4-Chloro­butyl 7-chloro-1-cyclo­propyl-4-(1,3-diethyl-4,6-dioxo-2-sulfanyl­idene-1,3-diazinan-5-yl­idene)-6-fluoro-1,4-di­hydro­quinoline-3-carboxyl­ate

Sweidan, K.; Haddad, S.F.; AlDamen, M.A.; Al-Sheikhb, A.

doi:10.1107/S1600536813016024

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1191

doi:10.1107/S1600536813016024

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4-Chlorobutyl 7-chloro-1-cyclopropyl-4-(1,3-diethyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)-6-fluoro-1,4-dihydroquinoline-3-carboxylate

Kamal Sweidan,^a Salim F. Haddad,^a ^* Murad A. AlDamen ^a and Ahmed Al-Sheikhb ^b

^aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan, and ^bFaculty of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia
^*Correspondence e-mail: hadsal2003@yahoo.com

(Received 22 April 2013; accepted 8 June 2013; online 3 July 2013)

The title compound, C₂₅H₂₆Cl₂FN₃O₄S, contains two bio-active moieties (thiobarbituric acid and fluoroquinolone). In the crystal, molecules are linked via C—H⋯O and C—H⋯F hydrogen bonds, forming two-dimensional slab-like networks lying parallel to the bc plane. The benzene ring substituted by F and Cl atoms and the 4-chlorobutyl group seem to be partly disordered, however attempts to model the disorder were unsuccessful.

Related literature

For the biological activity of fluoroquinolone derivatives, see: Li et al. (2000 ); Baker et al. (2004 ); Mitscher (2005 ). For the crystal structures of some fluoroquinolone and 1,3-diethyl-2-thiobarbituric acid derivatives, see: Al-Qawasmeh (2012 ); Sweidan et al. (2012 $[Sweidan, K., AlDamen, M. A., Maichle-Mö\, C. & Mubarak, M. S. (2012). J. Chem. Crystallogr. 42, 427-431.]$ ); Shishkin et al. (1997 ).

Experimental

Crystal data

C₂₅H₂₆Cl₂FN₃O₄S
M_r = 554.45
Monoclinic, C 2/c
a = 24.3035 (15) Å
b = 13.8310 (8) Å
c = 16.4507 (16) Å
β = 107.345 (8)°
V = 5278.3 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.30 × 0.15 × 0.06 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.606, T_max = 1.000
12511 measured reflections
4664 independent reflections
2477 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.230
S = 1.02
4664 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O2ⁱ	0.98	2.32	3.014 (6)	127
C20—H20A⋯O3ⁱⁱ	0.97	2.56	3.233 (6)	126
C25—H25A⋯F1ⁱⁱⁱ	0.97	2.51	3.371 (10)	148
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2011); 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: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813016024/bh2478sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813016024/bh2478Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813016024/bh2478Isup3.cml

checkCIF report

Comment top

A vast number of fluoroquinolones (Baker et al., 2004) such as ciprofloxacin and moxifloxacin have therapeutic efficacy as anti-infective agents (Li et al., 2000; Mitscher, 2005). The prepared molecule contains two bio-active moieties (thiobarbituric acid and fluoroquinolone), which may have a high impact biological effect.

From the X-ray structural analysis, it is interesting to note that this structure presents some zwitterionic character, since the bond length for C3—C10 is 1.449 (5) Å, intermediate between carbon-carbon single bond and double bond, while bond angles around C10 are close to 120°: C13—C10—C11 = 119.8 (4), C11—C10—C3 = 120.5 (4), and C13—C10—C3 = 119.5 (4)°. The crystal structure reveals the negative charge to be localized at the thiobarbituric-acid ring, with a contribution of the enolate form [C10—C11 = 1.418 (6), C10—C13 = 1.406 (6), C11—O1 = 1.231 (5), C13—O2 = 1.229 (5) Å; see Sweidan et al., 2012]. The carbon-sulfur bond length is 1.665 (5) Å, which is close to that observed in a 2-thioxo-1,2,3,4-tetrahydropyrimidine derivative [1.673 (9) Å, Shishkin et al., 1997; see also Al-Qawasmeh, 2012].

