kα radiation
μ = 1.55 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.654, T_max = 0.747
7386 measured reflections
4218 independent reflections
3897 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.146
S = 1.03
4218 reflections
294 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1	0.88	1.90	2.594 (2)	135
N5—H5⋯N3ⁱ	0.88	2.22	3.058 (2)	158
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033046/bt5613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033046/bt5613Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033046/bt5613Isup3.cml

checkCIF report

Comment top

There are several studies on cyanopyridine derivatives as these compounds exhibit useful anticancer and antiviral activities Cocco et al., 2005; El-Hawash et al., 2006). If these compounds possess a primary amine group, then they can be reacted with phenyl isothiocyanate to yield cyanopyridine-benzoythiourea derivatives, yet another class of medicinal compounds. Because of the ease phenyl isothiocyanate reacts with primary amines, we have in this study used 2-amino-3-cyano–8-methyl-4-(N-methylpyrrolyl)-5,6,7,8-tetrahydroquinoline to synthesize the correponding N-substituted benzoylthiourea (Scheme I).

In the N-substituted benzoylthiourea, C₂₄H₂₃N₅OS, the benzoylthiourea portion is somewhat non-planar; the mean plane is aligned at 67.9 (1)° with respect the the mean-plane of the non-planar tetrahydroquinoline fused-ring. An intramolecular N–H···O hydrogen bond appears to prevent further twisting in the benzoylthiourea portion. The aliphatic portion of the tetrahydroquinoline fused-ring is disordered over two positions in a 0.592 (5): 0.408 ratio. The pyridine ring (which has a cyanide substituent) and the pyrrole ring (which has a methyl substitutent) are twisted by 55.2 (1) ° in order to avoid crowding of their respective substituents (Fig. 1). Two molecules are linked by an N–H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).

Related literature top

For medicinal properties of cyanopyridines, see: Cocco et al. (2005); El-Hawash et al. (2006).

Experimental top

2-Amino-3-cyano–8-methyl-4-(N-methylpyrrolyl)-5,6,7,8-tetrahydroquinoline (10 mmol), potassium carbonate (20 mmol) in dry acetone (25 ml) was stirred and then treated with phenyl isothiocyanate (12 mmol). The mixture was heated for 10 h; the acetone was removed under pressure and the solid mass dissolved in water. The solution was acidified with 2 N hydrochloric acid. The crude product was purified by recrystallization from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₄H₂₃N₅OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the cyclohexene ring is not shown.

1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)- 5,6,7,8-tetrahydroquinolin-2-yl]thiourea top

