8,8′-Di­chloro-1,1′,5,5′-tetra­hydro-10,10′-bipyrrolo­[1,2-b]­iso­quinoline-3,3′(2H,2′H)-dione

Camus, F.; Norberg, B.; Bourry, A.; Akué-Gédu, R.; Rigo, B.; Durant, F.

doi:10.1107/S1600536803013436

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8,8′-Dichloro-1,1′,5,5′-tetrahydro-10,10′-bipyrrolo[1,2-b]isoquinoline-3,3′(2H,2′H)-dione

F. Camus, B. Norberg, A. Bourry, R. Akué-Gédu, B. Rigo and F. Durant

In the course of a study of keto lactams, treatment of 8-chloro-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione with concentrated hydrochloric acid was realised. The packing of the resultant dimeric compound, C₂₄H₁₈N₂O₂Cl₂, is governed by the formation of π-stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013436/dn6081sup1.cif Contains datablocks global, VI
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013436/dn6081VIsup2.hkl Contains datablock VI

CCDC reference: 217473

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.135
Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Cyclized keto lactams of general structure (I) (Rigo et al., 1990) proved to be of great interest due to the large diversity of rearrangements observed in this family of compounds (Rigo et al., 1991, 1994). Particularly, treatment of ketone (I) with polyphosphoric acid led to a dehydration, yielding lactam (II). During attempts to repeat this reaction with ketone (III) and concentrated hydrochloric acid, acid (IV) (19%), acid (V) (31%), dimer (VI) (25%) and diethylenic lactam (VII) (3%) were obtained. NMR spectral measurements easily lead to the structure of (IV), (V), and (VII), and show that compound (VI) seems to be a dimer of the known (Rigo & Kolocouris, 1983) general structure (VIII). The spatial structure of (VI) was confirmed as 8,8'-dichloro-1,1',5,5'-tetrahydro-10,10'-bipyrrolo[1,2-b]isoquinoline- 3,3'(2H,2'H)-dione, (VI), by an X-ray analysis of the yellow crystals obtained by slow evaporation of a DMF/benzene solution at room temperature.

Compound (VI) is composed of two perpendicular tricyclic entities [torsion angle C12—C11—C31—C30 = 95.5 (3)°] (Fig. 1). We note the coplanarity of each tricyclic part of the molecule. The sp² hybridization of atoms N6 and N26 is confirmed [the sums of the bond angles around N6 and N26 are 359.2 (2) and 359.4 (2)°, respectively]. Moreover, the crystal packing is governed by the formation of stacked π–π interactions between the aromatic rings (C1–C4/C12/C13) of two neighbouring molecules in the unit cell [(i) and (ii)] (Fig. 2). The distance between the two corresponding centroids is 3.89 (1) Å. A similar interaction exists between two other aromatic rings of two other neighbouring molecules [(i) and (iii)] (Fig. 2). In this case, the distance between the two corresponding centroids is 4.04 (1) Å. We found no classical hydrogen bonds.