The displacement parameters in the 4-chlorobutyl branch are rather high, indicating, together with residual electron density in the vicinity, some degree of disorder. For example, C22—C23 bond length, 1.402 (9) Å, is a bit short for a single C—C bond. After convergence, it seems that benzene ring substituted by F1 and Cl1 could also be partly disordered. However, attempts to model such disordered parts did not improve the picture.

Related literature top

For the biological activity of fluoroquinolone derivatives, see: Li et al. (2000); Baker et al. (2004); Mitscher (2005). For the crystal structures of some fluoroquinolone and 1,3-diethyl-2-thiobarbituric acid derivatives, see: Al-Qawasmeh (2012); Sweidan et al. (2012); Shishkin et al. (1997).

Experimental top

The title compound was prepared as followed: 8 ml of thionyl chloride was added to a solution containing 1.5 g (5.3 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid in 15 ml of dry THF. The resulting solution was refluxed for 6 h, then cooled, and evaporated under reduced pressure to remove the excess thionyl chloride. To the resulting residue, a solution of 1,3-diethyl-2-thiobarbituric acid (1.19 g, 6.0 mmol) and 1.5 ml (10.0 mmol) of dry triethylamine in 20 ml of dry THF were added, at room temperature. After stirring overnight, the resulting precipitate was filtered off, washed with H₂O/THF (1:2), and dried under reduced pressure. Yield: 1.5 g (51%). This solid was recrystallized from dichloromethane/diethylether, affording brownish crystals. A flat elongated crystal was mounted and data collected using five omega scans and a total of 277 frames with an exposure time of 76 s per frame.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP drawing showing the molecular conformation of the title compound. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen atoms are represented as small spheres of arbitrary radii.

4-Chlorobutyl 7-chloro-1-cyclopropyl-4-(1,3-diethyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)-6-fluoro-1,4-dihydroquinoline-3-carboxylate top

Crystal data top

C₂₅H₂₆Cl₂FN₃O₄S	F(000) = 2304
M_r = 554.45	D_x = 1.395 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 2598 reflections
a = 24.3035 (15) Å	θ = 2.9–29.0°
b = 13.8310 (8) Å	µ = 0.37 mm⁻¹
c = 16.4507 (16) Å	T = 293 K
β = 107.345 (8)°	Parallelpiped, orange
V = 5278.3 (7) Å³	0.30 × 0.15 × 0.06 mm
Z = 8

Data collection top

Agilent Xcalibur Eos diffractometer	4664 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2477 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.0534 pixels mm^-1	θ_max = 25.0°, θ_min = 2.9°
ω scans	h = −28→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.606, T_max = 1.000	l = −19→18
12511 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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1011P)² + 5.5588P] where P = (F_o² + 2F_c²)/3
4664 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³
0 constraints

Crystal data top

C₂₅H₂₆Cl₂FN₃O₄S	V = 5278.3 (7) Å³
M_r = 554.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.3035 (15) Å	µ = 0.37 mm⁻¹
b = 13.8310 (8) Å	T = 293 K
c = 16.4507 (16) Å	0.30 × 0.15 × 0.06 mm
β = 107.345 (8)°