Crystal data top

C₂₄H₂₃N₅OS	Z = 2
M_r = 429.53	F(000) = 452
Triclinic, P1	D_x = 1.329 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7072 (4) Å	Cell parameters from 4274 reflections
b = 10.4928 (5) Å	θ = 3.8–74.2°
c = 11.8828 (5) Å	µ = 1.55 mm⁻¹
α = 82.245 (4)°	T = 100 K
β = 84.263 (3)°	Prism, brown–orange
γ = 63.671 (4)°	0.30 × 0.20 × 0.20 mm
V = 1073.76 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4218 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3897 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.020
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.3°, θ_min = 3.8°
ω scans	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→13
T_min = 0.654, T_max = 0.747	l = −14→14
7386 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0825P)² + 0.7756P] where P = (F_o² + 2F_c²)/3
4218 reflections	(Δ/σ)_max = 0.001
294 parameters	Δρ_max = 1.25 e Å⁻³
20 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₄H₂₃N₅OS	γ = 63.671 (4)°
M_r = 429.53	V = 1073.76 (8) Å³
Triclinic, P1	Z = 2
a = 9.7072 (4) Å	Cu Kα radiation
b = 10.4928 (5) Å	µ = 1.55 mm⁻¹
c = 11.8828 (5) Å	T = 100 K
α = 82.245 (4)°	0.30 × 0.20 × 0.20 mm
β = 84.263 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4218 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3897 reflections with I > 2σ(I)
T_min = 0.654, T_max = 0.747	R_int = 0.020
7386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	20 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 1.25 e Å⁻³
4218 reflections	Δρ_min = −0.46 e Å⁻³
294 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.25749 (6)	0.66030 (6)	0.41290 (5)	0.03749 (18)
O1	0.63636 (17)	0.62389 (15)	0.14578 (12)	0.0305 (3)
N1	0.2933 (2)	1.01329 (17)	0.24918 (14)	0.0344 (4)
N2	0.16227 (18)	1.03258 (17)	0.67653 (13)	0.0251 (3)
N3	0.49398 (19)	0.73393 (17)	0.59776 (13)	0.0270 (4)
N4	0.43635 (19)	0.77111 (16)	0.29593 (13)	0.0240 (3)
H4	0.5199	0.7558	0.2524	0.029*
N5	0.48814 (18)	0.54112 (16)	0.26536 (13)	0.0235 (3)
H5	0.4773	0.4630	0.2898	0.028*
C1	0.2196 (5)	1.2331 (4)	0.0699 (3)	0.0388 (8)	0.592 (5)
H1A	0.1607	1.3010	0.0078	0.058*	0.592 (5)
H1B	0.2515	1.1353	0.0516	0.058*	0.592 (5)
H1C	0.3109	1.2470	0.0796	0.058*	0.592 (5)
C2	0.1198 (4)	1.2577 (3)	0.1793 (3)	0.0238 (7)	0.592 (5)
H2	0.0328	1.2349	0.1681	0.029*	0.592 (5)
C3	0.0504 (4)	1.4093 (4)	0.2080 (4)	0.0286 (11)	0.592 (5)
H3A	−0.0277	1.4696	0.1520	0.034*	0.592 (5)
H3B	0.1320	1.4426	0.1998	0.034*	0.592 (5)
C4	−0.0245 (11)	1.4323 (12)	0.3259 (5)	0.0466 (10)	0.592 (5)
H4A	−0.1133	1.4088	0.3331	0.056*	0.592 (5)
H4B	−0.0628	1.5339	0.3389	0.056*	0.592 (5)
C1'	0.1144 (7)	1.2261 (6)	0.0836 (4)	0.0388 (8)	0.408
H1'A	0.0981	1.2943	0.0155	0.058*	0.408 (5)
H1'B	0.0150	1.2317	0.1156	0.058*	0.408 (5)
H1'C	0.1799	1.1291	0.0633	0.058*	0.408 (5)
C2'	0.1916 (6)	1.2618 (5)	0.1706 (4)	0.0238 (7)	0.408
H2'	0.2952	1.2502	0.1384	0.029*	0.408 (5)
C3'	0.1035 (7)	1.4112 (6)	0.2064 (5)	0.0286 (11)	0.408
H3'1	0.1780	1.4469	0.2214	0.034*	0.408 (5)
H3'2	0.0414	1.4746	0.1426	0.034*	0.408 (5)
C4'	−0.0017 (15)	1.4211 (19)	0.3106 (6)	0.0466 (10)	0.408
H4'1	−0.0741	1.3818	0.2978	0.056*	0.408 (5)
H4'2	−0.0628	1.5225	0.3244	0.056*	0.408 (5)
C5	0.0917 (2)	1.3376 (2)	0.41467 (16)	0.0295 (4)
H5A	0.1619	1.3809	0.4228	0.035*	0.592 (5)
H5B	0.0354	1.3367	0.4888	0.035*	0.592 (5)
H5C	0.1599	1.3801	0.4302	0.035*	0.408 (5)
H5D	0.0233	1.3403	0.4829	0.035*	0.408 (5)
C6	0.1874 (2)	1.18481 (19)	0.38818 (16)	0.0255 (4)
C7	0.2144 (3)	1.1494 (2)	0.27625 (16)	0.0357 (5)
C8	0.2487 (2)	1.07401 (19)	0.47547 (15)	0.0217 (4)
C9	0.3370 (2)	0.93424 (19)	0.44573 (15)	0.0223 (4)
C10	0.3513 (2)	0.90956 (19)	0.33176 (16)	0.0249 (4)
C11	0.2239 (2)	1.10237 (18)	0.59522 (15)	0.0220 (4)
C12	0.2572 (2)	1.1937 (2)	0.64847 (16)	0.0253 (4)
H12	0.3007	1.2552	0.6133	0.030*
C13	0.2148 (2)	1.1790 (2)	0.76492 (16)	0.0298 (4)
H13	0.2259	1.2276	0.8228	0.036*
C14	0.1548 (2)	1.0819 (2)	0.77873 (16)	0.0291 (4)
H14	0.1143	1.0532	0.8484	0.035*
C15	0.0892 (2)	0.9433 (2)	0.65744 (19)	0.0334 (5)
H15A	0.1105	0.8670	0.7200	0.050*
H15B	0.1301	0.9011	0.5856	0.050*
H15C	−0.0221	1.0016	0.6538	0.050*
C16	0.4215 (2)	0.82116 (19)	0.53048 (15)	0.0225 (4)
C17	0.3993 (2)	0.66125 (19)	0.32327 (16)	0.0244 (4)
C18	0.5910 (2)	0.53169 (19)	0.17416 (15)	0.0233 (4)
C19	0.6415 (2)	0.40659 (19)	0.10662 (15)	0.0244 (4)
C20	0.7465 (3)	0.4002 (2)	0.01627 (18)	0.0352 (5)
H20	0.7870	0.4686	0.0045	0.042*
C21	0.7924 (3)	0.2941 (2)	−0.05700 (19)	0.0416 (6)
H21	0.8637	0.2905	−0.1189	0.050*
C22	0.7342 (3)	0.1942 (2)	−0.03949 (18)	0.0371 (5)
H22	0.7655	0.1217	−0.0893	0.045*
C23	0.6301 (3)	0.1997 (2)	0.05058 (18)	0.0334 (5)
H23	0.5905	0.1306	0.0625	0.040*
C24	0.5832 (2)	0.3061 (2)	0.12401 (16)	0.0281 (4)
H24	0.5116	0.3097	0.1856	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0378 (3)	0.0290 (3)	0.0459 (3)	−0.0144 (2)	0.0180 (2)	−0.0197 (2)
O1	0.0407 (8)	0.0228 (7)	0.0261 (7)	−0.0125 (6)	0.0078 (6)	−0.0084 (5)
