5′′-(4-Chloro­benzyl­idene)-4′-(4-chloro­phen­yl)-1′′-methyl-5′-phenyl­acenaph­thene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-piperidine-2,4′′-dione

Athimoolam, S.; Kumar, R.R.; Vijaya, K.; Kannan, R.S.; Perumal, S.

doi:10.1107/S1600536807055109

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5′′-(4-Chlorobenzylidene)-4′-(4-chlorophenyl)-1′′-methyl-5′-phenylacenaphthene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-piperidine-2,4′′-dione

S. Athimoolam, R. R. Kumar, K. Vijaya, R. S. Kannan and S. Perumal

In the title compound, C₃₉H₃₀Cl₂N₂O₂, the central six-membered piperidinone ring adopts a distorted half-chair conformation and the five-membered pyrrolidine ring is in a twist conformation. The crystal structure is stabilized by C—H

O and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055109/sj2401sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055109/sj2401Isup2.hkl Contains datablock I

CCDC reference: 672888

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.142
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1N    ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C15    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C28    = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

1,3-Dipolar cycloadditions form a subject of intensive research in organic synthesis in view of their great synthetic potential (Karthikeyan et al., 2007). In particular, the cycloaddition of nonstabilized azomethine ylides with olefins represents one of the most convergent approaches for the construction of pyrrolidines (Boruah et al., 2007), which are prevalent in a variety of biologically active compounds (Watson et al., 2001) and find utility in the treatment of diseases such as diabetes (Horri et al., 1986). Acenaphthenequinone is a versatile precursor for azomethine ylide cycloaddition as it reacts with various α-amino acids generating reactive 1,3-dipoles (Babu & Raghunathan, 2007). Synthesis of spiro compounds have drawn considerable attention of the chemists, in view of their very good antimycobacterial activity. The importance of spiro-compounds and nitrogen heterocycles led us to synthesize novel spiro heterocycles via 1,3-dipoar cycloaddition of azomethine ylides (Chande et al., 2005).

The slightly twisted conformation of the 5-membered pyrrolidine ring is confirmed through the puckering analysis [θ₂ = 0.420 (3) Å and π₂ = 47.5 (4)°; Cremer & Pople, 1975] and the 6-membered piperidinone ring adopts a distorted half-chair conformation [θ₂ = 0.273 (3) Å, π₂ = 62.7 (6)° and θ₃ = 0.467 (3) Å] (Fig. 1). The dihedral angle between the chlorophenyl rings is observed to be 73.6 (1)° and these rings make angles of 71.5 (1) and 23.1 (2) ° with the phenyl ring (C9/C14). Further, the acenaphthene group (C28/C39) is oriented at an angle of 35.1 (1)° to the (C9/C14) phenyl ring.

The crystal structue of (I) features two intramolecular and two intermolecular C—H···O hydrogen bonds [Fig 2; Table 1]. It is further stabilized by an intermolecular C32—H32···π interaction, with the C1—C6 benzene ring (centroid Cg) (Desiraju & Steiner, 1999).

Related literature top

For the pharmacological importance of similar compounds, see: Babu & Raghunathan (2007); Boruah et al. (2007); Chande et al. (2005); Horri et al. (1986); Karthikeyan et al. (2007); Watson et al. (2001). For ring puckering analysis, see: Cremer & Pople (1975) and for hydrogen-bonding interactions, see: Desiraju & Steiner, (1999).

Experimental top

A mixture of 1-methyl-3,5-bis[(E)-4-chlorophenylmethylidene]tetrahydro-4(1H)-pyridinone 1 mmol), acenaphthenequinone (1 mmol) and phenylglycine (1 mmol) was dissolved in methanol (10 ml) and refluxed for 1 h. After completion of the reaction evident from TLC, the mixture was poured into water (50 ml), the precipitated solid filtered and washed with water (100 ml) to obtain pure 4-(4-chlorophenyl)-5-phenylpyrrolo-(spiro[2.2'']-acenaphthene-1''-one)- spiro[3.3']-5'-(4-chlorophenylmethylid-ene)-1'-methyltetrahydro-4'- (1H)-pyridinone as pale yellow solid. The product was recrystallized from methanol/ethyl acetate solution (1:1).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC (Bruker, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC (Bruker, 2000).

Figures top

	Fig. 1. The molecular structure of the title compound (I) with the numbering scheme for the atoms and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the molecules, viewed down the b-axis.

