5-Chloro-N-{4-oxo-2-[4-(trifluoro-meth-yl)phen-yl]-1,3-thia-zolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide.

In the title compound, C(25)H(17)ClF(3)N(3)O(2)S, the five-membered 1,3-thia-zolidine ring adopts a twist conformation. The three F atoms of the CF(3) group are disordered over two sets of sites with refined occupancies of 0.542 (18) and 0.458 (18). In the nine-membered 1H-indoline ring system, the 1H-pyrrole ring forms a dihedral angle of 4.7 (2)° with the benzene ring, while it is twisted at an angle of 46.5 (2)° with respect to the attached phenyl ring. The dihedral angle between the phenyl and trifluoro-methyl-substituted benzene rings is 56.0 (2)°. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules into a three-dimensional network. In addition, weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are observed.

Related literature

For medicinal applications of indole derivatives, see: Beale (2011 ▶); Brancale & Silvestri (2007 ▶); Cihan-Ustundag & Capan (2012 ▶); Oudard et al. (2011 ▶); Verma & Saraf (2008 ▶). For the definition of ring-puckering parameters, see: Cremer & Pople (1975 ▶). For related structures, see: Akkurt et al. (2010 ▶, 2011a ▶,b ▶,c ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H17ClF3N3O2S

M = 515.94

Tetragonal,

a = 22.9020 (6) Å

c = 18.3260 (6) Å

V = 9612.0 (6) Å3

Z = 16

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.57 × 0.43 × 0.29 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.849, T max = 0.919

71781 measured reflections

4968 independent reflections

3054 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.210

S = 1.05

4968 reflections

345 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.30 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039347/lh5532sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039347/lh5532Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039347/lh5532Isup3.cml

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

C25H17ClF3N3O2S	Dx = 1.426 Mg m−3
Mr = 515.94	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 45035 reflections
Hall symbol: -I 4ad	θ = 1.4–27.8°
a = 22.9020 (6) Å	µ = 0.30 mm−1
c = 18.3260 (6) Å	T = 296 K
V = 9612.0 (6) Å3	Prism, orange
Z = 16	0.57 × 0.43 × 0.29 mm
F(000) = 4224

Stoe IPDS 2 diffractometer	4968 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3054 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.076
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.8°
ω scans	h = −28→28
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −28→28
Tmin = 0.849, Tmax = 0.919	l = −22→22
71781 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1132P)2] where P = (Fo2 + 2Fc2)/3
4968 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.53 e Å−3
14 restraints	Δρmin = −0.30 e Å−3