N1	0.0571 (11)	0.0163 (8)	0.0187 (8)	−0.0045 (8)	−0.0059 (7)	−0.0047 (6)
N2	0.0255 (8)	0.0218 (8)	0.0216 (8)	−0.0050 (6)	0.0024 (6)	−0.0033 (6)
N3	0.0295 (8)	0.0211 (8)	0.0220 (8)	−0.0038 (7)	0.0016 (6)	−0.0031 (6)
N4	0.0301 (8)	0.0163 (7)	0.0192 (7)	−0.0036 (6)	0.0019 (6)	−0.0063 (6)
N5	0.0296 (8)	0.0146 (7)	0.0213 (8)	−0.0047 (6)	0.0022 (6)	−0.0057 (6)
C1	0.055 (2)	0.0305 (15)	0.0249 (14)	−0.0156 (15)	−0.0034 (14)	0.0055 (11)
C2	0.028 (2)	0.0185 (11)	0.0216 (12)	−0.0078 (15)	−0.0025 (14)	−0.0007 (9)
C3	0.027 (3)	0.0208 (11)	0.0229 (11)	0.0015 (16)	0.0031 (17)	0.0022 (8)
C4	0.057 (3)	0.026 (2)	0.0306 (18)	0.0067 (18)	−0.0013 (17)	−0.0077 (17)
C1'	0.055 (2)	0.0305 (15)	0.0249 (14)	−0.0156 (15)	−0.0034 (14)	0.0055 (11)
C2'	0.028 (2)	0.0185 (11)	0.0216 (12)	−0.0078 (15)	−0.0025 (14)	−0.0007 (9)
C3'	0.027 (3)	0.0208 (11)	0.0229 (11)	0.0015 (16)	0.0031 (17)	0.0022 (8)
C4'	0.057 (3)	0.026 (2)	0.0306 (18)	0.0067 (18)	−0.0013 (17)	−0.0077 (17)
C5	0.0386 (11)	0.0161 (9)	0.0231 (9)	−0.0013 (8)	−0.0022 (8)	−0.0050 (7)
C6	0.0326 (10)	0.0163 (9)	0.0215 (9)	−0.0041 (7)	−0.0028 (7)	−0.0050 (7)
C7	0.0585 (14)	0.0157 (9)	0.0199 (9)	−0.0030 (9)	−0.0064 (9)	−0.0036 (7)
C8	0.0233 (8)	0.0188 (9)	0.0193 (9)	−0.0050 (7)	−0.0004 (7)	−0.0049 (7)
C9	0.0247 (9)	0.0173 (9)	0.0196 (9)	−0.0042 (7)	−0.0002 (7)	−0.0032 (7)
C10	0.0317 (10)	0.0166 (9)	0.0212 (9)	−0.0047 (7)	−0.0009 (7)	−0.0056 (7)
C11	0.0225 (8)	0.0165 (8)	0.0189 (8)	−0.0014 (7)	0.0013 (6)	−0.0030 (6)
C12	0.0300 (9)	0.0189 (9)	0.0208 (9)	−0.0045 (7)	0.0022 (7)	−0.0068 (7)
C13	0.0363 (10)	0.0239 (10)	0.0196 (9)	−0.0034 (8)	0.0000 (7)	−0.0073 (7)
C14	0.0314 (10)	0.0279 (10)	0.0172 (9)	−0.0038 (8)	0.0042 (7)	−0.0036 (7)
C15	0.0312 (10)	0.0335 (11)	0.0349 (11)	−0.0145 (9)	0.0041 (8)	−0.0043 (9)
C16	0.0246 (9)	0.0182 (9)	0.0193 (8)	−0.0043 (7)	0.0048 (7)	−0.0070 (7)
C17	0.0282 (9)	0.0169 (9)	0.0214 (9)	−0.0029 (7)	−0.0008 (7)	−0.0059 (7)
C18	0.0274 (9)	0.0168 (8)	0.0191 (8)	−0.0030 (7)	−0.0018 (7)	−0.0043 (7)
C19	0.0284 (9)	0.0167 (9)	0.0199 (9)	−0.0011 (7)	−0.0031 (7)	−0.0049 (7)
C20	0.0436 (12)	0.0252 (10)	0.0298 (10)	−0.0087 (9)	0.0092 (9)	−0.0109 (8)
C21	0.0521 (14)	0.0286 (11)	0.0304 (11)	−0.0050 (10)	0.0106 (10)	−0.0129 (9)
C22	0.0472 (12)	0.0226 (10)	0.0279 (10)	0.0007 (9)	−0.0066 (9)	−0.0125 (8)
C23	0.0417 (11)	0.0218 (10)	0.0322 (11)	−0.0062 (9)	−0.0093 (9)	−0.0096 (8)
C24	0.0344 (10)	0.0222 (9)	0.0230 (9)	−0.0064 (8)	−0.0041 (8)	−0.0065 (7)

Geometric parameters (Å, º) top

S1—C17	1.657 (2)	C3'—H3'2	0.9900
O1—C18	1.226 (2)	C4'—C5	1.532 (9)
N1—C10	1.320 (2)	C4'—H4'1	0.9900
N1—C7	1.354 (2)	C4'—H4'2	0.9900
N2—C14	1.366 (3)	C5—C6	1.513 (2)
N2—C11	1.382 (2)	C5—H5A	0.9900
N2—C15	1.452 (3)	C5—H5B	0.9900
N3—C16	1.147 (2)	C5—H5C	0.9900
N4—C17	1.344 (3)	C5—H5D	0.9900
N4—C10	1.416 (2)	C6—C7	1.398 (3)
N4—H4	0.8800	C6—C8	1.402 (3)
N5—C18	1.380 (2)	C8—C9	1.405 (2)
N5—C17	1.399 (2)	C8—C11	1.468 (2)
N5—H5	0.8800	C9—C10	1.395 (3)
C1—C2	1.521 (4)	C9—C16	1.440 (2)
C1—H1A	0.9800	C11—C12	1.379 (3)
C1—H1B	0.9800	C12—C13	1.412 (3)
C1—H1C	0.9800	C12—H12	0.9500
C2—C3	1.500 (5)	C13—C14	1.366 (3)
C2—C7	1.547 (3)	C13—H13	0.9500
C2—H2	1.0000	C14—H14	0.9500
C3—C4	1.511 (6)	C15—H15A	0.9800
C3—H3A	0.9900	C15—H15B	0.9800
C3—H3B	0.9900	C15—H15C	0.9800
C4—C5	1.527 (7)	C18—C19	1.497 (2)
C4—H4A	0.9900	C19—C24	1.386 (3)
C4—H4B	0.9900	C19—C20	1.391 (3)
C1'—C2'	1.510 (6)	C20—C21	1.393 (3)
C1'—H1'A	0.9800	C20—H20	0.9500
C1'—H1'B	0.9800	C21—C22	1.380 (4)
C1'—H1'C	0.9800	C21—H21	0.9500
C2'—C3'	1.513 (6)	C22—C23	1.385 (3)
C2'—C7	1.563 (5)	C22—H22	0.9500
C2'—H2'	1.0000	C23—C24	1.396 (3)
C3'—C4'	1.508 (9)	C23—H23	0.9500
C3'—H3'1	0.9900	C24—H24	0.9500

C10—N1—C7	118.70 (16)	C6—C5—H5C	109.8
C14—N2—C11	108.27 (16)	C4—C5—H5C	111.7
C14—N2—C15	123.49 (17)	C4'—C5—H5C	109.7
C11—N2—C15	127.26 (17)	C6—C5—H5D	110.1
C17—N4—C10	125.08 (16)	C4—C5—H5D	101.5
C17—N4—H4	117.5	C4'—C5—H5D	111.1
C10—N4—H4	117.5	H5C—C5—H5D	108.3
C18—N5—C17	127.16 (16)	C7—C6—C8	117.99 (17)
C18—N5—H5	116.4	C7—C6—C5	121.05 (17)
C17—N5—H5	116.4	C8—C6—C5	120.94 (16)
C2—C1—H1A	109.5	N1—C7—C6	122.96 (17)
C2—C1—H1B	109.5	N1—C7—C2	114.67 (19)
H1A—C1—H1B	109.5	C6—C7—C2	120.51 (19)
C2—C1—H1C	109.5	N1—C7—C2'	112.4 (2)
H1A—C1—H1C	109.5	C6—C7—C2'	123.2 (2)
H1B—C1—H1C	109.5	C6—C8—C9	118.42 (16)
C3—C2—C1	113.7 (3)	C6—C8—C11	121.25 (16)
C3—C2—C7	112.8 (3)	C9—C8—C11	120.33 (16)
C1—C2—C7	108.8 (3)	C10—C9—C8	118.92 (16)