4-(4-Chlorophenyl)-5-phenylpyrrolo-(spiro[2.2'']-acenaphthene- 1''-one)-spiro[3.3']-5'-(4-chlorophenylmethylidene)-1'- methyltetrahydro-4'-(1H)-pyridinone top

Crystal data top

C₃₉H₃₀Cl₂N₂O₂	Z = 2
M_r = 629.55	F(000) = 656
Triclinic, P1	D_x = 1.325 Mg m⁻³
Hall symbol: -P 1	Melting point: 190 K
a = 9.5567 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0442 (11) Å	Cell parameters from 25 reflections
c = 14.8593 (15) Å	θ = 10.3–14.3°
α = 76.025 (11)°	µ = 0.24 mm⁻¹
β = 75.445 (9)°	T = 293 K
γ = 76.220 (8)°	Block, pale yellow
V = 1577.5 (3) Å³	0.24 × 0.15 × 0.14 mm

Data collection top

Nonius MACH3 diffractometer	3434 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω–2θ scans	h = −1→11
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.947, T_max = 0.973	l = −17→17
6631 measured reflections	3 standard reflections every 60 min
5538 independent reflections	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ^2^(F_o^2^) + (0.0646P)^2^ + 0.6033P] where P = (F_o^2^ + 2F_c^2^)/3
5538 reflections	(Δ/σ)_max < 0.001
406 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₉H₃₀Cl₂N₂O₂	γ = 76.220 (8)°
M_r = 629.55	V = 1577.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.5567 (6) Å	Mo Kα radiation
b = 12.0442 (11) Å	µ = 0.24 mm⁻¹
c = 14.8593 (15) Å	T = 293 K
α = 76.025 (11)°	0.24 × 0.15 × 0.14 mm
β = 75.445 (9)°