Experimental. 1H-NMR (400 MHz) (DMSO d6/TMS) δ 3.80 (1H, d, J = 15.90 Hz, H5-thia.), 3.96 (1H, dd, J1 = 15.87 Hz, J2 = 1.71 Hz, H5-thia.), 5.97 (1H, s, H2-thia.), 7.19–7.21 (3H, m, 3-C6H5-ind.), 7.25–7.29 (3H, m, H6-ind, 3-C6H5-ind.) 7.43–7.51 (2H,m H4-, H7-ind.), 7.67 (2H, d, J = 8.23 Hz, 2-C6H4-(H2,6)-thia), 7.75 (2H, d, J = 8.31 Hz, 2-C6H4-(H3,5)-thia.), 10.19 (1H, s, CONH), 12.04 (1H, s, NH) p.p.m.; 13C-NMR (HMBC) (125 MHz) (DMSO-d6) δ 29.91 (C5-thia.), 61.66 (C2-thia.), 114.92 (C7-ind.), 119.24 (C3-ind.), 119.68 (C4-ind.) 125.13 (C6-ind.), 125.84 (C3a-ind), 126.25 (2-C6H4-(C3,5)-thia.), 127.18 (C5-ind.), 127.93 (C2-ind.), 128.92 (2-C6H4-(C2,6)-thia.), 133.06 (3-C6H5-(C1)-ind), 134.99 (C7a-ind), 144.17 (2-C6-H4-(C1)-thia.), 161.21 (CONH), 169.66 (C═O) p.p.m.; APCI+ m/z (%) = 516.1/518.2 (MH+, 29.4/12.7), 79.5 (100).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.52469 (9)	0.62509 (8)	0.11058 (7)	0.1214 (8)
S1	0.33741 (6)	0.62264 (6)	0.73456 (6)	0.0809 (5)
O1	0.44994 (13)	0.54850 (11)	0.54646 (14)	0.0633 (10)
O2	0.49070 (12)	0.64975 (16)	0.66104 (17)	0.0816 (13)
N1	0.50355 (13)	0.56361 (13)	0.41587 (15)	0.0493 (9)
N2	0.41564 (12)	0.64048 (12)	0.54712 (15)	0.0455 (9)
N3	0.39991 (12)	0.63564 (12)	0.61935 (14)	0.0439 (9)
C1	0.48360 (15)	0.62222 (16)	0.32162 (18)	0.0495 (11)
C2	0.48633 (19)	0.63894 (18)	0.2484 (2)	0.0623 (14)
C3	0.5236 (2)	0.6087 (2)	0.2038 (2)	0.0733 (16)
C4	0.5597 (2)	0.5641 (2)	0.2289 (2)	0.0763 (19)
C5	0.55736 (18)	0.5467 (2)	0.2994 (2)	0.0647 (14)
C6	0.51797 (15)	0.57519 (16)	0.34551 (18)	0.0481 (11)
C7	0.46139 (15)	0.60221 (14)	0.43855 (17)	0.0439 (11)
C8	0.44742 (15)	0.63943 (15)	0.38228 (18)	0.0464 (11)
C9	0.39990 (17)	0.68331 (16)	0.37637 (18)	0.0512 (11)
C10	0.34426 (19)	0.6712 (2)	0.3996 (2)	0.0657 (16)