C3—C2—H2	107.1	C10—C9—C16	120.70 (16)
C1—C2—H2	107.1	C8—C9—C16	120.18 (16)
C7—C2—H2	107.1	N1—C10—C9	122.84 (17)
C2—C3—C4	115.0 (5)	N1—C10—N4	115.13 (16)
C2—C3—H3A	108.5	C9—C10—N4	121.96 (16)
C4—C3—H3A	108.5	C12—C11—N2	107.94 (16)
C2—C3—H3B	108.5	C12—C11—C8	129.53 (17)
C4—C3—H3B	108.5	N2—C11—C8	122.51 (17)
H3A—C3—H3B	107.5	C11—C12—C13	107.41 (18)
C3—C4—C5	110.0 (5)	C11—C12—H12	126.3
C3—C4—H4A	109.7	C13—C12—H12	126.3
C5—C4—H4A	109.7	C14—C13—C12	107.14 (17)
C3—C4—H4B	109.7	C14—C13—H13	126.4
C5—C4—H4B	109.7	C12—C13—H13	126.4
H4A—C4—H4B	108.2	N2—C14—C13	109.21 (17)
C2'—C1'—H1'A	109.5	N2—C14—H14	125.4
C2'—C1'—H1'B	109.5	C13—C14—H14	125.4
H1'A—C1'—H1'B	109.5	N2—C15—H15A	109.5
C2'—C1'—H1'C	109.5	N2—C15—H15B	109.5
H1'A—C1'—H1'C	109.5	H15A—C15—H15B	109.5
H1'B—C1'—H1'C	109.5	N2—C15—H15C	109.5
C1'—C2'—C3'	114.5 (4)	H15A—C15—H15C	109.5
C1'—C2'—C7	106.8 (4)	H15B—C15—H15C	109.5
C3'—C2'—C7	109.8 (4)	N3—C16—C9	176.5 (2)
C1'—C2'—H2'	108.5	N4—C17—N5	114.65 (16)
C3'—C2'—H2'	108.5	N4—C17—S1	125.98 (14)
C7—C2'—H2'	108.5	N5—C17—S1	119.31 (14)
C4'—C3'—C2'	114.1 (8)	O1—C18—N5	122.12 (16)
C4'—C3'—H3'1	108.7	O1—C18—C19	120.29 (17)
C2'—C3'—H3'1	108.7	N5—C18—C19	117.55 (16)
C4'—C3'—H3'2	108.7	C24—C19—C20	119.68 (18)
C2'—C3'—H3'2	108.7	C24—C19—C18	124.42 (17)
H3'1—C3'—H3'2	107.6	C20—C19—C18	115.74 (18)
C3'—C4'—C5	110.5 (8)	C19—C20—C21	120.4 (2)
C3'—C4'—H4'1	109.6	C19—C20—H20	119.8
C5—C4'—H4'1	109.6	C21—C20—H20	119.8
C3'—C4'—H4'2	109.6	C22—C21—C20	119.8 (2)
C5—C4'—H4'2	109.6	C22—C21—H21	120.1
H4'1—C4'—H4'2	108.1	C20—C21—H21	120.1
C6—C5—C4	114.9 (4)	C21—C22—C23	120.07 (19)
C6—C5—C4'	107.8 (6)	C21—C22—H22	120.0
C4—C5—C4'	10.0 (5)	C23—C22—H22	120.0
C6—C5—H5A	108.5	C22—C23—C24	120.4 (2)
C4—C5—H5A	108.5	C22—C23—H23	119.8
C4'—C5—H5A	105.9	C24—C23—H23	119.8
C6—C5—H5B	108.5	C19—C24—C23	119.7 (2)
C4—C5—H5B	108.5	C19—C24—H24	120.2
C4'—C5—H5B	118.2	C23—C24—H24	120.2
H5A—C5—H5B	107.5