Data collection top

Agilent Xcalibur Eos diffractometer	4664 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2477 reflections with I > 2σ(I)
T_min = 0.606, T_max = 1.000	R_int = 0.047
12511 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.02	Δρ_max = 0.58 e Å⁻³
4664 reflections	Δρ_min = −0.40 e Å⁻³
325 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.24101 (6)	0.17120 (14)	0.14821 (12)	0.0943 (6)
Cl1	−0.19348 (8)	0.14374 (13)	0.09519 (18)	0.1377 (10)
Cl2	0.08427 (9)	1.00624 (14)	0.18342 (15)	0.1267 (8)
F1	−0.07857 (15)	0.0682 (2)	0.1166 (3)	0.1128 (14)
O1	0.03572 (14)	0.2291 (3)	0.0014 (2)	0.0712 (11)
O2	0.12679 (13)	0.4217 (2)	0.2354 (2)	0.0586 (9)
O3	0.08993 (13)	0.5366 (2)	0.0784 (2)	0.0578 (9)
O4	0.06525 (13)	0.6089 (2)	0.1858 (2)	0.0612 (10)
N1	−0.08816 (13)	0.4624 (2)	0.1034 (2)	0.0369 (8)
N2	0.12960 (16)	0.2031 (3)	0.0780 (2)	0.0483 (10)
N3	0.17566 (15)	0.3066 (3)	0.1881 (2)	0.0531 (11)
C1	−0.08558 (17)	0.3631 (3)	0.1035 (3)	0.0405 (10)
C2	−0.03227 (17)	0.3163 (3)	0.1127 (3)	0.0390 (10)
C3	0.01920 (16)	0.3715 (3)	0.1196 (2)	0.0374 (10)
C4	0.01378 (17)	0.4713 (3)	0.1244 (3)	0.0377 (10)
C5	−0.03978 (18)	0.5125 (3)	0.1162 (3)	0.0401 (10)
H5A	−0.0418	0.5794	0.1200	0.048*
C6	−0.1360 (2)	0.3092 (3)	0.0963 (3)	0.0552 (13)
H6A	−0.1710	0.3405	0.0887	0.066*
C7	−0.1331 (2)	0.2110 (4)	0.1008 (4)	0.0736 (17)
C8	−0.0802 (2)	0.1650 (4)	0.1120 (4)	0.0724 (17)
C9	−0.0314 (2)	0.2151 (3)	0.1193 (3)	0.0582 (14)
H9A	0.0033	0.1821	0.1287	0.070*
C10	0.07331 (17)	0.3246 (3)	0.1239 (3)	0.0401 (10)
C11	0.07575 (18)	0.2519 (3)	0.0643 (3)	0.0462 (11)
C12	0.1791 (2)	0.2288 (4)	0.1375 (3)	0.0516 (12)
C13	0.12424 (17)	0.3552 (3)	0.1849 (3)	0.0434 (11)
C14	0.1290 (2)	0.1194 (4)	0.0207 (4)	0.0677 (15)
H14A	0.1561	0.0711	0.0517	0.081*
H14B	0.0909	0.0905	0.0041	0.081*
C15	0.1443 (3)	0.1470 (4)	−0.0569 (4)	0.092 (2)
H15A	0.1433	0.0907	−0.0915	0.138*
H15B	0.1823	0.1743	−0.0409	0.138*
H15C	0.1171	0.1938	−0.0886	0.138*
C16	0.2289 (2)	0.3434 (5)	0.2500 (4)	0.0736 (17)
H16A	0.2564	0.2910	0.2675	0.088*
H16B	0.2200	0.3671	0.3001	0.088*
C17	0.2549 (3)	0.4222 (6)	0.2130 (5)	0.107 (2)
H17A	0.2893	0.4446	0.2545	0.161*
H17B	0.2279	0.4746	0.1965	0.161*
H17C	0.2643	0.3985	0.1639	0.161*
C18	−0.14249 (17)	0.5130 (3)	0.0928 (3)	0.0437 (11)
H18A	−0.1549	0.5188	0.1441	0.052*
C19	−0.1571 (2)	0.5954 (4)	0.0329 (3)	0.0594 (14)
H19A	−0.1768	0.6502	0.0484	0.071*
H19B	−0.1302	0.6116	0.0016	0.071*
C20	−0.1889 (2)	0.5045 (4)	0.0120 (3)	0.0610 (14)
H20A	−0.1817	0.4647	−0.0324	0.073*
H20B	−0.2283	0.5032	0.0144	0.073*
C21	0.06135 (18)	0.5399 (3)	0.1271 (3)	0.0455 (11)
C22	0.1124 (3)	0.6771 (5)	0.1981 (5)	0.094 (2)
H22A	0.1302	0.6866	0.2587	0.113*
H22B	0.1412	0.6496	0.1749	0.113*
C23	0.0952 (3)	0.7671 (6)	0.1597 (6)	0.130 (3)