Experimental top

A stirred mixture solution of ketone (III) (1.0 g, mmol) in concentrated hydrochloric acid (10 ml) was refluxed for 36 h. After cooling, the yellow crystals were filtered off, giving (VI), 19%, m.p. > 493 K (DMF/benzene). ¹H NMR (δ p.p.m.): 2.59 (s, 8H), 4.92 (d, J = 16.9 Hz, 2H), 5.04 (d, J = 16.9 Hz, 2H), 6.80 (d, J = 1.9 Hz, 2H), 7.04 (d, J = 8.2 Hz, 2H), 7.11 (dd, J = 8.2, 1.9 Hz, 2H); ¹³C NMR (δ p.p.m.): 22.5, 28.4, 43.3, 102.4, 121.9, 125.0, 126.4, 127.7, 133.3, 134.0, 141.8, 175.0. The water solution was extracted with dichloromethane, giving lactam (VI), 3%, m.p. 481–482 K (CH₂Cl₂). ¹H NMR (δ p.p.m): 4.93 (s, 2H), 6.15 (s, 1H), 6.35 (d, J = 5.6 Hz, 1H), 7.16 (d, J = 8.9 Hz, 1H), 7.17 (d, J = 5.6 Hz, 1H), 7.23 (s, 1H), 7.26 (d, J = 8.6 Hz, 1H); ¹³C NMR (δ p.p.m.): 42.2, 108.8, 125.0, 127.6, 128.0, 128.4, 128.7, 131.6, 133.3, 133.4, 138.4, 169.1. The water solution was evaporated in part, giving acid (V), 31%, m.p. 208–210 K (H₂O). ¹H NMR (D₂O/NaOD): δ 2.47 (t, 8.8 Hz, 2H), 3.09 (t, 8.8 Hz, 2H), 7.38 (dd, J = 8.8, 2.2 Hz, 1H), 7.77 (d, J = 8.8 Hz, 1H), 8.13 (d, J = 2.2 Hz, 1H), 8.22 (s, 1H); ¹³C NMR (D₂O/NaOD): δ 31.9, 39.9, 124.0, 129.1, 130.0, 131.5, 134.6, 135.7, 136.8, 142.8, 158.0, 186.2. Evaporation of the filtrate gives (IV) hydrochloride, 19%. Treatment of this salt with 1,2-epoxypropane lead to acid (IV), m.p. 450–452 K (D₂O, NaOD). ¹H NMR (δ p.p.m.): 2.58 (t, J = 7.9 Hz, 2H), 3.03 (t, J = 7.9 Hz, 2H), 7.17 (s, 1H), 7.31 (d, J = 8.5 Hz, 1H), 7.44 (s, 1H), 7.63 (d, J = 8.5 Hz, 1H), 8.72 (s, 1H); ¹³C NMR (δ p.p.m.): 31.9, 39.9, 12, 4.1, 129.1, 130.0, 131.5, 134.7, 135.7, 136.8, 142.8, 158.0, 186.2.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: PLATON (Spek, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON; software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. ORTEPIII (Burnett & Johnson, 1996) representation of compound (VI), with ellipsoids at the 50% probability level.
	Fig. 2. Crystal packing showing the stacked π–π interactions [symmetry code: (i) x,y,z; (ii) −x, 1 − y, −z; (iii) 1 − x, 2 − y, −z].

8,8'-dichloro-1,1',5,5'-tetrahydro-10,10'-bipyrrolo[1,2-b] isoquinolin-3,3'(2H,2'H)-dione top

Crystal data top

C₂₄H₁₈Cl₂N₂O₂	F(000) = 904
M_r = 437.30	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 24 reflections
a = 8.113 (1) Å	θ = 32–45°
b = 12.089 (1) Å	µ = 3.16 mm⁻¹
c = 20.181 (2) Å	T = 293 K
β = 92.79 (3)°	Prism, yellow
V = 1977.0 (4) Å³	0.32 × 0.16 × 0.10 mm
Z = 4

Data collection top

Nonius CAD-4 diffractometer	3055 reflections with I > 2σ(I)
Radiation source: long fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 71.9°, θ_min = 4.3°
θ/q2θ scans	h = −10→2
Absorption correction: analytical (Alcock, 1970)	k = 0→14
T_min = 0.432, T_max = 0.743	l = −24→24
6211 measured reflections	3 standard reflections every 200 reflections
3864 independent reflections	intensity decay: 4%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.066P)² + 0.791P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₄H₁₈Cl₂N₂O₂	V = 1977.0 (4) Å³
M_r = 437.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.113 (1) Å	µ = 3.16 mm⁻¹
b = 12.089 (1) Å	T = 293 K
c = 20.181 (2) Å	0.32 × 0.16 × 0.10 mm
β = 92.79 (3)°

Data collection top

Nonius CAD-4 diffractometer	3055 reflections with I > 2σ(I)
Absorption correction: analytical (Alcock, 1970)	R_int = 0.014
T_min = 0.432, T_max = 0.743	3 standard reflections every 200 reflections
6211 measured reflections	intensity decay: 4%
3864 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.64 e Å⁻³
3864 reflections	Δρ_min = −0.44 e Å⁻³
271 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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.

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

	x	y	z	U_iso*/U_eq
Cl34	0.38303 (10)	0.75010 (6)	−0.13875 (3)	0.0821 (3)
Cl14	−0.37369 (10)	0.64263 (7)	0.02067 (4)	0.0923 (3)
O15	0.5730 (3)	0.4899 (2)	0.22826 (13)	0.1124 (8)
O35	0.0581 (3)	1.20184 (14)	0.16812 (10)	0.0787 (5)
N26	0.1280 (2)	1.03773 (13)	0.12151 (9)	0.0501 (4)
N6	0.3809 (3)	0.59217 (15)	0.16983 (10)	0.0641 (5)
C31	0.1943 (3)	0.85067 (15)	0.09537 (10)	0.0467 (5)
C13	−0.0627 (3)	0.67889 (18)	0.06927 (11)	0.0573 (6)
H13	−0.0828	0.7525	0.0582	0.069*
C10	0.3516 (3)	0.70229 (17)	0.15084 (11)	0.0548 (5)
C29	0.0640 (4)	0.9102 (2)	0.20386 (12)	0.0676 (6)
H29A	0.1472	0.8824	0.2358	0.081*
H29B	−0.0281	0.8590	0.2013	0.081*
C30	0.1345 (3)	0.92567 (16)	0.13695 (10)	0.0486 (5)
C33	0.2857 (3)	0.81184 (17)	−0.01868 (11)	0.0518 (5)
H33	0.2830	0.7365	−0.0096	0.062*
C21	0.3318 (3)	0.84755 (18)	−0.07967 (11)	0.0564 (5)
C12	0.0885 (3)	0.64865 (16)	0.09836 (10)	0.0523 (5)
C32	0.2430 (2)	0.88740 (15)	0.02971 (10)	0.0454 (4)
C11	0.2164 (3)	0.73258 (16)	0.11550 (11)	0.0506 (5)
C23	0.2956 (3)	1.03369 (18)	−0.04684 (12)	0.0582 (6)
H23	0.2997	1.1089	−0.0564	0.070*
C9	0.4932 (3)	0.7706 (2)	0.17792 (13)	0.0671 (6)
H9A	0.4555	0.8264	0.2082	0.081*
H9B	0.5485	0.8069	0.1423	0.081*
C28	0.0071 (4)	1.0261 (2)	0.22320 (13)	0.0738 (7)
H28A	−0.1120	1.0286	0.2252	0.089*
H28B	0.0562	1.0472	0.2661	0.089*
C8	0.6083 (4)	0.6891 (3)	0.21414 (14)	0.0778 (8)
H8A	0.7150	0.6878	0.1945	0.093*
H8B	0.6238	0.7088	0.2606	0.093*
C4	0.1176 (3)	0.53706 (17)	0.11382 (12)	0.0614 (6)
C24	0.2457 (3)	1.00078 (16)	0.01429 (10)	0.0479 (5)
C1	−0.1836 (3)	0.6009 (2)	0.05652 (13)	0.0657 (6)
C3	−0.0082 (4)	0.46050 (18)	0.10093 (14)	0.0756 (8)
H3	0.0100	0.3866	0.1117	0.091*
C25	0.2023 (3)	1.08603 (17)	0.06466 (13)	0.0627 (6)
H25A	0.3014	1.1256	0.0794	0.075*
H25B	0.1262	1.1391	0.0440	0.075*
C2	−0.1591 (4)	0.4919 (2)	0.07247 (14)	0.0766 (8)
H2	−0.2424	0.4401	0.0643	0.092*
C22	0.3397 (3)	0.9586 (2)	−0.09461 (12)	0.0631 (6)
H22	0.3738	0.9824	−0.1356	0.076*
C5	0.2815 (4)	0.5002 (2)	0.14315 (15)	0.0791 (8)
H5A	0.2641	0.4475	0.1784	0.095*
H5B	0.3415	0.4628	0.1093	0.095*
C27	0.0639 (3)	1.10198 (19)	0.16994 (12)	0.0599 (6)
C7	0.5242 (4)	0.5789 (2)	0.20656 (14)	0.0770 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl34	0.1194 (6)	0.0595 (4)	0.0702 (4)	−0.0090 (4)	0.0330 (4)	−0.0114 (3)
Cl14	0.0816 (5)	0.0773 (5)	0.1172 (6)	−0.0204 (4)	−0.0026 (4)	−0.0196 (4)
O15	0.1234 (19)	0.0840 (15)	0.1296 (19)	0.0358 (14)	0.0028 (15)	0.0475 (14)
O35	0.1103 (15)	0.0419 (9)	0.0839 (12)	0.0167 (9)	0.0054 (11)	−0.0100 (8)
N26	0.0621 (11)	0.0306 (8)	0.0578 (10)	0.0001 (7)	0.0034 (8)	−0.0003 (7)
N6	0.0870 (14)	0.0412 (10)	0.0650 (11)	0.0135 (9)	0.0146 (10)	0.0150 (9)
C31	0.0563 (11)	0.0291 (9)	0.0548 (11)	−0.0039 (8)	0.0035 (9)	0.0037 (8)
C13	0.0756 (15)	0.0349 (10)	0.0624 (13)	−0.0069 (10)	0.0141 (11)	−0.0043 (9)
C10	0.0764 (15)	0.0368 (10)	0.0521 (11)	0.0045 (10)	0.0127 (11)	0.0077 (9)
C29	0.0916 (18)	0.0515 (13)	0.0610 (13)	−0.0030 (12)	0.0182 (12)	0.0006 (11)
C30	0.0581 (12)	0.0341 (10)	0.0535 (11)	−0.0044 (9)	0.0017 (9)	0.0027 (8)
C33	0.0646 (13)	0.0317 (10)	0.0597 (12)	−0.0056 (9)	0.0081 (10)	0.0020 (9)
C21	0.0663 (14)	0.0452 (11)	0.0585 (12)	−0.0029 (10)	0.0099 (10)	−0.0023 (10)
C12	0.0766 (15)	0.0292 (9)	0.0529 (11)	−0.0050 (9)	0.0196 (10)	0.0004 (8)
C32	0.0501 (11)	0.0314 (9)	0.0546 (11)	−0.0044 (8)	0.0023 (9)	0.0041 (8)
C11	0.0710 (14)	0.0288 (9)	0.0527 (11)	−0.0008 (9)	0.0114 (10)	0.0043 (8)
C23	0.0704 (14)	0.0368 (11)	0.0679 (14)	0.0003 (10)	0.0099 (11)	0.0132 (10)
C9	0.0784 (17)	0.0569 (14)	0.0657 (14)	0.0038 (12)	−0.0001 (12)	0.0064 (11)
C28	0.0959 (19)	0.0598 (15)	0.0667 (15)	0.0040 (14)	0.0157 (14)	−0.0053 (12)
C8	0.0796 (18)	0.085 (2)	0.0693 (16)	0.0173 (15)	0.0052 (13)	0.0117 (14)
C4	0.0948 (18)	0.0296 (10)	0.0618 (13)	0.0015 (11)	0.0240 (12)	0.0024 (9)
C24	0.0516 (11)	0.0319 (9)	0.0601 (12)	−0.0011 (8)	0.0025 (9)	0.0064 (8)
C1	0.0800 (16)	0.0491 (13)	0.0693 (14)	−0.0145 (12)	0.0174 (12)	−0.0132 (11)
C3	0.124 (2)	0.0275 (10)	0.0779 (16)	−0.0110 (13)	0.0325 (17)	−0.0016 (10)
C25	0.0842 (16)	0.0320 (10)	0.0733 (14)	−0.0026 (10)	0.0177 (12)	0.0042 (10)
C2	0.104 (2)	0.0452 (13)	0.0822 (18)	−0.0265 (14)	0.0233 (16)	−0.0123 (12)
C22	0.0798 (16)	0.0524 (13)	0.0581 (13)	−0.0046 (11)	0.0138 (11)	0.0115 (11)
C5	0.114 (2)	0.0333 (11)	0.0918 (19)	0.0117 (13)	0.0237 (17)	0.0100 (12)
C27	0.0692 (14)	0.0468 (12)	0.0634 (13)	0.0066 (11)	−0.0011 (11)	−0.0075 (10)
C7	0.0917 (19)	0.0699 (17)	0.0709 (16)	0.0243 (15)	0.0178 (14)	0.0227 (13)

Geometric parameters (Å, º) top

Cl34—C21	1.741 (2)	C12—C11	1.480 (3)
Cl14—C1	1.746 (3)	C32—C24	1.406 (3)
O15—C7	1.220 (3)	C23—C24	1.376 (3)
O35—C27	1.209 (3)	C23—C22	1.384 (3)
N26—C27	1.370 (3)	C23—H23	0.9300
N26—C30	1.391 (2)	C9—C8	1.519 (4)
N26—C25	1.445 (3)	C9—H9A	0.9700
N6—C7	1.358 (4)	C9—H9B	0.9700
N6—C10	1.402 (3)	C28—C27	1.502 (4)
N6—C5	1.461 (4)	C28—H28A	0.9700
C31—C30	1.342 (3)	C28—H28B	0.9700
C31—C32	1.470 (3)	C8—C7	1.501 (4)
C31—C11	1.493 (3)	C8—H8A	0.9700
C13—C1	1.376 (3)	C8—H8B	0.9700
C13—C12	1.383 (3)	C4—C3	1.392 (4)
C13—H13	0.9300	C4—C5	1.497 (4)
C10—C11	1.330 (3)	C24—C25	1.502 (3)
C10—C9	1.496 (3)	C1—C2	1.368 (4)
C29—C30	1.503 (3)	C3—C2	1.380 (4)
C29—C28	1.531 (4)	C3—H3	0.9300
C29—H29A	0.9700	C25—H25A	0.9700
C29—H29B	0.9700	C25—H25B	0.9700
C33—C21	1.373 (3)	C2—H2	0.9300
C33—C32	1.393 (3)	C22—H22	0.9300
C33—H33	0.9300	C5—H5A	0.9700
C21—C22	1.378 (3)	C5—H5B	0.9700
C12—C4	1.402 (3)

C27—N26—C30	113.82 (18)	C27—C28—C29	105.6 (2)
C27—N26—C25	121.64 (18)	C27—C28—H28A	110.6
C30—N26—C25	123.98 (18)	C29—C28—H28A	110.6
C7—N6—C10	113.0 (2)	C27—C28—H28B	110.6
C7—N6—C5	123.6 (2)	C29—C28—H28B	110.6
C10—N6—C5	122.6 (2)	H28A—C28—H28B	108.7
C30—C31—C32	118.74 (17)	C7—C8—C9	105.1 (2)
C30—C31—C11	121.21 (18)	C7—C8—H8A	110.7
C32—C31—C11	120.02 (17)	C9—C8—H8A	110.7
C1—C13—C12	120.5 (2)	C7—C8—H8B	110.7
C1—C13—H13	119.7	C9—C8—H8B	110.7
C12—C13—H13	119.7	H8A—C8—H8B	108.8
C11—C10—N6	122.2 (2)	C3—C4—C12	119.0 (3)
C11—C10—C9	130.0 (2)	C3—C4—C5	120.3 (2)
N6—C10—C9	107.9 (2)	C12—C4—C5	120.7 (2)
C30—C29—C28	104.35 (19)	C23—C24—C32	119.3 (2)
C30—C29—H29A	110.9	C23—C24—C25	119.84 (18)
C28—C29—H29A	110.9	C32—C24—C25	120.83 (19)
C30—C29—H29B	110.9	C2—C1—C13	121.5 (3)
C28—C29—H29B	110.9	C2—C1—Cl14	119.4 (2)
H29A—C29—H29B	108.9	C13—C1—Cl14	119.1 (2)
C31—C30—N26	121.93 (19)	C2—C3—C4	121.5 (2)
C31—C30—C29	129.98 (19)	C2—C3—H3	119.3
N26—C30—C29	108.08 (18)	C4—C3—H3	119.3
C21—C33—C32	120.66 (19)	N26—C25—C24	112.39 (17)
C21—C33—H33	119.7	N26—C25—H25A	109.1
C32—C33—H33	119.7	C24—C25—H25A	109.1
C33—C21—C22	121.3 (2)	N26—C25—H25B	109.1
C33—C21—Cl34	119.05 (17)	C24—C25—H25B	109.1
C22—C21—Cl34	119.61 (18)	H25A—C25—H25B	107.9
C13—C12—C4	119.0 (2)	C1—C2—C3	118.6 (2)
C13—C12—C11	121.01 (18)	C1—C2—H2	120.7
C4—C12—C11	120.0 (2)	C3—C2—H2	120.7
C33—C32—C24	118.49 (19)	C21—C22—C23	118.0 (2)
C33—C32—C31	121.39 (17)	C21—C22—H22	121.0
C24—C32—C31	120.12 (18)	C23—C22—H22	121.0
C10—C11—C12	119.13 (19)	N6—C5—C4	112.52 (19)
C10—C11—C31	119.6 (2)	N6—C5—H5A	109.1
C12—C11—C31	121.2 (2)	C4—C5—H5A	109.1
C24—C23—C22	122.2 (2)	N6—C5—H5B	109.1
C24—C23—H23	118.9	C4—C5—H5B	109.1
C22—C23—H23	118.9	H5A—C5—H5B	107.8
C10—C9—C8	105.2 (2)	O35—C27—N26	124.1 (2)
C10—C9—H9A	110.7	O35—C27—C28	128.2 (2)
C8—C9—H9A	110.7	N26—C27—C28	107.72 (19)
C10—C9—H9B	110.7	O15—C7—N6	123.7 (3)
C8—C9—H9B	110.7	O15—C7—C8	127.4 (3)
H9A—C9—H9B	108.8	N6—C7—C8	108.9 (2)

C7—N6—C10—C11	−178.9 (2)	C13—C12—C4—C3	−1.6 (3)
C5—N6—C10—C11	10.8 (3)	C11—C12—C4—C3	176.1 (2)
C7—N6—C10—C9	0.4 (3)	C13—C12—C4—C5	177.9 (2)
C5—N6—C10—C9	−169.9 (2)	C11—C12—C4—C5	−4.5 (3)
C32—C31—C30—N26	−4.5 (3)	C22—C23—C24—C32	1.6 (4)
C11—C31—C30—N26	173.7 (2)	C22—C23—C24—C25	178.8 (2)
C32—C31—C30—C29	174.7 (2)	C33—C32—C24—C23	−2.2 (3)
C11—C31—C30—C29	−7.1 (4)	C31—C32—C24—C23	178.40 (19)
C27—N26—C30—C31	−179.7 (2)	C33—C32—C24—C25	−179.5 (2)
C25—N26—C30—C31	−8.2 (3)	C31—C32—C24—C25	1.1 (3)
C27—N26—C30—C29	0.9 (3)	C12—C13—C1—C2	0.5 (4)
C25—N26—C30—C29	172.5 (2)	C12—C13—C1—Cl14	179.24 (17)
C28—C29—C30—C31	−176.2 (2)	C12—C4—C3—C2	1.0 (4)
C28—C29—C30—N26	3.1 (3)	C5—C4—C3—C2	−178.5 (2)
C32—C33—C21—C22	1.0 (4)	C27—N26—C25—C24	−173.2 (2)
C32—C33—C21—Cl34	−179.65 (17)	C30—N26—C25—C24	15.9 (3)
C1—C13—C12—C4	0.9 (3)	C23—C24—C25—N26	170.8 (2)
C1—C13—C12—C11	−176.8 (2)	C32—C24—C25—N26	−12.0 (3)
C21—C33—C32—C24	1.0 (3)	C13—C1—C2—C3	−1.1 (4)
C21—C33—C32—C31	−179.6 (2)	Cl14—C1—C2—C3	−179.85 (19)
C30—C31—C32—C33	−171.6 (2)	C4—C3—C2—C1	0.4 (4)
C11—C31—C32—C33	10.1 (3)	C33—C21—C22—C23	−1.7 (4)
C30—C31—C32—C24	7.7 (3)	Cl34—C21—C22—C23	178.96 (19)
C11—C31—C32—C24	−170.5 (2)	C24—C23—C22—C21	0.4 (4)
N6—C10—C11—C12	3.1 (3)	C7—N6—C5—C4	171.0 (2)
C9—C10—C11—C12	−176.0 (2)	C10—N6—C5—C4	−19.8 (3)
N6—C10—C11—C31	−178.47 (19)	C3—C4—C5—N6	−164.3 (2)
C9—C10—C11—C31	2.4 (4)	C12—C4—C5—N6	16.3 (3)
C13—C12—C11—C10	171.6 (2)	C30—N26—C27—O35	174.8 (2)
C4—C12—C11—C10	−6.1 (3)	C25—N26—C27—O35	3.0 (4)
C13—C12—C11—C31	−6.8 (3)	C30—N26—C27—C28	−4.7 (3)
C4—C12—C11—C31	175.52 (19)	C25—N26—C27—C28	−176.5 (2)
C30—C31—C11—C10	−82.9 (3)	C29—C28—C27—O35	−173.1 (3)
C32—C31—C11—C10	95.2 (2)	C29—C28—C27—N26	6.4 (3)
C30—C31—C11—C12	95.5 (3)	C10—N6—C7—O15	179.8 (3)
C32—C31—C11—C12	−86.4 (3)	C5—N6—C7—O15	−10.0 (4)
C11—C10—C9—C8	179.6 (2)	C10—N6—C7—C8	−0.9 (3)
N6—C10—C9—C8	0.4 (3)	C5—N6—C7—C8	169.2 (2)
C30—C29—C28—C27	−5.6 (3)	C9—C8—C7—O15	−179.7 (3)
C10—C9—C8—C7	−0.9 (3)	C9—C8—C7—N6	1.1 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈Cl₂N₂O₂
M_r	437.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.113 (1), 12.089 (1), 20.181 (2)
β (°)	92.79 (3)
V (Å³)	1977.0 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.32 × 0.16 × 0.10

Data collection
Diffractometer	Nonius CAD-4 diffractometer
Absorption correction	Analytical (Alcock, 1970)
T_min, T_max	0.432, 0.743
No. of measured, independent and observed [I > 2σ(I)] reflections	6211, 3864, 3055
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.04
No. of reflections	3864
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.44

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1992), CAD-4 EXPRESS, PLATON (Spek, 2003), SIR97 (Altomare et al., 1997), SHELXL97 (Sheldrick, 1997), PLATON, SHELXL97.

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