C1—C2—C3—C4	−169.1 (6)	C7—N1—C10—C9	−1.1 (3)
C7—C2—C3—C4	−44.7 (7)	C7—N1—C10—N4	−178.1 (2)
C2—C3—C4—C5	56.7 (12)	C8—C9—C10—N1	4.3 (3)
C1'—C2'—C3'—C4'	92.8 (9)	C16—C9—C10—N1	−170.5 (2)
C7—C2'—C3'—C4'	−27.3 (9)	C8—C9—C10—N4	−178.92 (18)
C2'—C3'—C4'—C5	64.7 (16)	C16—C9—C10—N4	6.2 (3)
C3—C4—C5—C6	−45.1 (12)	C17—N4—C10—N1	−117.5 (2)
C3—C4—C5—C4'	0 (8)	C17—N4—C10—C9	65.6 (3)
C3'—C4'—C5—C6	−57.1 (15)	C14—N2—C11—C12	1.0 (2)
C3'—C4'—C5—C4	166 (10)	C15—N2—C11—C12	169.90 (18)
C4—C5—C6—C7	25.2 (6)	C14—N2—C11—C8	179.69 (16)
C4'—C5—C6—C7	17.8 (8)	C15—N2—C11—C8	−11.5 (3)
C4—C5—C6—C8	−153.3 (6)	C6—C8—C11—C12	−56.1 (3)
C4'—C5—C6—C8	−160.7 (8)	C9—C8—C11—C12	123.0 (2)
C10—N1—C7—C6	−2.0 (4)	C6—C8—C11—N2	125.6 (2)
C10—N1—C7—C2	−166.5 (2)	C9—C8—C11—N2	−55.3 (3)
C10—N1—C7—C2'	164.6 (3)	N2—C11—C12—C13	0.0 (2)
C8—C6—C7—N1	1.6 (4)	C8—C11—C12—C13	−178.49 (18)
C5—C6—C7—N1	−176.9 (2)	C11—C12—C13—C14	−1.1 (2)
C8—C6—C7—C2	165.3 (2)	C11—N2—C14—C13	−1.8 (2)
C5—C6—C7—C2	−13.2 (4)	C15—N2—C14—C13	−171.12 (18)
C8—C6—C7—C2'	−163.5 (3)	C12—C13—C14—N2	1.7 (2)
C5—C6—C7—C2'	17.9 (4)	C10—C9—C16—N3	100 (3)
C3—C2—C7—N1	−172.9 (3)	C8—C9—C16—N3	−75 (3)
C1—C2—C7—N1	−45.7 (4)	C10—N4—C17—N5	171.52 (17)
C3—C2—C7—C6	22.2 (4)	C10—N4—C17—S1	−5.9 (3)
C1—C2—C7—C6	149.3 (3)	C18—N5—C17—N4	−10.1 (3)
C3—C2—C7—C2'	−81.8 (5)	C18—N5—C17—S1	167.55 (15)
C1—C2—C7—C2'	45.4 (5)	C17—N5—C18—O1	13.3 (3)
C1'—C2'—C7—N1	55.5 (4)	C17—N5—C18—C19	−164.14 (17)
C3'—C2'—C7—N1	−179.8 (4)	O1—C18—C19—C24	−172.29 (18)
C1'—C2'—C7—C6	−138.0 (4)	N5—C18—C19—C24	5.2 (3)
C3'—C2'—C7—C6	−13.2 (5)	O1—C18—C19—C20	3.2 (3)
C1'—C2'—C7—C2	−45.2 (5)	N5—C18—C19—C20	−179.29 (17)
C3'—C2'—C7—C2	79.6 (6)	C24—C19—C20—C21	0.4 (3)
C7—C6—C8—C9	1.6 (3)	C18—C19—C20—C21	−175.3 (2)
C5—C6—C8—C9	−179.84 (18)	C19—C20—C21—C22	−0.4 (4)
C7—C6—C8—C11	−179.3 (2)	C20—C21—C22—C23	0.1 (3)
C5—C6—C8—C11	−0.7 (3)	C21—C22—C23—C24	0.2 (3)
C6—C8—C9—C10	−4.4 (3)	C20—C19—C24—C23	−0.1 (3)
C11—C8—C9—C10	176.45 (18)	C18—C19—C24—C23	175.20 (18)
C6—C8—C9—C16	170.46 (18)	C22—C23—C24—C19	−0.2 (3)
C11—C8—C9—C16	−8.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.88	1.90	2.594 (2)	135
N5—H5···N3ⁱ	0.88	2.22	3.058 (2)	158

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₅OS
M_r	429.53
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.7072 (4), 10.4928 (5), 11.8828 (5)
α, β, γ (°)	82.245 (4), 84.263 (3), 63.671 (4)
V (Å³)	1073.76 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.55
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.654, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	7386, 4218, 3897
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.146, 1.03
No. of reflections	4218
No. of parameters	294
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.46

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.88	1.90	2.594 (2)	135
N5—H5···N3ⁱ	0.88	2.22	3.058 (2)	158

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Cocco, M. T., Congiu, C., Lilliu, V. & Onnis, V. (2005). Eur. J. Med. Chem. 40, 1365–1372. Web of Science CrossRef PubMed CAS Google Scholar
El-Hawash, S. A. M., Abdel-Wahab, A. E. & El-Demellawy, M. A. (2006). Arch. Pharm. Chem. Life Sci. 339, 437–447. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2430

doi:10.1107/S1600536811033046

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

1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetra­hydro­quinolin-2-yl]thio­urea

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]thiourea