H23A	0.0825	0.7578	0.0985	0.156*
H23B	0.1288	0.8087	0.1728	0.156*
C24	0.0490 (3)	0.8188 (5)	0.1840 (6)	0.112 (2)
H24A	0.0610	0.8283	0.2452	0.134*
H24B	0.0146	0.7789	0.1694	0.134*
C25	0.0342 (4)	0.9178 (6)	0.1395 (6)	0.145 (4)
H25A	−0.0032	0.9385	0.1429	0.174*
H25B	0.0314	0.9106	0.0798	0.174*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0580 (9)	0.1077 (14)	0.1167 (15)	0.0380 (9)	0.0255 (9)	−0.0067 (10)
Cl1	0.0780 (11)	0.0645 (11)	0.284 (3)	−0.0280 (9)	0.0751 (15)	−0.0082 (14)
Cl2	0.1264 (17)	0.0849 (14)	0.161 (2)	−0.0058 (12)	0.0313 (15)	0.0051 (12)
F1	0.094 (3)	0.0357 (18)	0.222 (5)	−0.0059 (17)	0.067 (3)	0.003 (2)
O1	0.052 (2)	0.082 (3)	0.072 (3)	0.0024 (19)	0.0056 (19)	−0.036 (2)
O2	0.0491 (19)	0.075 (2)	0.043 (2)	0.0087 (17)	0.0004 (16)	−0.0185 (17)
O3	0.0477 (18)	0.070 (2)	0.060 (2)	−0.0072 (17)	0.0225 (17)	−0.0007 (17)
O4	0.0503 (19)	0.046 (2)	0.090 (3)	−0.0131 (16)	0.0254 (19)	−0.0231 (18)
N1	0.0313 (18)	0.036 (2)	0.045 (2)	0.0007 (16)	0.0143 (16)	−0.0002 (16)
N2	0.048 (2)	0.042 (2)	0.061 (3)	0.0062 (18)	0.027 (2)	−0.0024 (18)
N3	0.035 (2)	0.073 (3)	0.047 (2)	0.0094 (19)	0.0070 (18)	−0.008 (2)
C1	0.038 (2)	0.039 (3)	0.046 (3)	−0.003 (2)	0.017 (2)	−0.002 (2)
C2	0.038 (2)	0.037 (2)	0.043 (3)	0.003 (2)	0.012 (2)	−0.0028 (19)
C3	0.035 (2)	0.042 (3)	0.035 (2)	0.001 (2)	0.0089 (19)	−0.0015 (18)
C4	0.036 (2)	0.040 (3)	0.038 (3)	−0.001 (2)	0.0111 (19)	−0.0021 (18)
C5	0.043 (2)	0.037 (2)	0.042 (3)	−0.002 (2)	0.015 (2)	−0.0022 (19)
C6	0.042 (3)	0.046 (3)	0.080 (4)	−0.003 (2)	0.022 (3)	−0.003 (2)
C7	0.057 (3)	0.051 (3)	0.120 (5)	−0.016 (3)	0.036 (3)	−0.009 (3)
C8	0.065 (4)	0.036 (3)	0.126 (5)	0.000 (3)	0.044 (4)	0.000 (3)
C9	0.051 (3)	0.042 (3)	0.086 (4)	0.005 (2)	0.027 (3)	0.004 (2)
C10	0.038 (2)	0.041 (3)	0.041 (3)	0.003 (2)	0.012 (2)	−0.0051 (19)
C11	0.039 (2)	0.046 (3)	0.056 (3)	0.003 (2)	0.018 (2)	−0.005 (2)
C12	0.046 (3)	0.059 (3)	0.052 (3)	0.009 (2)	0.018 (2)	0.003 (2)
C13	0.037 (2)	0.056 (3)	0.037 (3)	0.005 (2)	0.011 (2)	−0.004 (2)
C14	0.069 (3)	0.049 (3)	0.092 (4)	−0.001 (3)	0.035 (3)	−0.021 (3)
C15	0.118 (5)	0.074 (4)	0.106 (5)	−0.016 (4)	0.066 (4)	−0.034 (4)
C16	0.044 (3)	0.108 (5)	0.057 (4)	0.010 (3)	−0.003 (3)	−0.010 (3)
C17	0.070 (4)	0.130 (6)	0.105 (6)	−0.020 (4)	0.001 (4)	−0.013 (5)
C18	0.035 (2)	0.050 (3)	0.049 (3)	0.008 (2)	0.017 (2)	0.006 (2)
C19	0.046 (3)	0.060 (3)	0.077 (4)	0.014 (3)	0.026 (3)	0.024 (3)
C20	0.038 (3)	0.073 (4)	0.071 (4)	0.010 (3)	0.014 (3)	0.005 (3)
C21	0.037 (2)	0.047 (3)	0.051 (3)	−0.001 (2)	0.011 (2)	0.000 (2)
C22	0.067 (4)	0.065 (4)	0.145 (7)	−0.019 (3)	0.023 (4)	−0.037 (4)
C23	0.068 (5)	0.105 (6)	0.203 (9)	−0.009 (5)	0.019 (5)	0.021 (6)
C24	0.088 (5)	0.091 (5)	0.150 (7)	−0.004 (4)	0.027 (5)	−0.002 (5)
C25	0.119 (7)	0.102 (6)	0.170 (9)	−0.009 (5)	−0.022 (6)	−0.002 (6)

