4-Chloro-butyl 7-chloro-1-cyclo-propyl-4-(1,3-diethyl-4,6-dioxo-2-sulfanyl-idene-1,3-diazinan-5-yl-idene)-6-fluoro-1,4-di-hydro-quinoline-3-carboxyl-ate.

The title compound, C25H26Cl2FN3O4S, contains two bio-active moieties (thio-barbituric acid and fluoro-quinolone). In the crystal, mol-ecules 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-chloro-butyl 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 ▶); Shishkin et al. (1997 ▶).

Experimental

Crystal data

C25H26Cl2FN3O4S

M = 554.45

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.230

S = 1.02

4664 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.40 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016024/bh2478sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016024/bh2478Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H26Cl2FN3O4S	F(000) = 2304
Mr = 554.45	Dx = 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

Agilent Xcalibur Eos diffractometer	4664 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −28→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
Tmin = 0.606, Tmax = 1.000	l = −19→18
12511 measured reflections

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(Fo2) + (0.1011P)2 + 5.5588P] where P = (Fo2 + 2Fc2)/3
4664 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.40 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .