5''-(4-Chloro-benzyl-idene)-1',1''-dimethyl-3'-phenyl-acenaphthene-1-spiro-2'-pyrrolidine-3'-spiro-3''-pyridine-2,4''-dione.

In the title compound, C(34)H(28)Cl(2)N(2)O(2), the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered piperidinone ring is in a distorted half-chair conformation. The mol-ecular structure shows three intra-molecular C-H⋯O inter-actions and the crystal packing is stabilized through inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological importance of pyrrolidines, 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 puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bonding inter­actions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C34H28Cl2N2O2

M = 567.48

Monoclinic,

a = 8.6561 (5) Å

b = 13.4732 (8) Å

c = 24.3962 (14) Å

β = 95.765 (12)°

V = 2830.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 (2) K

0.22 × 0.19 × 0.15 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.963, T max = 0.991

5802 measured reflections

4962 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.01

4962 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.38 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807059582/bt2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807059582/bt2624Isup2.hkl

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

C34H28Cl2N2O2	F000 = 1184
Mr = 567.48	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Melting point: 188 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 8.6561 (5) Å	Cell parameters from 25 reflections
b = 13.4732 (8) Å	θ = 10.5–13.6º
c = 24.3962 (14) Å	µ = 0.26 mm−1
β = 95.765 (12)º	T = 293 (2) K
V = 2830.8 (3) Å3	Block, yellow
Z = 4	0.22 × 0.19 × 0.15 mm