Geometric parameters (Å, º) top

S1—C12	1.665 (5)	C10—C11	1.418 (6)
Cl1—C7	1.717 (5)	C14—C15	1.481 (8)
Cl2—C25	1.725 (7)	C14—H14A	0.9700
F1—C8	1.341 (6)	C14—H14B	0.9700
O1—C11	1.231 (5)	C15—H15A	0.9600
O2—C13	1.229 (5)	C15—H15B	0.9600
O3—C21	1.208 (5)	C15—H15C	0.9600
O4—C21	1.340 (5)	C16—C17	1.479 (8)
O4—C22	1.451 (6)	C16—H16A	0.9700
N1—C5	1.326 (5)	C16—H16B	0.9700
N1—C1	1.375 (5)	C17—H17A	0.9600
N1—C18	1.458 (5)	C17—H17B	0.9600
N2—C12	1.352 (6)	C17—H17C	0.9600
N2—C11	1.429 (5)	C18—C20	1.469 (6)
N2—C14	1.491 (6)	C18—C19	1.479 (6)
N3—C12	1.379 (6)	C18—H18A	0.9800
N3—C13	1.406 (5)	C19—C20	1.462 (7)
N3—C16	1.477 (6)	C19—H19A	0.9700
C1—C6	1.409 (6)	C19—H19B	0.9700
C1—C2	1.415 (5)	C20—H20A	0.9700
C2—C9	1.404 (6)	C20—H20B	0.9700
C2—C3	1.441 (5)	C22—C23	1.402 (9)
C3—C4	1.391 (6)	C22—H22A	0.9700
C3—C10	1.449 (5)	C22—H22B	0.9700
C4—C5	1.390 (5)	C23—C24	1.484 (10)
C4—C21	1.486 (6)	C23—H23A	0.9700
C5—H5A	0.9300	C23—H23B	0.9700
C6—C7	1.361 (7)	C24—C25	1.544 (10)
C6—H6A	0.9300	C24—H24A	0.9700
C7—C8	1.396 (7)	C24—H24B	0.9700
C8—C9	1.348 (7)	C25—H25A	0.9700
C9—H9A	0.9300	C25—H25B	0.9700
C10—C13	1.406 (6)

C21—O4—C22	116.5 (4)	H15A—C15—H15C	109.5
C5—N1—C1	118.9 (3)	H15B—C15—H15C	109.5
C5—N1—C18	119.8 (3)	N3—C16—C17	111.4 (5)
C1—N1—C18	121.3 (3)	N3—C16—H16A	109.4
C12—N2—C11	124.5 (4)	C17—C16—H16A	109.4
C12—N2—C14	120.0 (4)	N3—C16—H16B	109.4
C11—N2—C14	115.5 (4)	C17—C16—H16B	109.4
C12—N3—C13	124.3 (4)	H16A—C16—H16B	108.0
C12—N3—C16	119.1 (4)	C16—C17—H17A	109.5
C13—N3—C16	116.6 (4)	C16—C17—H17B	109.5
N1—C1—C6	119.4 (4)	H17A—C17—H17B	109.5
N1—C1—C2	119.8 (4)	C16—C17—H17C	109.5
C6—C1—C2	120.8 (4)	H17A—C17—H17C	109.5
C9—C2—C1	117.2 (4)	H17B—C17—H17C	109.5
C9—C2—C3	122.0 (4)	N1—C18—C20	119.5 (4)
C1—C2—C3	120.8 (4)	N1—C18—C19	118.6 (4)
C4—C3—C2	115.8 (3)	C20—C18—C19	59.5 (3)
C4—C3—C10	122.8 (4)	N1—C18—H18A	115.9
C2—C3—C10	121.3 (4)	C20—C18—H18A	115.9
C5—C4—C3	120.2 (4)	C19—C18—H18A	115.9
C5—C4—C21	116.0 (4)	C20—C19—C18	59.9 (3)
C3—C4—C21	123.3 (4)	C20—C19—H19A	117.8
N1—C5—C4	124.1 (4)	C18—C19—H19A	117.8
N1—C5—H5A	117.9	C20—C19—H19B	117.8
C4—C5—H5A	117.9	C18—C19—H19B	117.8
C7—C6—C1	119.6 (4)	H19A—C19—H19B	114.9
C7—C6—H6A	120.2	C19—C20—C18	60.6 (3)
C1—C6—H6A	120.2	C19—C20—H20A	117.7
C6—C7—C8	119.6 (5)	C18—C20—H20A	117.7
C6—C7—Cl1	120.5 (4)	C19—C20—H20B	117.7
C8—C7—Cl1	119.9 (4)	C18—C20—H20B	117.7
F1—C8—C9	119.8 (5)	H20A—C20—H20B	114.8
F1—C8—C7	118.3 (5)	O3—C21—O4	125.1 (4)
C9—C8—C7	121.9 (5)	O3—C21—C4	123.4 (4)
C8—C9—C2	120.9 (4)	O4—C21—C4	111.3 (4)
C8—C9—H9A	119.6	C23—C22—O4	113.5 (6)
C2—C9—H9A	119.6	C23—C22—H22A	108.9
C13—C10—C11	119.8 (4)	O4—C22—H22A	108.9
C13—C10—C3	119.5 (4)	C23—C22—H22B	108.9
C11—C10—C3	120.5 (4)	O4—C22—H22B	108.9
O1—C11—C10	125.3 (4)	H22A—C22—H22B	107.7
O1—C11—N2	118.0 (4)	C22—C23—C24	117.0 (8)
C10—C11—N2	116.8 (4)	C22—C23—H23A	108.1
N2—C12—N3	116.2 (4)	C24—C23—H23A	108.1
N2—C12—S1	122.2 (4)	C22—C23—H23B	108.1
N3—C12—S1	121.7 (4)	C24—C23—H23B	108.1
O2—C13—N3	117.9 (4)	H23A—C23—H23B	107.3
O2—C13—C10	124.4 (4)	C23—C24—C25	112.8 (7)
N3—C13—C10	117.8 (4)	C23—C24—H24A	109.0
C15—C14—N2	112.8 (4)	C25—C24—H24A	109.0
C15—C14—H14A	109.0	C23—C24—H24B	109.0
N2—C14—H14A	109.0	C25—C24—H24B	109.0
C15—C14—H14B	109.0	H24A—C24—H24B	107.8
N2—C14—H14B	109.0	C24—C25—Cl2	113.3 (6)
H14A—C14—H14B	107.8	C24—C25—H25A	108.9
C14—C15—H15A	109.5	Cl2—C25—H25A	108.9
C14—C15—H15B	109.5	C24—C25—H25B	108.9
H15A—C15—H15B	109.5	Cl2—C25—H25B	108.9
C14—C15—H15C	109.5	H25A—C25—H25B	107.7

C5—N1—C1—C6	175.2 (4)	C12—N2—C11—O1	171.1 (5)
C18—N1—C1—C6	−2.4 (6)	C14—N2—C11—O1	−8.3 (6)
C5—N1—C1—C2	−3.3 (6)	C12—N2—C11—C10	−7.7 (6)
C18—N1—C1—C2	179.1 (4)	C14—N2—C11—C10	173.0 (4)
N1—C1—C2—C9	175.0 (4)	C11—N2—C12—N3	1.1 (7)
C6—C1—C2—C9	−3.5 (6)	C14—N2—C12—N3	−179.6 (4)
N1—C1—C2—C3	−1.8 (6)	C11—N2—C12—S1	−177.9 (3)
C6—C1—C2—C3	179.7 (4)	C14—N2—C12—S1	1.4 (6)
C9—C2—C3—C4	−171.0 (4)	C13—N3—C12—N2	4.1 (7)
C1—C2—C3—C4	5.6 (6)	C16—N3—C12—N2	−175.3 (4)
C9—C2—C3—C10	7.2 (6)	C13—N3—C12—S1	−176.8 (4)
C1—C2—C3—C10	−176.3 (4)	C16—N3—C12—S1	3.7 (7)
C2—C3—C4—C5	−4.6 (6)	C12—N3—C13—O2	177.8 (4)
C10—C3—C4—C5	177.3 (4)	C16—N3—C13—O2	−2.7 (6)
C2—C3—C4—C21	−176.7 (4)	C12—N3—C13—C10	−2.3 (7)
C10—C3—C4—C21	5.2 (6)	C16—N3—C13—C10	177.1 (4)
C1—N1—C5—C4	4.5 (6)	C11—C10—C13—O2	175.2 (4)
C18—N1—C5—C4	−177.9 (4)	C3—C10—C13—O2	−1.3 (7)
C3—C4—C5—N1	−0.3 (6)	C11—C10—C13—N3	−4.7 (6)
C21—C4—C5—N1	172.3 (4)	C3—C10—C13—N3	178.8 (4)
N1—C1—C6—C7	−176.7 (5)	C12—N2—C14—C15	−87.5 (6)
C2—C1—C6—C7	1.8 (7)	C11—N2—C14—C15	91.9 (6)
C1—C6—C7—C8	−0.2 (9)	C12—N3—C16—C17	92.7 (6)
C1—C6—C7—Cl1	178.2 (4)	C13—N3—C16—C17	−86.8 (6)
C6—C7—C8—F1	179.6 (5)	C5—N1—C18—C20	117.2 (5)
Cl1—C7—C8—F1	1.2 (8)	C1—N1—C18—C20	−65.2 (5)
C6—C7—C8—C9	0.5 (10)	C5—N1—C18—C19	48.1 (6)
Cl1—C7—C8—C9	−178.0 (5)	C1—N1—C18—C19	−134.3 (5)
F1—C8—C9—C2	178.6 (5)	N1—C18—C19—C20	109.3 (5)
C7—C8—C9—C2	−2.3 (9)	N1—C18—C20—C19	−107.7 (4)
C1—C2—C9—C8	3.8 (7)	C22—O4—C21—O3	−8.1 (7)
C3—C2—C9—C8	−179.5 (5)	C22—O4—C21—C4	176.5 (4)
C4—C3—C10—C13	43.7 (6)	C5—C4—C21—O3	−123.8 (5)
C2—C3—C10—C13	−134.2 (4)	C3—C4—C21—O3	48.6 (7)
C4—C3—C10—C11	−132.7 (5)	C5—C4—C21—O4	51.7 (5)
C2—C3—C10—C11	49.3 (6)	C3—C4—C21—O4	−135.9 (4)
C13—C10—C11—O1	−169.4 (5)	C21—O4—C22—C23	102.8 (7)
C3—C10—C11—O1	7.0 (7)	O4—C22—C23—C24	55.7 (10)
C13—C10—C11—N2	9.3 (6)	C22—C23—C24—C25	178.9 (7)
C3—C10—C11—N2	−174.3 (4)	C23—C24—C25—Cl2	−76.6 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2ⁱ	0.98	2.32	3.014 (6)	127
C20—H20A···O3ⁱⁱ	0.97	2.56	3.233 (6)	126
C25—H25A···F1ⁱⁱⁱ	0.97	2.51	3.371 (10)	148