C11	0.2991 (2)	0.7108 (3)	0.3882 (3)	0.0867 (19)
C12	0.3093 (3)	0.7615 (3)	0.3509 (3)	0.092 (2)
C13	0.3642 (3)	0.7747 (2)	0.3279 (2)	0.087 (2)
C14	0.4097 (2)	0.73647 (18)	0.3411 (2)	0.0683 (14)
C15	0.44188 (15)	0.59419 (14)	0.51464 (18)	0.0446 (11)
C16	0.43981 (16)	0.64471 (17)	0.6722 (2)	0.0523 (12)
C17	0.41203 (19)	0.6458 (2)	0.7458 (2)	0.0737 (16)
C18	0.33692 (18)	0.64343 (19)	0.6371 (2)	0.0647 (14)
C19	0.29649 (17)	0.60608 (18)	0.5938 (2)	0.0587 (14)
C20	0.3035 (2)	0.54741 (18)	0.5819 (3)	0.0733 (17)
C21	0.2629 (2)	0.5169 (2)	0.5429 (3)	0.0863 (19)
C22	0.21510 (19)	0.5420 (2)	0.5160 (3)	0.0747 (17)
C23	0.2074 (2)	0.5992 (3)	0.5246 (3)	0.092 (2)
C24	0.2472 (2)	0.6329 (2)	0.5623 (3)	0.0813 (18)
C25	0.1692 (3)	0.5063 (3)	0.4760 (4)	0.111 (3)	0.500
C25'	0.1692 (3)	0.5063 (3)	0.4760 (4)	0.111 (3)	0.500
F1	0.1487 (8)	0.5287 (4)	0.4197 (9)	0.197 (8)	0.542 (18)
F2	0.1278 (6)	0.4936 (8)	0.5184 (9)	0.252 (12)	0.542 (18)
F3	0.1890 (4)	0.4577 (4)	0.4534 (5)	0.108 (4)	0.542 (18)
F1'	0.1752 (7)	0.5149 (15)	0.4092 (6)	0.37 (2)	0.458 (18)
F2'	0.1190 (6)	0.5316 (11)	0.4860 (11)	0.227 (12)	0.458 (18)
F3'	0.1645 (14)	0.4561 (7)	0.494 (2)	0.42 (2)	0.458 (18)
H1	0.51850	0.53630	0.44220	0.0590*
H2	0.46370	0.66950	0.23060	0.0750*
H2A	0.40900	0.67210	0.52320	0.0550*
H4	0.58570	0.54610	0.19690	0.0920*
H5	0.58120	0.51680	0.31660	0.0780*
H10	0.33660	0.63610	0.42340	0.0790*
H11	0.26190	0.70280	0.40590	0.1040*
H12	0.27870	0.78700	0.34120	0.1100*
H13	0.37110	0.80950	0.30330	0.1040*
H14	0.44730	0.74630	0.32620	0.0820*
H17A	0.41340	0.68490	0.76600	0.0880*
H17B	0.43240	0.61960	0.77870	0.0880*
H18	0.32600	0.68460	0.63200	0.0770*
H20	0.33610	0.52830	0.60040	0.0880*
H21	0.26890	0.47720	0.53490	0.1030*
H23	0.17450	0.61690	0.50470	0.1100*
H24	0.24160	0.67300	0.56690	0.0970*

	U11	U22	U33	U12	U13	U23
Cl1	0.1764 (17)	0.1380 (14)	0.0499 (6)	0.0150 (11)	0.0362 (8)	0.0157 (7)
S1	0.0795 (8)	0.1053 (10)	0.0579 (6)	−0.0299 (7)	0.0263 (5)	−0.0225 (6)
O1	0.091 (2)	0.0421 (14)	0.0567 (15)	0.0209 (13)	0.0195 (14)	0.0083 (12)
O2	0.0434 (17)	0.129 (3)	0.0724 (19)	0.0023 (17)	−0.0013 (14)	−0.0113 (18)
N1	0.0518 (17)	0.0503 (17)	0.0459 (15)	0.0110 (14)	0.0002 (13)	−0.0016 (13)
N2	0.0564 (17)	0.0372 (15)	0.0430 (14)	0.0060 (13)	0.0052 (13)	0.0036 (12)
N3	0.0420 (16)	0.0464 (16)	0.0434 (15)	0.0043 (12)	0.0070 (12)	−0.0025 (12)
C1	0.047 (2)	0.057 (2)	0.0446 (18)	−0.0042 (17)	0.0022 (15)	0.0004 (16)
C2	0.075 (3)	0.062 (2)	0.050 (2)	−0.001 (2)	0.0029 (19)	0.0076 (18)
C3	0.090 (3)	0.088 (3)	0.042 (2)	−0.008 (3)	0.017 (2)	0.004 (2)
C4	0.072 (3)	0.097 (4)	0.060 (3)	0.006 (3)	0.021 (2)	−0.011 (2)
C5	0.059 (2)	0.078 (3)	0.057 (2)	0.013 (2)	0.0061 (19)	−0.007 (2)
C6	0.0431 (19)	0.059 (2)	0.0422 (17)	0.0002 (16)	0.0001 (14)	−0.0034 (16)
C7	0.049 (2)	0.0433 (18)	0.0395 (17)	0.0042 (15)	0.0011 (14)	−0.0007 (14)
C8	0.049 (2)	0.048 (2)	0.0423 (17)	0.0019 (16)	−0.0036 (15)	0.0008 (15)
C9	0.060 (2)	0.055 (2)	0.0385 (17)	0.0102 (18)	−0.0020 (16)	0.0012 (16)
C10	0.068 (3)	0.072 (3)	0.057 (2)	0.014 (2)	−0.007 (2)	0.007 (2)
C11	0.072 (3)	0.110 (4)	0.078 (3)	0.034 (3)	−0.007 (2)	0.009 (3)
C12	0.110 (4)	0.097 (4)	0.068 (3)	0.057 (3)	−0.018 (3)	0.005 (3)
C13	0.138 (5)	0.062 (3)	0.061 (3)	0.038 (3)	0.000 (3)	0.014 (2)
C14	0.090 (3)	0.059 (2)	0.056 (2)	0.017 (2)	0.008 (2)	0.0124 (19)
C15	0.0468 (19)	0.0401 (19)	0.0469 (18)	0.0047 (15)	0.0000 (15)	0.0019 (15)
C16	0.045 (2)	0.060 (2)	0.052 (2)	0.0065 (17)	0.0041 (17)	−0.0046 (17)
C17	0.074 (3)	0.094 (3)	0.053 (2)	−0.003 (2)	0.006 (2)	−0.013 (2)
C18	0.056 (2)	0.059 (2)	0.079 (3)	−0.0005 (19)	0.010 (2)	−0.011 (2)
C19	0.053 (2)	0.064 (3)	0.059 (2)	−0.016 (2)	0.0066 (18)	−0.0145 (18)
C20	0.062 (3)	0.056 (3)	0.102 (3)	0.012 (2)	−0.022 (2)	−0.004 (2)
C21	0.071 (3)	0.062 (3)	0.126 (4)	0.003 (2)	−0.016 (3)	−0.032 (3)
C22	0.058 (3)	0.083 (3)	0.083 (3)	0.009 (2)	−0.009 (2)	−0.023 (2)
C23	0.061 (3)	0.094 (4)	0.120 (4)	0.015 (3)	−0.034 (3)	−0.004 (3)
C24	0.071 (3)	0.052 (2)	0.121 (4)	0.017 (2)	0.006 (3)	−0.007 (3)
C25	0.085 (4)	0.106 (5)	0.141 (6)	0.004 (4)	−0.020 (4)	−0.041 (5)
C25'	0.085 (4)	0.106 (5)	0.141 (6)	0.004 (4)	−0.020 (4)	−0.041 (5)
F1	0.231 (16)	0.109 (7)	0.252 (17)	0.000 (6)	−0.205 (15)	−0.005 (7)
F2	0.110 (9)	0.37 (3)	0.275 (18)	−0.148 (12)	0.098 (11)	−0.244 (19)
F3	0.098 (5)	0.106 (7)	0.120 (7)	−0.009 (4)	−0.037 (5)	−0.063 (5)
F1'	0.112 (11)	0.88 (7)	0.105 (11)	−0.010 (19)	−0.014 (8)	−0.20 (2)
F2'	0.070 (7)	0.40 (3)	0.210 (18)	0.013 (12)	−0.056 (10)	−0.102 (18)
F3'	0.54 (5)	0.151 (18)	0.57 (5)	−0.16 (2)	−0.42 (4)	0.14 (3)