Data collection top

Nonius MACH3 diffractometer	3434 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.947, T_max = 0.973	3 standard reflections every 60 min
6631 measured reflections	intensity decay: none
5538 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
5538 reflections	Δρ_min = −0.29 e Å⁻³
406 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl1	0.39281 (11)	0.66064 (7)	0.25272 (8)	0.0971 (3)
Cl2	0.66042 (13)	−0.41648 (10)	−0.12138 (9)	0.1138 (4)
O1	0.8216 (2)	0.13701 (16)	0.10490 (13)	0.0599 (5)
O2	0.6391 (3)	−0.11023 (17)	0.46785 (14)	0.0694 (6)
N2	0.5209 (2)	−0.03202 (17)	0.29297 (15)	0.0486 (5)
N1	0.8833 (3)	0.01394 (18)	0.37587 (17)	0.0608 (6)
H1N	0.9614	−0.0209	0.3972	0.073*
C15	0.7150 (3)	0.07564 (19)	0.26833 (17)	0.0439 (6)
C7	0.7663 (3)	0.1783 (2)	0.28857 (18)	0.0460 (6)
H7	0.8590	0.1876	0.2434	0.055*
C20	0.7480 (3)	0.0734 (2)	0.16348 (18)	0.0448 (6)
C6	0.6653 (3)	0.2963 (2)	0.27850 (18)	0.0453 (6)
C22	0.7278 (3)	−0.1436 (2)	0.01626 (18)	0.0491 (6)
C24	0.5669 (3)	−0.2443 (2)	−0.0226 (2)	0.0587 (7)
H24	0.4724	−0.2546	−0.0197	0.070*
C19	0.6821 (3)	−0.0111 (2)	0.13483 (17)	0.0440 (6)
C21	0.7584 (3)	−0.0567 (2)	0.05952 (19)	0.0502 (6)
H21	0.8448	−0.0290	0.0297	0.060*
C18	0.5404 (3)	−0.0415 (2)	0.19504 (18)	0.0524 (7)
H18A	0.4593	0.0098	0.1690	0.063*
H18B	0.5373	−0.1206	0.1928	0.063*
C39	0.8791 (3)	−0.2214 (2)	0.2780 (2)	0.0535 (7)
C4	0.6137 (4)	0.4930 (2)	0.1905 (2)	0.0618 (8)
H4	0.6370	0.5491	0.1368	0.074*
C38	0.9203 (3)	−0.1123 (2)	0.26017 (19)	0.0515 (7)
C16	0.5501 (3)	0.0771 (2)	0.30363 (19)	0.0480 (6)
H16A	0.5211	0.0845	0.3696	0.058*
H16B	0.4946	0.1427	0.2669	0.058*
C28	0.8110 (3)	−0.0362 (2)	0.32360 (18)	0.0489 (6)
C1	0.5444 (3)	0.3265 (2)	0.3482 (2)	0.0564 (7)
H1	0.5195	0.2708	0.4018	0.068*
C9	0.8973 (3)	0.2003 (2)	0.4117 (2)	0.0551 (7)
C23	0.5880 (3)	−0.1606 (2)	0.01949 (19)	0.0527 (7)
H23	0.5065	−0.1146	0.0507	0.063*
C8	0.8048 (3)	0.1311 (2)	0.38675 (19)	0.0517 (7)
H8	0.7143	0.1268	0.4353	0.062*
C3	0.4972 (3)	0.5199 (2)	0.2609 (2)	0.0597 (8)
C2	0.4596 (3)	0.4379 (2)	0.3397 (2)	0.0622 (8)
H2	0.3783	0.4567	0.3869	0.075*
C5	0.6977 (3)	0.3811 (2)	0.1992 (2)	0.0541 (7)
H5	0.7772	0.3629	0.1507	0.065*
C34	0.9571 (4)	−0.3103 (3)	0.2282 (2)	0.0674 (9)
C29	0.7140 (3)	−0.1243 (2)	0.3912 (2)	0.0537 (7)
C37	1.0424 (3)	−0.0926 (3)	0.1927 (2)	0.0654 (8)
H37	1.0748	−0.0226	0.1814	0.078*
C30	0.7584 (4)	−0.2334 (2)	0.3522 (2)	0.0566 (7)
C31	0.7090 (4)	−0.3377 (2)	0.3807 (2)	0.0706 (9)
H31	0.6281	−0.3476	0.4300	0.085*
C12	1.0636 (5)	0.3326 (3)	0.4550 (3)	0.0874 (12)
H12	1.1187	0.3780	0.4689	0.105*
C10	0.8448 (4)	0.2578 (3)	0.4865 (2)	0.0706 (9)
H10	0.7510	0.2530	0.5229	0.085*
C25	0.6862 (4)	−0.3114 (3)	−0.0683 (2)	0.0665 (8)
C27	0.8453 (3)	−0.2117 (3)	−0.0329 (2)	0.0739 (9)
H27	0.9401	−0.2006	−0.0378	0.089*
C17	0.3784 (4)	−0.0545 (3)	0.3471 (2)	0.0766 (10)