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆Cl₂FN₃O₄S
M_r	554.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.3035 (15), 13.8310 (8), 16.4507 (16)
β (°)	107.345 (8)
V (Å³)	5278.3 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.30 × 0.15 × 0.06

Data collection
Diffractometer	Agilent Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.606, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12511, 4664, 2477
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.230, 1.02
No. of reflections	4664
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.40

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2ⁱ	0.98	2.32	3.014 (6)	127
C20—H20A···O3ⁱⁱ	0.97	2.56	3.233 (6)	126
C25—H25A···F1ⁱⁱⁱ	0.97	2.51	3.371 (10)	148

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

Acknowledgements

The authors gratefully acknowledge financial support from the Deanship of Scientific Research at the University of Jordan. The X-ray structural work was done at the Hamdi Mango Center for Scientific Research of The University of Jordan, Amman 11942, Jordan.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Qawasmeh, R. A. (2012). Acta Cryst. E68, o2533. CSD CrossRef IUCr Journals Google Scholar
Baker, W. R., Cai, S. P., Dimitroff, M., Fang, L. M., Huh, K. K., Ryckman, D. R., Shang, X., Shawar, R. M. & Therrien, J. H. (2004). J. Med. Chem. 47, 4693–4709. Web of Science CrossRef PubMed CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Li, Q., Mitscher, L. A. & Shen, L. L. (2000). Med. Res. Rev. 20, 231–293. Web of Science CrossRef PubMed CAS Google Scholar
Mitscher, L. A. (2005). Chem. Rev. 105, 559–592. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shishkin, O. V., Solomovich, E. V., Vakula, V. M. & Yaremenko, F. G. (1997). Russ. Chem. Bull. 46, 1838–1843. Web of Science CrossRef CAS Google Scholar
Sweidan, K., AlDamen, M. A., Maichle-Mö\, C. & Mubarak, M. S. (2012). J. Chem. Crystallogr. 42, 427–431. Google Scholar

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

4-Chloro­butyl 7-chloro-1-cyclo­propyl-4-(1,3-di­ethyl-4,6-dioxo-2-sulfanyl­­idene-1,3-diazinan-5-yl­­idene)-6-fluoro-1,4-di­hydro­quinoline-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Chlorobutyl 7-chloro-1-cyclopropyl-4-(1,3-diethyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)-6-fluoro-1,4-dihydroquinoline-3-carboxylate