Nonius MACH3 sealed-tube diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.3º
T = 293(2) K	h = 0→10
ω/2θ scans	k = −1→16
Absorption correction: ψ scan(North et al., 1968)	l = −28→28
Tmin = 0.963, Tmax = 0.991	3 standard reflections
5802 measured reflections	every 60 min
4962 independent reflections	intensity decay: none
3252 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.054P)2 + 1.3189P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4962 reflections	Δρmax = 0.23 e Å−3
361 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Cl2	0.79695 (10)	0.00677 (7)	1.03985 (4)	0.0837 (3)
Cl1	0.16195 (12)	−0.09337 (8)	0.47557 (3)	0.0930 (3)
O1	0.59114 (19)	0.19348 (15)	0.77239 (7)	0.0545 (5)
O2	0.01134 (19)	0.30256 (13)	0.83128 (7)	0.0489 (4)
N1	0.1503 (2)	0.11928 (13)	0.79730 (7)	0.0337 (4)
N2	0.3200 (2)	0.40244 (14)	0.83147 (8)	0.0401 (5)
C11	0.3686 (2)	0.22873 (16)	0.82027 (8)	0.0319 (5)
C12	0.4534 (3)	0.17972 (17)	0.77550 (9)	0.0359 (5)
C23	0.2670 (2)	0.32052 (16)	0.79520 (9)	0.0335 (5)
C34	0.1497 (3)	0.31854 (16)	0.70216 (9)	0.0377 (5)
C14	0.4792 (3)	0.27742 (17)	0.86653 (9)	0.0355 (5)
H14	0.5639	0.3075	0.8485	0.043*
C15	0.5539 (3)	0.20976 (17)	0.91073 (9)	0.0381 (5)
C33	0.2867 (3)	0.34333 (16)	0.73527 (9)	0.0363 (5)
C10	0.2658 (3)	0.14841 (17)	0.84174 (9)	0.0347 (5)
H10A	0.3283	0.0915	0.8543	0.042*
H10B	0.2150	0.1737	0.8726	0.042*
C9	0.2157 (3)	0.06607 (18)	0.75306 (9)	0.0397 (5)
H9A	0.1378	0.0615	0.7217	0.048*
H9B	0.2418	−0.0009	0.7653	0.048*
C8	0.3586 (3)	0.11524 (16)	0.73517 (8)	0.0347 (5)
C6	0.3385 (3)	0.05882 (18)	0.63499 (9)	0.0404 (6)
C32	0.4090 (3)	0.3797 (2)	0.71080 (10)	0.0494 (6)
H32	0.4994	0.3992	0.7318	0.059*
C25	0.0276 (3)	0.29142 (17)	0.73259 (9)	0.0393 (5)
C28	−0.0111 (4)	0.2950 (2)	0.61790 (11)	0.0602 (8)
H28	−0.0268	0.2946	0.5796	0.072*
C21	0.3811 (3)	0.36211 (18)	0.88423 (9)	0.0417 (6)
H21A	0.2987	0.3386	0.9051	0.050*
H21B	0.4434	0.4106	0.9060	0.050*
C7	0.4055 (3)	0.10997 (18)	0.68459 (9)	0.0403 (5)
H7	0.4962	0.1448	0.6803	0.048*
C1	0.2430 (3)	−0.02498 (18)	0.63447 (10)	0.0433 (6)
H1	0.2161	−0.0503	0.6677	0.052*
C24	0.0865 (3)	0.29821 (17)	0.79197 (10)	0.0383 (5)
C2	0.1876 (3)	−0.0710 (2)	0.58587 (10)	0.0495 (6)
H2	0.1237	−0.1264	0.5863	0.059*
C30	0.2659 (4)	0.3587 (2)	0.62012 (11)	0.0594 (7)
H30	0.2638	0.3622	0.5820	0.071*
C20	0.4931 (3)	0.1922 (2)	0.95991 (10)	0.0581 (7)
H20	0.4002	0.2223	0.9666	0.070*
C5	0.3761 (3)	0.0938 (2)	0.58421 (10)	0.0542 (7)
H5	0.4396	0.1493	0.5832	0.065*
C4	0.3216 (4)	0.0480 (2)	0.53541 (10)	0.0632 (8)
H4	0.3479	0.0726	0.5020	0.076*
C27	−0.1289 (4)	0.2677 (2)	0.64769 (12)	0.0646 (8)
H27	−0.2232	0.2490	0.6289	0.078*
C26	−0.1144 (3)	0.2666 (2)	0.70582 (12)	0.0541 (7)
H26	−0.1977	0.2497	0.7252	0.065*
C13	0.0192 (3)	0.0667 (2)	0.81641 (10)	0.0503 (6)
H13A	−0.0529	0.0493	0.7854	0.075*
H13B	−0.0314	0.1086	0.8409	0.075*
H13C	0.0554	0.0075	0.8355	0.075*
C18	0.7050 (3)	0.0867 (2)	0.99047 (11)	0.0529 (7)
C3	0.2282 (3)	−0.0340 (2)	0.53678 (10)	0.0556 (7)
C16	0.6941 (3)	0.1650 (2)	0.90364 (11)	0.0581 (7)
H16	0.7397	0.1770	0.8713	0.070*
C17	0.7690 (3)	0.1030 (2)	0.94300 (11)	0.0635 (8)
H17	0.8623	0.0728	0.9368	0.076*
C19	0.5681 (4)	0.1303 (3)	0.99969 (11)	0.0674 (9)
H19	0.5248	0.1187	1.0325	0.081*
C29	0.1345 (3)	0.32391 (18)	0.64422 (10)	0.0474 (6)
C22	0.2206 (3)	0.48950 (19)	0.83214 (12)	0.0555 (7)
H22A	0.1872	0.5091	0.7950	0.083*
H22B	0.2775	0.5429	0.8508	0.083*
H22C	0.1316	0.4740	0.8511	0.083*
C31	0.3962 (4)	0.3872 (2)	0.65256 (11)	0.0622 (8)
H31	0.4796	0.4126	0.6358	0.075*

	U11	U22	U33	U12	U13	U23
Cl2	0.0812 (6)	0.0873 (6)	0.0762 (5)	−0.0048 (5)	−0.0242 (4)	0.0362 (5)
Cl1	0.1263 (8)	0.1056 (7)	0.0430 (4)	−0.0021 (6)	−0.0113 (4)	−0.0216 (4)
O1	0.0353 (10)	0.0801 (13)	0.0498 (10)	−0.0078 (9)	0.0125 (8)	−0.0128 (9)
O2	0.0444 (9)	0.0534 (11)	0.0518 (10)	0.0026 (8)	0.0182 (8)	−0.0063 (8)
N1	0.0334 (10)	0.0378 (10)	0.0308 (9)	−0.0055 (8)	0.0082 (8)	−0.0027 (8)
N2	0.0466 (11)	0.0340 (10)	0.0388 (10)	0.0000 (9)	−0.0001 (9)	−0.0031 (8)
C11	0.0319 (11)	0.0348 (12)	0.0294 (11)	−0.0015 (9)	0.0054 (9)	−0.0003 (9)
C12	0.0343 (13)	0.0387 (13)	0.0356 (12)	−0.0006 (10)	0.0079 (10)	0.0025 (10)
C23	0.0321 (11)	0.0345 (12)	0.0342 (11)	−0.0031 (10)	0.0043 (9)	−0.0030 (9)
C34	0.0417 (13)	0.0314 (12)	0.0396 (12)	0.0022 (10)	0.0025 (10)	0.0010 (10)
C14	0.0334 (11)	0.0405 (13)	0.0325 (11)	−0.0049 (10)	0.0032 (9)	−0.0018 (10)
C15	0.0361 (13)	0.0419 (13)	0.0355 (12)	−0.0056 (11)	0.0003 (10)	−0.0029 (10)
C33	0.0395 (13)	0.0322 (12)	0.0374 (12)	−0.0018 (10)	0.0044 (10)	0.0021 (9)
C10	0.0369 (12)	0.0361 (12)	0.0317 (11)	−0.0014 (10)	0.0069 (9)	0.0006 (9)
C9	0.0399 (12)	0.0415 (13)	0.0381 (12)	−0.0048 (11)	0.0057 (10)	−0.0084 (10)
C8	0.0353 (12)	0.0364 (12)	0.0330 (11)	0.0057 (10)	0.0069 (9)	−0.0020 (10)
C6	0.0455 (13)	0.0423 (13)	0.0344 (12)	0.0088 (12)	0.0087 (10)	−0.0021 (10)
C32	0.0511 (15)	0.0525 (16)	0.0451 (14)	−0.0128 (13)	0.0083 (12)	0.0064 (12)
C25	0.0360 (12)	0.0378 (13)	0.0430 (13)	0.0032 (11)	−0.0012 (10)	0.0001 (10)
C28	0.079 (2)	0.0536 (17)	0.0435 (15)	−0.0013 (15)	−0.0166 (14)	−0.0021 (13)
C21	0.0456 (14)	0.0420 (13)	0.0370 (12)	−0.0065 (11)	0.0028 (10)	−0.0056 (10)
C7	0.0404 (13)	0.0424 (13)	0.0394 (13)	0.0009 (11)	0.0106 (10)	−0.0025 (11)
C1	0.0490 (14)	0.0457 (14)	0.0364 (12)	0.0062 (12)	0.0097 (11)	−0.0025 (11)
C24	0.0366 (12)	0.0349 (13)	0.0444 (13)	0.0022 (10)	0.0089 (11)	−0.0009 (10)
C2	0.0529 (15)	0.0507 (15)	0.0447 (14)	0.0044 (13)	0.0046 (12)	−0.0083 (12)
C30	0.084 (2)	0.0600 (17)	0.0349 (14)	−0.0036 (16)	0.0117 (14)	0.0073 (13)
C20	0.0528 (16)	0.078 (2)	0.0446 (15)	0.0064 (15)	0.0097 (12)	0.0115 (14)
C5	0.0750 (19)	0.0486 (15)	0.0409 (14)	−0.0019 (14)	0.0147 (13)	0.0030 (12)
C4	0.097 (2)	0.0628 (19)	0.0303 (13)	0.0078 (18)	0.0092 (14)	0.0061 (13)
C27	0.0573 (18)	0.0663 (19)	0.0642 (18)	−0.0066 (15)	−0.0237 (15)	−0.0011 (15)
C26	0.0410 (14)	0.0542 (17)	0.0654 (18)	−0.0037 (13)	−0.0036 (12)	0.0035 (14)
C13	0.0458 (14)	0.0588 (16)	0.0479 (14)	−0.0162 (13)	0.0131 (12)	−0.0055 (13)
C18	0.0520 (16)	0.0557 (17)	0.0472 (15)	−0.0054 (13)	−0.0130 (12)	0.0098 (13)
C3	0.0690 (18)	0.0595 (18)	0.0367 (14)	0.0136 (15)	−0.0026 (12)	−0.0080 (12)
C16	0.0562 (17)	0.075 (2)	0.0441 (15)	0.0151 (15)	0.0114 (13)	0.0113 (14)
C17	0.0539 (16)	0.080 (2)	0.0558 (17)	0.0180 (15)	0.0009 (13)	0.0116 (15)
C19	0.0661 (19)	0.096 (2)	0.0403 (15)	−0.0029 (18)	0.0058 (13)	0.0192 (16)
C29	0.0653 (17)	0.0386 (14)	0.0369 (13)	0.0038 (12)	−0.0014 (12)	0.0014 (11)
C22	0.0649 (17)	0.0398 (14)	0.0602 (17)	0.0069 (13)	−0.0015 (14)	−0.0080 (12)
C31	0.075 (2)	0.0643 (19)	0.0504 (16)	−0.0144 (16)	0.0210 (15)	0.0113 (14)

Cl2—C18	1.747 (3)	C25—C26	1.374 (3)
Cl1—C3	1.740 (3)	C25—C24	1.489 (3)
O1—C12	1.217 (3)	C28—C27	1.361 (4)
O2—C24	1.213 (3)	C28—C29	1.411 (4)
N1—C10	1.453 (3)	C28—H28	0.9300
N1—C13	1.454 (3)	C21—H21A	0.9700
N1—C9	1.457 (3)	C21—H21B	0.9700
N2—C21	1.447 (3)	C7—H7	0.9300
N2—C22	1.456 (3)	C1—C2	1.381 (3)
N2—C23	1.459 (3)	C1—H1	0.9300
C11—C12	1.526 (3)	C2—C3	1.376 (4)
C11—C10	1.527 (3)	C2—H2	0.9300
C11—C14	1.550 (3)	C30—C31	1.366 (4)
C11—C23	1.603 (3)	C30—C29	1.412 (4)
C12—C8	1.495 (3)	C30—H30	0.9300
C23—C33	1.520 (3)	C20—C19	1.390 (4)
C23—C24	1.586 (3)	C20—H20	0.9300
C34—C25	1.399 (3)	C5—C4	1.381 (4)
C34—C33	1.407 (3)	C5—H5	0.9300
C34—C29	1.408 (3)	C4—C3	1.371 (4)
C14—C15	1.507 (3)	C4—H4	0.9300
C14—C21	1.511 (3)	C27—C26	1.411 (4)
C14—H14	0.9800	C27—H27	0.9300
C15—C20	1.378 (3)	C26—H26	0.9300
C15—C16	1.381 (3)	C13—H13A	0.9600
C33—C32	1.358 (3)	C13—H13B	0.9600
C10—H10A	0.9700	C13—H13C	0.9600
C10—H10B	0.9700	C18—C17	1.351 (4)
C9—C8	1.506 (3)	C18—C19	1.361 (4)
C9—H9A	0.9700	C16—C17	1.384 (4)
C9—H9B	0.9700	C16—H16	0.9300
C8—C7	1.339 (3)	C17—H17	0.9300
C6—C5	1.394 (3)	C19—H19	0.9300
C6—C1	1.399 (3)	C22—H22A	0.9600
C6—C7	1.461 (3)	C22—H22B	0.9600
C32—C31	1.418 (4)	C22—H22C	0.9600
C32—H32	0.9300	C31—H31	0.9300
C10—N1—C13	113.15 (17)	N2—C21—H21B	111.5
C10—N1—C9	113.37 (17)	C14—C21—H21B	111.5
C13—N1—C9	111.81 (18)	H21A—C21—H21B	109.3
C21—N2—C22	117.14 (19)	C8—C7—C6	131.0 (2)
C21—N2—C23	108.65 (18)	C8—C7—H7	114.5
C22—N2—C23	117.80 (18)	C6—C7—H7	114.5
C12—C11—C10	106.12 (17)	C2—C1—C6	121.6 (2)
C12—C11—C14	113.47 (18)	C2—C1—H1	119.2
C10—C11—C14	112.87 (17)	C6—C1—H1	119.2
C12—C11—C23	110.21 (16)	O2—C24—C25	127.9 (2)
C10—C11—C23	111.17 (17)	O2—C24—C23	123.8 (2)
C14—C11—C23	103.08 (17)	C25—C24—C23	107.40 (18)
O1—C12—C8	121.6 (2)	C3—C2—C1	119.2 (3)
O1—C12—C11	121.6 (2)	C3—C2—H2	120.4
C8—C12—C11	116.82 (18)	C1—C2—H2	120.4
N2—C23—C33	111.81 (18)	C31—C30—C29	120.3 (2)
N2—C23—C24	114.92 (18)	C31—C30—H30	119.8
C33—C23—C24	101.28 (17)	C29—C30—H30	119.8
N2—C23—C11	103.02 (16)	C15—C20—C19	121.3 (3)
C33—C23—C11	114.38 (17)	C15—C20—H20	119.4
C24—C23—C11	111.90 (17)	C19—C20—H20	119.4
C25—C34—C33	113.3 (2)	C4—C5—C6	121.7 (3)
C25—C34—C29	123.1 (2)	C4—C5—H5	119.2
C33—C34—C29	123.5 (2)	C6—C5—H5	119.2
C15—C14—C21	117.74 (18)	C3—C4—C5	119.3 (2)
C15—C14—C11	117.01 (19)	C3—C4—H4	120.3
C21—C14—C11	101.79 (18)	C5—C4—H4	120.3
C15—C14—H14	106.5	C28—C27—C26	122.9 (3)
C21—C14—H14	106.5	C28—C27—H27	118.5
C11—C14—H14	106.5	C26—C27—H27	118.5
C20—C15—C16	116.8 (2)	C25—C26—C27	117.4 (3)
C20—C15—C14	123.6 (2)	C25—C26—H26	121.3
C16—C15—C14	119.6 (2)	C27—C26—H26	121.3
C32—C33—C34	118.9 (2)	N1—C13—H13A	109.5
C32—C33—C23	131.5 (2)	N1—C13—H13B	109.5
C34—C33—C23	109.56 (19)	H13A—C13—H13B	109.5
N1—C10—C11	108.45 (17)	N1—C13—H13C	109.5
N1—C10—H10A	110.0	H13A—C13—H13C	109.5
C11—C10—H10A	110.0	H13B—C13—H13C	109.5
N1—C10—H10B	110.0	C17—C18—C19	120.7 (2)
C11—C10—H10B	110.0	C17—C18—Cl2	119.5 (2)
H10A—C10—H10B	108.4	C19—C18—Cl2	119.7 (2)
N1—C9—C8	112.94 (18)	C4—C3—C2	121.1 (2)
N1—C9—H9A	109.0	C4—C3—Cl1	119.6 (2)
C8—C9—H9A	109.0	C2—C3—Cl1	119.3 (2)
N1—C9—H9B	109.0	C15—C16—C17	122.2 (2)
C8—C9—H9B	109.0	C15—C16—H16	118.9
H9A—C9—H9B	107.8	C17—C16—H16	118.9
C7—C8—C12	116.1 (2)	C18—C17—C16	119.2 (3)
C7—C8—C9	125.3 (2)	C18—C17—H17	120.4
C12—C8—C9	118.53 (18)	C16—C17—H17	120.4
C5—C6—C1	117.1 (2)	C18—C19—C20	119.8 (3)
C5—C6—C7	117.9 (2)	C18—C19—H19	120.1
C1—C6—C7	125.0 (2)	C20—C19—H19	120.1
C33—C32—C31	118.7 (2)	C34—C29—C28	115.6 (2)
C33—C32—H32	120.6	C34—C29—C30	115.9 (2)
C31—C32—H32	120.6	C28—C29—C30	128.5 (2)
C26—C25—C34	119.9 (2)	N2—C22—H22A	109.5
C26—C25—C24	132.8 (2)	N2—C22—H22B	109.5
C34—C25—C24	107.30 (19)	H22A—C22—H22B	109.5
C27—C28—C29	121.0 (3)	N2—C22—H22C	109.5
C27—C28—H28	119.5	H22A—C22—H22C	109.5
C29—C28—H28	119.5	H22B—C22—H22C	109.5
N2—C21—C14	101.25 (18)	C30—C31—C32	122.5 (3)
N2—C21—H21A	111.5	C30—C31—H31	118.7
C14—C21—H21A	111.5	C32—C31—H31	118.7
C10—C11—C12—O1	−136.4 (2)	C33—C34—C25—C26	179.1 (2)
C14—C11—C12—O1	−11.9 (3)	C29—C34—C25—C26	1.3 (4)
C23—C11—C12—O1	103.1 (2)	C33—C34—C25—C24	0.0 (3)
C10—C11—C12—C8	44.5 (2)	C29—C34—C25—C24	−177.8 (2)
C14—C11—C12—C8	168.98 (18)	C22—N2—C21—C14	−178.3 (2)
C23—C11—C12—C8	−76.0 (2)	C23—N2—C21—C14	45.1 (2)
C21—N2—C23—C33	−148.01 (19)	C15—C14—C21—N2	−174.89 (19)
C22—N2—C23—C33	75.8 (3)	C11—C14—C21—N2	−45.6 (2)
C21—N2—C23—C24	97.3 (2)	C12—C8—C7—C6	−177.0 (2)
C22—N2—C23—C24	−39.0 (3)	C9—C8—C7—C6	−0.2 (4)
C21—N2—C23—C11	−24.7 (2)	C5—C6—C7—C8	156.9 (3)
C22—N2—C23—C11	−160.95 (19)	C1—C6—C7—C8	−25.3 (4)
C12—C11—C23—N2	−126.14 (18)	C5—C6—C1—C2	−0.3 (4)
C10—C11—C23—N2	116.48 (18)	C7—C6—C1—C2	−178.1 (2)
C14—C11—C23—N2	−4.7 (2)	C26—C25—C24—O2	−16.8 (4)
C12—C11—C23—C33	−4.6 (2)	C34—C25—C24—O2	162.2 (2)
C10—C11—C23—C33	−121.96 (19)	C26—C25—C24—C23	174.4 (3)
C14—C11—C23—C33	116.85 (19)	C34—C25—C24—C23	−6.7 (2)
C12—C11—C23—C24	109.9 (2)	N2—C23—C24—O2	−38.6 (3)
C10—C11—C23—C24	−7.5 (2)	C33—C23—C24—O2	−159.3 (2)
C14—C11—C23—C24	−128.71 (18)	C11—C23—C24—O2	78.5 (3)
C12—C11—C14—C15	−80.6 (2)	N2—C23—C24—C25	130.85 (19)
C10—C11—C14—C15	40.2 (3)	C33—C23—C24—C25	10.2 (2)
C23—C11—C14—C15	160.19 (18)	C11—C23—C24—C25	−112.1 (2)
C12—C11—C14—C21	149.59 (19)	C6—C1—C2—C3	0.4 (4)
C10—C11—C14—C21	−89.6 (2)	C16—C15—C20—C19	−1.6 (4)
C23—C11—C14—C21	30.4 (2)	C14—C15—C20—C19	−179.0 (3)
C21—C14—C15—C20	28.1 (3)	C1—C6—C5—C4	0.1 (4)
C11—C14—C15—C20	−93.8 (3)	C7—C6—C5—C4	178.1 (3)
C21—C14—C15—C16	−149.2 (2)	C6—C5—C4—C3	−0.1 (4)
C11—C14—C15—C16	89.0 (3)	C29—C28—C27—C26	0.1 (5)
C25—C34—C33—C32	−174.0 (2)	C34—C25—C26—C27	1.4 (4)
C29—C34—C33—C32	3.8 (4)	C24—C25—C26—C27	−179.8 (3)
C25—C34—C33—C23	7.1 (3)	C28—C27—C26—C25	−2.1 (4)
C29—C34—C33—C23	−175.1 (2)	C5—C4—C3—C2	0.3 (4)
N2—C23—C33—C32	48.1 (3)	C5—C4—C3—Cl1	−178.8 (2)
C24—C23—C33—C32	171.0 (3)	C1—C2—C3—C4	−0.4 (4)
C11—C23—C33—C32	−68.5 (3)	C1—C2—C3—Cl1	178.66 (19)
N2—C23—C33—C34	−133.19 (19)	C20—C15—C16—C17	1.9 (4)
C24—C23—C33—C34	−10.3 (2)	C14—C15—C16—C17	179.4 (3)
C11—C23—C33—C34	110.2 (2)	C19—C18—C17—C16	0.3 (5)
C13—N1—C10—C11	−162.47 (19)	Cl2—C18—C17—C16	178.8 (2)
C9—N1—C10—C11	68.8 (2)	C15—C16—C17—C18	−1.3 (5)
C12—C11—C10—N1	−64.3 (2)	C17—C18—C19—C20	0.0 (5)
C14—C11—C10—N1	170.79 (17)	Cl2—C18—C19—C20	−178.6 (2)
C23—C11—C10—N1	55.5 (2)	C15—C20—C19—C18	0.7 (5)
C10—N1—C9—C8	−46.6 (3)	C25—C34—C29—C28	−3.1 (4)
C13—N1—C9—C8	−175.97 (19)	C33—C34—C29—C28	179.3 (2)
O1—C12—C8—C7	−28.8 (3)	C25—C34—C29—C30	176.0 (2)
C11—C12—C8—C7	150.3 (2)	C33—C34—C29—C30	−1.5 (4)
O1—C12—C8—C9	154.2 (2)	C27—C28—C29—C34	2.4 (4)
C11—C12—C8—C9	−26.7 (3)	C27—C28—C29—C30	−176.6 (3)
N1—C9—C8—C7	−151.4 (2)	C31—C30—C29—C34	−1.7 (4)
N1—C9—C8—C12	25.3 (3)	C31—C30—C29—C28	177.4 (3)
C34—C33—C32—C31	−2.7 (4)	C29—C30—C31—C32	2.7 (5)
C23—C33—C32—C31	175.9 (2)	C33—C32—C31—C30	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.40	2.783 (3)	104
C14—H14···O1	0.98	2.44	2.818 (3)	102
C22—H22C···O2	0.96	2.56	3.101 (3)	116
C26—H26···O1i	0.93	2.38	3.307 (3)	176
C21—H21B···Cg1ii	0.97	2.73	3.559 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.93	2.40	2.783 (3)	104
C14—H14⋯O1	0.98	2.44	2.818 (3)	102
C22—H22C⋯O2	0.96	2.56	3.101 (3)	116
C26—H26⋯O1i	0.93	2.38	3.307 (3)	176
C21—H21B⋯Cg1ii	0.97	2.73	3.559 (3)	144

Symmetry codes: (i) ; (ii) .