H17A	0.3686	−0.0478	0.4116	0.115*
H17B	0.3698	−0.1318	0.3454	0.115*
H17C	0.3023	0.0011	0.3203	0.115*
C14	1.0365 (4)	0.2101 (3)	0.3594 (3)	0.0808 (10)
H14	1.0753	0.1713	0.3089	0.097*
C13	1.1201 (4)	0.2763 (4)	0.3803 (3)	0.0940 (12)
H13	1.2135	0.2825	0.3440	0.113*
C11	0.9284 (5)	0.3229 (3)	0.5089 (3)	0.0831 (11)
H11	0.8918	0.3596	0.5607	0.100*
C32	0.7860 (5)	−0.4286 (3)	0.3325 (3)	0.0830 (11)
H32	0.7550	−0.4998	0.3512	0.100*
C26	0.8260 (4)	−0.2958 (3)	−0.0751 (3)	0.0860 (11)
H26	0.9067	−0.3412	−0.1075	0.103*
C33	0.9037 (5)	−0.4166 (3)	0.2597 (3)	0.0861 (11)
H33	0.9503	−0.4793	0.2300	0.103*
C36	1.1187 (4)	−0.1793 (3)	0.1403 (3)	0.0833 (10)
H36	1.1999	−0.1644	0.0926	0.100*
C35	1.0774 (4)	−0.2846 (3)	0.1571 (3)	0.0845 (11)
H35	1.1303	−0.3397	0.1207	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1059 (7)	0.0439 (4)	0.1351 (9)	0.0062 (4)	−0.0465 (6)	−0.0028 (5)
Cl2	0.1153 (8)	0.1074 (8)	0.1551 (10)	−0.0216 (6)	−0.0370 (7)	−0.0831 (8)
O1	0.0768 (14)	0.0599 (12)	0.0485 (11)	−0.0347 (11)	−0.0094 (10)	−0.0030 (9)
O2	0.1019 (17)	0.0576 (12)	0.0456 (12)	−0.0180 (11)	−0.0145 (12)	−0.0022 (9)
N2	0.0609 (14)	0.0387 (11)	0.0464 (13)	−0.0177 (10)	−0.0054 (11)	−0.0065 (9)
N1	0.0783 (17)	0.0404 (12)	0.0738 (16)	−0.0015 (11)	−0.0435 (14)	−0.0105 (11)
C15	0.0549 (16)	0.0339 (12)	0.0444 (14)	−0.0091 (11)	−0.0159 (12)	−0.0038 (10)
C7	0.0567 (16)	0.0375 (13)	0.0473 (15)	−0.0121 (12)	−0.0170 (13)	−0.0050 (11)
C20	0.0491 (15)	0.0385 (13)	0.0457 (15)	−0.0075 (12)	−0.0141 (12)	−0.0022 (11)
C6	0.0564 (16)	0.0357 (13)	0.0503 (15)	−0.0131 (12)	−0.0207 (13)	−0.0061 (11)
C22	0.0522 (16)	0.0493 (15)	0.0480 (15)	−0.0113 (13)	−0.0116 (13)	−0.0105 (12)
C24	0.0622 (18)	0.0606 (17)	0.0612 (18)	−0.0147 (15)	−0.0217 (15)	−0.0144 (14)
C19	0.0516 (15)	0.0407 (13)	0.0431 (14)	−0.0131 (11)	−0.0159 (12)	−0.0034 (11)
C21	0.0554 (17)	0.0494 (15)	0.0505 (16)	−0.0187 (13)	−0.0132 (13)	−0.0069 (12)
C18	0.0614 (17)	0.0486 (15)	0.0519 (16)	−0.0198 (13)	−0.0114 (13)	−0.0098 (12)
C39	0.0692 (19)	0.0420 (14)	0.0536 (17)	0.0012 (13)	−0.0305 (15)	−0.0099 (12)
C4	0.081 (2)	0.0408 (15)	0.0654 (19)	−0.0191 (15)	−0.0290 (18)	0.0086 (13)
C38	0.0612 (18)	0.0423 (14)	0.0514 (16)	−0.0013 (13)	−0.0232 (14)	−0.0059 (12)
C16	0.0607 (17)	0.0362 (13)	0.0479 (15)	−0.0107 (12)	−0.0128 (13)	−0.0066 (11)
C28	0.0670 (18)	0.0355 (13)	0.0474 (15)	−0.0110 (12)	−0.0210 (13)	−0.0029 (11)
C1	0.0693 (19)	0.0379 (14)	0.0622 (18)	−0.0132 (13)	−0.0177 (16)	−0.0027 (13)
C9	0.072 (2)	0.0417 (14)	0.0577 (17)	−0.0094 (13)	−0.0313 (16)	−0.0041 (13)
C23	0.0532 (17)	0.0526 (15)	0.0561 (16)	−0.0063 (13)	−0.0169 (13)	−0.0155 (13)
C8	0.0682 (18)	0.0390 (13)	0.0520 (16)	−0.0111 (13)	−0.0221 (14)	−0.0055 (12)
C3	0.066 (2)	0.0378 (14)	0.082 (2)	−0.0095 (13)	−0.0353 (18)	−0.0039 (14)
C2	0.0610 (18)	0.0472 (16)	0.080 (2)	−0.0084 (14)	−0.0171 (16)	−0.0132 (15)