Cl1—C3	1.749 (4)	C12—C13	1.360 (9)
S1—C17	1.801 (5)	C13—C14	1.382 (7)
S1—C18	1.849 (4)	C16—C17	1.492 (5)
O1—C15	1.212 (4)	C18—C19	1.490 (6)
O2—C16	1.189 (5)	C19—C20	1.371 (6)
N1—C6	1.357 (4)	C19—C24	1.409 (6)
N1—C7	1.374 (4)	C20—C21	1.365 (7)
N2—N3	1.376 (4)	C21—C22	1.331 (7)
N2—C15	1.356 (4)	C22—C23	1.331 (8)
N3—C16	1.348 (5)	C22—C25	1.520 (8)
N3—C18	1.490 (5)	C22—C25'	1.520 (8)
N1—H1	0.8600	C23—C24	1.380 (7)
N2—H2A	0.8600	C2—H2	0.9300
C1—C2	1.397 (5)	C4—H4	0.9300
C1—C6	1.404 (5)	C5—H5	0.9300
C1—C8	1.441 (5)	C10—H10	0.9300
C2—C3	1.370 (6)	C11—H11	0.9300
C3—C4	1.392 (6)	C12—H12	0.9300
C4—C5	1.353 (5)	C13—H13	0.9300
C5—C6	1.398 (5)	C14—H14	0.9300
C7—C8	1.376 (5)	C17—H17A	0.9700
C7—C15	1.476 (5)	C17—H17B	0.9700
C8—C9	1.485 (5)	C18—H18	0.9800
C9—C10	1.372 (6)	C20—H20	0.9300
C9—C14	1.397 (5)	C21—H21	0.9300
C10—C11	1.391 (7)	C23—H23	0.9300
C11—C12	1.368 (9)	C24—H24	0.9300
C17—S1—C18	92.32 (18)	S1—C18—C19	111.8 (3)
C6—N1—C7	109.4 (3)	C18—C19—C24	117.8 (4)
N3—N2—C15	118.4 (3)	C20—C19—C24	117.1 (4)
N2—N3—C16	120.1 (3)	C18—C19—C20	125.1 (4)
N2—N3—C18	117.0 (3)	C19—C20—C21	120.4 (4)
C16—N3—C18	118.8 (3)	C20—C21—C22	122.2 (4)
C7—N1—H1	125.00	C23—C22—C25'	119.7 (5)
C6—N1—H1	125.00	C21—C22—C25	121.0 (5)
N3—N2—H2A	121.00	C21—C22—C25'	121.0 (5)
C15—N2—H2A	121.00	C21—C22—C23	119.4 (5)
C2—C1—C6	119.0 (3)	C23—C22—C25	119.7 (5)
C2—C1—C8	133.8 (3)	C22—C23—C24	121.5 (5)
C6—C1—C8	107.0 (3)	C19—C24—C23	119.4 (4)
C1—C2—C3	117.6 (4)	C1—C2—H2	121.00
C2—C3—C4	122.9 (4)	C3—C2—H2	121.00
Cl1—C3—C2	118.9 (3)	C3—C4—H4	120.00
Cl1—C3—C4	118.1 (3)	C5—C4—H4	120.00
C3—C4—C5	120.5 (4)	C4—C5—H5	121.00
C4—C5—C6	117.7 (4)	C6—C5—H5	121.00
N1—C6—C1	108.0 (3)	C9—C10—H10	120.00
N1—C6—C5	129.8 (3)	C11—C10—H10	120.00
C1—C6—C5	122.1 (3)	C10—C11—H11	120.00
N1—C7—C8	109.6 (3)	C12—C11—H11	120.00
C8—C7—C15	135.7 (3)	C11—C12—H12	120.00
N1—C7—C15	114.8 (3)	C13—C12—H12	120.00
C1—C8—C7	106.0 (3)	C12—C13—H13	120.00
C1—C8—C9	123.4 (3)	C14—C13—H13	120.00
C7—C8—C9	130.1 (3)	C9—C14—H14	120.00
C10—C9—C14	118.0 (4)	C13—C14—H14	120.00
C8—C9—C14	120.4 (3)	S1—C17—H17A	110.00
C8—C9—C10	121.4 (3)	S1—C17—H17B	110.00
C9—C10—C11	120.8 (4)	C16—C17—H17A	110.00
C10—C11—C12	120.1 (5)	C16—C17—H17B	110.00
C11—C12—C13	120.1 (6)	H17A—C17—H17B	109.00
C12—C13—C14	120.1 (5)	S1—C18—H18	110.00
C9—C14—C13	120.8 (4)	N3—C18—H18	110.00
O1—C15—N2	122.1 (3)	C19—C18—H18	110.00
O1—C15—C7	121.1 (3)	C19—C20—H20	120.00
N2—C15—C7	116.9 (3)	C21—C20—H20	120.00
O2—C16—C17	124.9 (4)	C20—C21—H21	119.00