C5	0.0671 (18)	0.0440 (15)	0.0539 (16)	−0.0175 (13)	−0.0186 (14)	−0.0011 (12)
C34	0.079 (2)	0.0525 (18)	0.079 (2)	0.0094 (16)	−0.0411 (19)	−0.0228 (16)
C29	0.077 (2)	0.0399 (14)	0.0447 (16)	−0.0096 (13)	−0.0219 (15)	−0.0011 (12)
C37	0.0594 (19)	0.0588 (18)	0.073 (2)	−0.0011 (15)	−0.0200 (17)	−0.0062 (16)
C30	0.082 (2)	0.0362 (14)	0.0572 (17)	−0.0094 (13)	−0.0330 (16)	−0.0020 (12)
C31	0.100 (2)	0.0431 (16)	0.077 (2)	−0.0200 (16)	−0.0420 (19)	0.0045 (15)
C12	0.106 (3)	0.070 (2)	0.111 (3)	−0.028 (2)	−0.066 (3)	−0.008 (2)
C10	0.105 (3)	0.0562 (17)	0.0602 (19)	−0.0328 (17)	−0.0207 (18)	−0.0078 (15)
C25	0.074 (2)	0.0631 (19)	0.074 (2)	−0.0123 (16)	−0.0220 (17)	−0.0280 (16)
C27	0.0538 (19)	0.093 (2)	0.088 (2)	−0.0225 (17)	−0.0032 (17)	−0.045 (2)
C17	0.087 (2)	0.071 (2)	0.074 (2)	−0.0421 (18)	0.0139 (19)	−0.0241 (17)
C14	0.067 (2)	0.086 (2)	0.106 (3)	−0.0006 (18)	−0.037 (2)	−0.042 (2)
C13	0.068 (2)	0.103 (3)	0.131 (3)	−0.017 (2)	−0.043 (2)	−0.034 (3)
C11	0.132 (3)	0.063 (2)	0.076 (2)	−0.035 (2)	−0.038 (2)	−0.0168 (17)
C32	0.123 (3)	0.0386 (17)	0.107 (3)	−0.0197 (19)	−0.067 (3)	−0.0030 (18)
C26	0.065 (2)	0.099 (3)	0.110 (3)	−0.0075 (19)	−0.009 (2)	−0.066 (2)
C33	0.112 (3)	0.0479 (19)	0.116 (3)	0.0064 (19)	−0.058 (3)	−0.033 (2)
C36	0.065 (2)	0.087 (3)	0.082 (2)	0.0141 (19)	−0.0155 (18)	−0.015 (2)
C35	0.082 (3)	0.077 (2)	0.091 (3)	0.027 (2)	−0.028 (2)	−0.039 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.743 (3)	C28—C29	1.575 (4)
Cl2—C25	1.735 (3)	C1—C2	1.388 (4)
O1—C20	1.211 (3)	C1—H1	0.9300
O2—C29	1.209 (3)	C9—C10	1.376 (4)
N2—C17	1.447 (3)	C9—C14	1.378 (4)
N2—C18	1.449 (3)	C9—C8	1.510 (4)
N2—C16	1.459 (3)	C23—H23	0.9300
N1—C8	1.458 (3)	C8—H8	0.9800
N1—C28	1.463 (3)	C3—C2	1.369 (4)
N1—H1N	0.8600	C2—H2	0.9300
C15—C20	1.516 (3)	C5—H5	0.9300
C15—C16	1.527 (4)	C34—C35	1.391 (5)
C15—C7	1.550 (3)	C34—C33	1.421 (5)
C15—C28	1.608 (3)	C29—C30	1.491 (4)
C7—C6	1.513 (3)	C37—C36	1.405 (5)
C7—C8	1.535 (3)	C37—H37	0.9300
C7—H7	0.9800	C30—C31	1.380 (4)
C20—C19	1.505 (3)	C31—C32	1.409 (5)
C6—C5	1.384 (4)	C31—H31	0.9300
C6—C1	1.386 (4)	C12—C11	1.354 (5)
C22—C27	1.381 (4)	C12—C13	1.367 (5)
C22—C23	1.386 (4)	C12—H12	0.9300
C22—C21	1.470 (4)	C10—C11	1.386 (5)
C24—C25	1.360 (4)	C10—H10	0.9300
C24—C23	1.384 (4)	C25—C26	1.369 (4)
C24—H24	0.9300	C27—C26	1.381 (4)
C19—C21	1.335 (4)	C27—H27	0.9300
C19—C18	1.495 (4)	C17—H17A	0.9600
C21—H21	0.9300	C17—H17B	0.9600
C18—H18A	0.9700	C17—H17C	0.9600
C18—H18B	0.9700	C14—C13	1.385 (5)
C39—C30	1.389 (4)	C14—H14	0.9300
C39—C34	1.406 (4)	C13—H13	0.9300
C39—C38	1.407 (4)	C11—H11	0.9300
C4—C3	1.359 (4)	C32—C33	1.358 (5)
C4—C5	1.389 (4)	C32—H32	0.9300
C4—H4	0.9300	C26—H26	0.9300
C38—C37	1.360 (4)	C33—H33	0.9300
C38—C28	1.512 (4)	C36—C35	1.364 (5)
C16—H16A	0.9700	C36—H36	0.9300
C16—H16B	0.9700	C35—H35	0.9300

C17—N2—C18	111.3 (2)	N1—C8—C9	112.6 (2)
C17—N2—C16	112.4 (2)	N1—C8—C7	100.4 (2)
C18—N2—C16	113.4 (2)	C9—C8—C7	114.1 (2)
C8—N1—C28	110.7 (2)	N1—C8—H8	109.8
C8—N1—H1N	124.7	C9—C8—H8	109.8
C28—N1—H1N	124.7	C7—C8—H8	109.8
C20—C15—C16	106.4 (2)	C4—C3—C2	121.1 (3)
C20—C15—C7	112.3 (2)	C4—C3—Cl1	120.4 (2)
C16—C15—C7	113.7 (2)	C2—C3—Cl1	118.6 (3)
C20—C15—C28	110.50 (19)	C3—C2—C1	119.0 (3)
C16—C15—C28	111.5 (2)	C3—C2—H2	120.5
C7—C15—C28	102.45 (18)	C1—C2—H2	120.5
C6—C7—C8	114.7 (2)	C6—C5—C4	121.2 (3)
C6—C7—C15	117.6 (2)	C6—C5—H5	119.4
C8—C7—C15	103.61 (19)	C4—C5—H5	119.4
C6—C7—H7	106.7	C35—C34—C39	116.6 (3)
C8—C7—H7	106.7	C35—C34—C33	128.6 (3)
C15—C7—H7	106.7	C39—C34—C33	114.8 (3)
O1—C20—C19	121.1 (2)	O2—C29—C30	127.8 (3)
O1—C20—C15	122.4 (2)	O2—C29—C28	124.3 (2)
C19—C20—C15	116.5 (2)	C30—C29—C28	106.6 (2)
C5—C6—C1	117.5 (2)	C38—C37—C36	119.2 (3)
C5—C6—C7	119.5 (2)	C38—C37—H37	120.4
C1—C6—C7	122.8 (2)	C36—C37—H37	120.4
C27—C22—C23	117.2 (2)	C31—C30—C39	119.8 (3)
C27—C22—C21	118.3 (3)	C31—C30—C29	132.1 (3)
C23—C22—C21	124.5 (2)	C39—C30—C29	107.9 (2)
C25—C24—C23	119.2 (3)	C30—C31—C32	117.4 (3)
C25—C24—H24	120.4	C30—C31—H31	121.3
C23—C24—H24	120.4	C32—C31—H31	121.3
C21—C19—C18	125.2 (2)	C11—C12—C13	120.7 (3)
C21—C19—C20	117.0 (2)	C11—C12—H12	119.7
C18—C19—C20	117.8 (2)	C13—C12—H12	119.7
C19—C21—C22	130.3 (3)	C9—C10—C11	121.5 (3)
C19—C21—H21	114.9	C9—C10—H10	119.2
C22—C21—H21	114.9	C11—C10—H10	119.2
N2—C18—C19	113.2 (2)	C24—C25—C26	121.2 (3)
N2—C18—H18A	108.9	C24—C25—Cl2	119.4 (2)
C19—C18—H18A	108.9	C26—C25—Cl2	119.3 (2)
N2—C18—H18B	108.9	C22—C27—C26	121.9 (3)
C19—C18—H18B	108.9	C22—C27—H27	119.0
H18A—C18—H18B	107.8	C26—C27—H27	119.0
C30—C39—C34	124.0 (3)	N2—C17—H17A	109.5
C30—C39—C38	113.1 (2)	N2—C17—H17B	109.5
C34—C39—C38	122.9 (3)	H17A—C17—H17B	109.5
C3—C4—C5	119.6 (3)	N2—C17—H17C	109.5
C3—C4—H4	120.2	H17A—C17—H17C	109.5
C5—C4—H4	120.2	H17B—C17—H17C	109.5
C37—C38—C39	118.5 (3)	C9—C14—C13	121.4 (3)
C37—C38—C28	132.1 (2)	C9—C14—H14	119.3
C39—C38—C28	109.4 (2)	C13—C14—H14	119.3
N2—C16—C15	107.9 (2)	C12—C13—C14	119.3 (4)
N2—C16—H16A	110.1	C12—C13—H13	120.4
C15—C16—H16A	110.1	C14—C13—H13	120.4
N2—C16—H16B	110.1	C12—C11—C10	119.6 (3)
C15—C16—H16B	110.1	C12—C11—H11	120.2
H16A—C16—H16B	108.4	C10—C11—H11	120.2
N1—C28—C38	112.1 (2)	C33—C32—C31	122.7 (3)
N1—C28—C29	112.1 (2)	C33—C32—H32	118.6
C38—C28—C29	102.2 (2)	C31—C32—H32	118.6
N1—C28—C15	103.73 (18)	C25—C26—C27	118.9 (3)
C38—C28—C15	114.5 (2)	C25—C26—H26	120.6
C29—C28—C15	112.6 (2)	C27—C26—H26	120.6
C6—C1—C2	121.5 (3)	C32—C33—C34	121.3 (3)
C6—C1—H1	119.2	C32—C33—H33	119.3
C2—C1—H1	119.2	C34—C33—H33	119.3
C10—C9—C14	117.5 (3)	C35—C36—C37	122.1 (4)
C10—C9—C8	121.3 (3)	C35—C36—H36	119.0
C14—C9—C8	121.3 (3)	C37—C36—H36	119.0
C24—C23—C22	121.6 (3)	C36—C35—C34	120.7 (3)
C24—C23—H23	119.2	C36—C35—H35	119.7
C22—C23—H23	119.2	C34—C35—H35	119.7

C20—C15—C7—C6	82.7 (3)	C10—C9—C8—N1	−130.0 (3)
C16—C15—C7—C6	−38.3 (3)	C14—C9—C8—N1	51.3 (4)
C28—C15—C7—C6	−158.8 (2)	C10—C9—C8—C7	116.4 (3)
C20—C15—C7—C8	−149.5 (2)	C14—C9—C8—C7	−62.3 (4)
C16—C15—C7—C8	89.5 (2)	C6—C7—C8—N1	172.6 (2)
C28—C15—C7—C8	−30.9 (2)	C15—C7—C8—N1	43.1 (3)
C16—C15—C20—O1	133.2 (2)	C6—C7—C8—C9	−66.7 (3)
C7—C15—C20—O1	8.1 (3)	C15—C7—C8—C9	163.7 (2)
C28—C15—C20—O1	−105.6 (3)	C5—C4—C3—C2	−1.1 (4)
C16—C15—C20—C19	−45.8 (3)	C5—C4—C3—Cl1	178.5 (2)
C7—C15—C20—C19	−170.8 (2)	C4—C3—C2—C1	1.5 (4)
C28—C15—C20—C19	75.4 (3)	Cl1—C3—C2—C1	−178.2 (2)
C8—C7—C6—C5	134.4 (3)	C6—C1—C2—C3	−0.5 (4)
C15—C7—C6—C5	−103.3 (3)	C1—C6—C5—C4	1.1 (4)
C8—C7—C6—C1	−41.9 (3)	C7—C6—C5—C4	−175.4 (2)
C15—C7—C6—C1	80.4 (3)	C3—C4—C5—C6	−0.2 (4)
O1—C20—C19—C21	32.7 (4)	C30—C39—C34—C35	−178.6 (3)
C15—C20—C19—C21	−148.3 (2)	C38—C39—C34—C35	−1.7 (4)
O1—C20—C19—C18	−149.9 (2)	C30—C39—C34—C33	−0.3 (4)
C15—C20—C19—C18	29.0 (3)	C38—C39—C34—C33	176.6 (3)
C18—C19—C21—C22	0.3 (4)	N1—C28—C29—O2	39.2 (4)
C20—C19—C21—C22	177.4 (2)	C38—C28—C29—O2	159.4 (3)
C27—C22—C21—C19	−152.9 (3)	C15—C28—C29—O2	−77.3 (3)
C23—C22—C21—C19	28.5 (4)	N1—C28—C29—C30	−129.1 (2)
C17—N2—C18—C19	176.1 (2)	C38—C28—C29—C30	−8.8 (3)
C16—N2—C18—C19	48.2 (3)	C15—C28—C29—C30	114.4 (2)
C21—C19—C18—N2	149.3 (2)	C39—C38—C37—C36	3.0 (4)
C20—C19—C18—N2	−27.8 (3)	C28—C38—C37—C36	−176.1 (3)
C30—C39—C38—C37	176.3 (2)	C34—C39—C30—C31	0.1 (4)
C34—C39—C38—C37	−1.0 (4)	C38—C39—C30—C31	−177.1 (3)
C30—C39—C38—C28	−4.5 (3)	C34—C39—C30—C29	175.6 (2)
C34—C39—C38—C28	178.3 (2)	C38—C39—C30—C29	−1.6 (3)
C17—N2—C16—C15	164.1 (2)	O2—C29—C30—C31	13.8 (5)
C18—N2—C16—C15	−68.6 (3)	C28—C29—C30—C31	−178.5 (3)
C20—C15—C16—N2	64.1 (2)	O2—C29—C30—C39	−161.0 (3)
C7—C15—C16—N2	−171.7 (2)	C28—C29—C30—C39	6.7 (3)
C28—C15—C16—N2	−56.5 (3)	C39—C30—C31—C32	0.4 (4)
C8—N1—C28—C38	144.7 (2)	C29—C30—C31—C32	−173.8 (3)
C8—N1—C28—C29	−101.1 (2)	C14—C9—C10—C11	−0.2 (5)
C8—N1—C28—C15	20.6 (3)	C8—C9—C10—C11	−179.0 (3)
C37—C38—C28—N1	−52.6 (4)	C23—C24—C25—C26	−1.4 (5)
C39—C38—C28—N1	128.3 (2)	C23—C24—C25—Cl2	−179.9 (2)
C37—C38—C28—C29	−172.8 (3)	C23—C22—C27—C26	−1.8 (5)
C39—C38—C28—C29	8.1 (3)	C21—C22—C27—C26	179.6 (3)
C37—C38—C28—C15	65.2 (4)	C10—C9—C14—C13	−0.7 (5)
C39—C38—C28—C15	−113.9 (2)	C8—C9—C14—C13	178.0 (3)
C20—C15—C28—N1	127.4 (2)	C11—C12—C13—C14	0.8 (6)
C16—C15—C28—N1	−114.5 (2)	C9—C14—C13—C12	0.5 (6)
C7—C15—C28—N1	7.5 (3)	C13—C12—C11—C10	−1.8 (6)
C20—C15—C28—C38	4.9 (3)	C9—C10—C11—C12	1.5 (5)
C16—C15—C28—C38	123.0 (2)	C30—C31—C32—C33	−0.6 (5)
C7—C15—C28—C38	−115.0 (2)	C24—C25—C26—C27	1.2 (6)
C20—C15—C28—C29	−111.2 (2)	Cl2—C25—C26—C27	179.8 (3)
C16—C15—C28—C29	6.9 (3)	C22—C27—C26—C25	0.4 (6)
C7—C15—C28—C29	128.9 (2)	C31—C32—C33—C34	0.4 (5)
C5—C6—C1—C2	−0.8 (4)	C35—C34—C33—C32	178.2 (3)
C7—C6—C1—C2	175.6 (2)	C39—C34—C33—C32	0.1 (5)
C25—C24—C23—C22	−0.1 (4)	C38—C37—C36—C35	−2.4 (5)
C27—C22—C23—C24	1.6 (4)	C37—C36—C35—C34	−0.4 (5)
C21—C22—C23—C24	−179.8 (3)	C39—C34—C35—C36	2.3 (5)
C28—N1—C8—C9	−162.0 (2)	C33—C34—C35—C36	−175.7 (3)
C28—N1—C8—C7	−40.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.41	2.789 (3)	102
C21—H21···O1	0.93	2.46	2.810 (4)	102
C27—H27···O1ⁱ	0.93	2.47	3.358 (4)	160
C16—H16A···O2ⁱⁱ	0.97	2.56	3.491 (3)	161
C32—H32···Cgⁱⁱⁱ	0.93	2.83	3.498 (5)	129

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

Experimental details

Crystal data
Chemical formula	C₃₉H₃₀Cl₂N₂O₂
M_r	629.55
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5567 (6), 12.0442 (11), 14.8593 (15)
α, β, γ (°)	76.025 (11), 75.445 (9), 76.220 (8)
V (Å³)	1577.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.24 × 0.15 × 0.14

Data collection
Diffractometer	Nonius MACH3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.947, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	6631, 5538, 3434
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.142, 1.02
No. of reflections	5538
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.29

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXTL/PC (Bruker, 2000), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.41	2.789 (3)	102
C21—H21···O1	0.93	2.46	2.810 (4)	102
C27—H27···O1ⁱ	0.93	2.47	3.358 (4)	160
C16—H16A···O2ⁱⁱ	0.97	2.56	3.491 (3)	161
C32—H32···Cgⁱⁱⁱ	0.93	2.83	3.498 (5)	129

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

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