N3—C16—C17	111.3 (3)	C22—C21—H21	119.00
O2—C16—N3	123.8 (3)	C22—C23—H23	119.00
S1—C17—C16	107.2 (3)	C24—C23—H23	119.00
N3—C18—C19	114.6 (3)	C19—C24—H24	120.00
S1—C18—N3	100.0 (2)	C23—C24—H24	120.00
C17—S1—C18—C19	150.1 (3)	C15—C7—C8—C1	−179.5 (4)
C18—S1—C17—C16	−22.9 (3)	C15—C7—C8—C9	−8.0 (7)
C17—S1—C18—N3	28.4 (3)	N1—C7—C8—C1	−0.1 (4)
C6—N1—C7—C15	−180.0 (3)	N1—C7—C8—C9	171.4 (3)
C7—N1—C6—C1	−0.8 (4)	C8—C7—C15—O1	159.8 (4)
C6—N1—C7—C8	0.5 (4)	C8—C7—C15—N2	−21.3 (6)
C7—N1—C6—C5	−178.2 (4)	N1—C7—C15—N2	159.4 (3)
N3—N2—C15—O1	2.6 (5)	C7—C8—C9—C14	142.6 (4)
C15—N2—N3—C16	82.3 (4)	C7—C8—C9—C10	−43.0 (6)
C15—N2—N3—C18	−120.9 (3)	C1—C8—C9—C10	127.2 (4)
N3—N2—C15—C7	−176.4 (3)	C1—C8—C9—C14	−47.2 (5)
C18—N3—C16—C17	15.4 (5)	C8—C9—C10—C11	−174.6 (4)
N2—N3—C18—C19	52.5 (4)	C8—C9—C14—C13	172.5 (3)
N2—N3—C16—C17	171.8 (3)	C10—C9—C14—C13	−2.2 (5)
C16—N3—C18—C19	−150.3 (3)	C14—C9—C10—C11	0.0 (6)
C16—N3—C18—S1	−30.6 (4)	C9—C10—C11—C12	2.6 (7)
C18—N3—C16—O2	−166.3 (4)	C10—C11—C12—C13	−3.2 (8)
N2—N3—C18—S1	172.2 (2)	C11—C12—C13—C14	1.1 (8)
N2—N3—C16—O2	−9.8 (6)	C12—C13—C14—C9	1.7 (6)
C8—C1—C2—C3	−173.9 (4)	O2—C16—C17—S1	−169.2 (4)
C6—C1—C2—C3	−1.1 (6)	N3—C16—C17—S1	9.1 (4)
C6—C1—C8—C7	−0.4 (4)	S1—C18—C19—C20	−65.7 (5)
C2—C1—C6—N1	−173.9 (3)	S1—C18—C19—C24	114.5 (4)
C2—C1—C6—C5	3.8 (6)	N3—C18—C19—C20	47.2 (5)
C2—C1—C8—C9	0.9 (6)	N3—C18—C19—C24	−132.6 (4)
C2—C1—C8—C7	173.1 (4)	C18—C19—C20—C21	178.2 (4)
C6—C1—C8—C9	−172.6 (3)	C24—C19—C20—C21	−2.0 (7)
C8—C1—C6—C5	178.4 (3)	C18—C19—C24—C23	−177.1 (4)
C8—C1—C6—N1	0.7 (4)	C20—C19—C24—C23	3.1 (7)
C1—C2—C3—Cl1	175.8 (3)	C19—C20—C21—C22	−1.0 (8)
C1—C2—C3—C4	−2.3 (7)	C20—C21—C22—C23	2.8 (8)
Cl1—C3—C4—C5	−175.0 (4)	C20—C21—C22—C25	−177.0 (5)
C2—C3—C4—C5	3.1 (7)	C20—C21—C22—C25'	−177.0 (5)
C3—C4—C5—C6	−0.4 (6)	C21—C22—C23—C24	−1.6 (8)
C4—C5—C6—N1	174.1 (4)	C25—C22—C23—C24	178.2 (5)
C4—C5—C6—C1	−3.0 (6)	C25'—C22—C23—C24	178.2 (5)
N1—C7—C15—O1	−19.5 (5)	C22—C23—C24—C19	−1.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.08	2.864 (4)	151
N2—H2A···O2ii	0.86	2.34	2.851 (4)	118
C18—H18···O2ii	0.98	2.53	3.145 (5)	121
C21—H21···F3	0.93	2.40	2.719 (10)	100
C24—H24···Cg1iii	0.93	2.77	3.438 (5)	129
C17—H17B···Cg2iv	0.97	2.95	3.799 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.08	2.864 (4)	151
N2—H2A⋯O2ii	0.86	2.34	2.851 (4)	118
C18—H18⋯O2ii	0.98	2.53	3.145 (5)	121
C24—H24⋯Cg1iii	0.93	2.77	3.438 (5)	129
C17—H17B⋯Cg2iv	0.97	2.95	3.799 (5)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .