4'-Methyl-14',19'-dioxa-4'-aza-spiro-[acenaphthyl-ene-1,5'-tetra-cyclo-[18.4.0.0(2,6).0(8,13)]tetra-cosa-ne]-1'(24'),8',10',12',20',22'-hexa-ene-2,7'(1H)-dione.

In the title compound, C33H29NO4, the acenaphthyl-ene ring system is essentially planar (r.m.s. deviation = 0.0290 Å). The pyrrolidine ring adopts a C-envelope conformation with a C atom displaced by 0.671 (2) Å from the mean-plane formed by the remaining ring atoms. The pyrrolidine ring is fused to acenaphthyl-ene ring system making a dihedral angle of 88.0 (7)°. In the crystal, mol-ecules are linked into R(2)2(9) dimers via C-H⋯N and C-H⋯O hydrogen bonds. Two C atoms act as donors to the same O atom acceptor, resulting in the formation of R(2)1(7) ring motifs. These two motifs combine to form hydrogen-bonded sheets running along the a- and b-axis directions.

Related literature

For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995 ▶). For related structures, see: Augustine et al. (2010 ▶); Narayanan et al. (2012 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C33H29NO4

M = 503.57

Monoclinic,

a = 11.248 (2) Å

b = 16.609 (3) Å

c = 14.037 (3) Å

β = 92.965 (6)°

V = 2618.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.979, T max = 0.984

24740 measured reflections

6363 independent reflections

4183 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.01

6363 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046144/pv2602sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046144/pv2602Isup2.hkl

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

C33H29NO4	F(000) = 1064
Mr = 503.57	Dx = 1.277 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6363 reflections
a = 11.248 (2) Å	θ = 1.8–28.3°
b = 16.609 (3) Å	µ = 0.08 mm−1
c = 14.037 (3) Å	T = 293 K
β = 92.965 (6)°	Block, colorless
V = 2618.8 (9) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6363 independent reflections
Radiation source: fine-focus sealed tube	4183 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.979, Tmax = 0.984	k = −21→19
24740 measured reflections	l = −18→18

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.572P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
6363 reflections	Δρmax = 0.22 e Å−3
345 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0125 (10)

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
C1	0.23872 (16)	0.09798 (10)	0.09848 (11)	0.0548 (4)
H1A	0.2555	0.1542	0.0861	0.066*
H1B	0.2240	0.0706	0.0380	0.066*
C2	0.34391 (14)	0.05856 (9)	0.15621 (10)	0.0447 (4)
H2	0.3567	0.0056	0.1276	0.054*
C3	0.29234 (12)	0.04354 (8)	0.25405 (9)	0.0358 (3)
H3	0.2970	0.0936	0.2911	0.043*
C4	0.16007 (13)	0.02549 (8)	0.22597 (10)	0.0407 (3)
C5	0.08158 (14)	0.03292 (9)	0.31428 (12)	0.0487 (4)
C6	0.02699 (14)	−0.04693 (10)	0.32978 (14)	0.0580 (5)
C7	−0.04217 (18)	−0.07611 (14)	0.39953 (19)	0.0829 (7)
H7	−0.0639	−0.0439	0.4499	0.100*
C8	−0.0792 (2)	−0.15770 (18)	0.3916 (3)	0.1069 (10)
H8	−0.1244	−0.1792	0.4391	0.128*
C9	−0.0513 (2)	−0.20604 (16)	0.3171 (3)	0.1046 (10)
H9	−0.0800	−0.2585	0.3142	0.126*
C10	0.02022 (18)	−0.17780 (11)	0.24486 (19)	0.0766 (6)
C11	0.05975 (15)	−0.09741 (10)	0.25487 (14)	0.0569 (5)
C12	0.13465 (14)	−0.06061 (9)	0.19125 (12)	0.0488 (4)
C13	0.16914 (19)	−0.10407 (10)	0.11489 (14)	0.0652 (5)
H13	0.2189	−0.0812	0.0714	0.078*
C14	0.1285 (2)	−0.18403 (12)	0.10263 (18)	0.0841 (7)
H14	0.1515	−0.2128	0.0498	0.101*
C15	0.0580 (2)	−0.22028 (12)	0.1642 (2)	0.0908 (8)
H15	0.0340	−0.2733	0.1538	0.109*
C16	0.02011 (19)	0.08788 (12)	0.10598 (16)	0.0748 (6)
H16A	0.0151	0.0405	0.0667	0.112*
H16B	0.0105	0.1349	0.0665	0.112*
H16C	−0.0415	0.0865	0.1508	0.112*
C17	0.35059 (13)	−0.02308 (8)	0.31245 (10)	0.0392 (3)
C18	0.33202 (13)	−0.02667 (8)	0.41733 (10)	0.0402 (3)
C19	0.29524 (16)	−0.09961 (10)	0.45511 (13)	0.0562 (4)
H19	0.2801	−0.1431	0.4146	0.067*
C20	0.28089 (18)	−0.10834 (12)	0.55164 (15)	0.0695 (5)
H20	0.2542	−0.1569	0.5757	0.083*
C21	0.30611 (18)	−0.04520 (13)	0.61134 (13)	0.0671 (5)
H21	0.2985	−0.0515	0.6766	0.081*
C22	0.34253 (16)	0.02753 (11)	0.57657 (12)	0.0561 (4)
H22	0.3598	0.0699	0.6183	0.067*
C23	0.35360 (13)	0.03799 (9)	0.47915 (10)	0.0413 (3)
C24	0.41564 (17)	0.17608 (10)	0.50022 (12)	0.0553 (4)
H24A	0.4800	0.1637	0.5465	0.066*
H24B	0.3459	0.1909	0.5341	0.066*
C25	0.45091 (18)	0.24358 (11)	0.43577 (13)	0.0621 (5)
H25A	0.5106	0.2239	0.3941	0.075*
H25B	0.4868	0.2863	0.4745	0.075*
C26	0.34744 (18)	0.27817 (11)	0.37493 (13)	0.0642 (5)
H26A	0.2802	0.2419	0.3776	0.077*
H26B	0.3244	0.3291	0.4023	0.077*
C27	0.37315 (18)	0.29175 (9)	0.27161 (13)	0.0589 (5)
H27A	0.3124	0.3262	0.2417	0.071*
H27B	0.4495	0.3184	0.2676	0.071*
C28	0.47683 (15)	0.18063 (9)	0.19420 (11)	0.0476 (4)
C29	0.58811 (16)	0.21697 (11)	0.19675 (13)	0.0592 (5)
H29	0.5977	0.2688	0.2210	0.071*
C30	0.68444 (17)	0.17641 (13)	0.16345 (14)	0.0694 (5)
H30	0.7587	0.2011	0.1655	0.083*
C31	0.67185 (18)	0.10011 (14)	0.12739 (14)	0.0694 (5)
H31	0.7370	0.0731	0.1046	0.083*
C32	0.56117 (17)	0.06348 (12)	0.12523 (12)	0.0591 (5)
H32	0.5531	0.0116	0.1009	0.071*
C33	0.46186 (15)	0.10206 (10)	0.15840 (10)	0.0468 (4)
N1	0.13583 (12)	0.09043 (7)	0.15743 (9)	0.0472 (3)
O1	0.07071 (12)	0.09415 (7)	0.35944 (9)	0.0664 (4)
O2	0.40539 (11)	−0.07668 (7)	0.27515 (8)	0.0599 (3)
O3	0.39011 (10)	0.10797 (6)	0.43954 (7)	0.0497 (3)
O4	0.37498 (10)	0.21578 (7)	0.22268 (8)	0.0569 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0767 (12)	0.0497 (9)	0.0371 (8)	0.0005 (8)	−0.0065 (8)	0.0038 (7)
C2	0.0589 (10)	0.0389 (8)	0.0367 (7)	0.0005 (7)	0.0053 (7)	−0.0021 (6)
C3	0.0430 (8)	0.0286 (7)	0.0356 (7)	−0.0007 (5)	0.0004 (6)	−0.0025 (5)
C4	0.0445 (8)	0.0300 (7)	0.0467 (8)	0.0009 (6)	−0.0044 (6)	−0.0016 (6)
C5	0.0404 (8)	0.0408 (8)	0.0647 (10)	0.0051 (6)	0.0028 (7)	0.0039 (8)
C6	0.0360 (8)	0.0512 (10)	0.0865 (13)	−0.0024 (7)	−0.0001 (8)	0.0147 (9)
C7	0.0502 (11)	0.0831 (15)	0.1170 (18)	−0.0046 (10)	0.0184 (11)	0.0275 (13)
C8	0.0591 (14)	0.0902 (19)	0.172 (3)	−0.0192 (13)	0.0140 (16)	0.057 (2)
C9	0.0675 (15)	0.0611 (15)	0.183 (3)	−0.0210 (12)	−0.0202 (17)	0.0360 (17)
C10	0.0598 (12)	0.0417 (10)	0.1246 (19)	−0.0126 (9)	−0.0300 (12)	0.0176 (12)
C11	0.0439 (9)	0.0383 (9)	0.0863 (13)	−0.0032 (7)	−0.0180 (9)	0.0071 (8)
C12	0.0512 (9)	0.0337 (8)	0.0596 (10)	−0.0002 (7)	−0.0158 (7)	−0.0022 (7)
C13	0.0867 (14)	0.0409 (9)	0.0656 (11)	0.0041 (9)	−0.0182 (10)	−0.0117 (8)
C14	0.1166 (19)	0.0401 (11)	0.0908 (15)	0.0066 (11)	−0.0411 (14)	−0.0164 (11)
C15	0.1038 (18)	0.0339 (10)	0.128 (2)	−0.0062 (11)	−0.0552 (16)	−0.0039 (13)
C16	0.0739 (13)	0.0638 (12)	0.0828 (14)	0.0077 (10)	−0.0346 (11)	−0.0002 (10)
C17	0.0404 (8)	0.0318 (7)	0.0451 (8)	−0.0005 (6)	−0.0007 (6)	−0.0023 (6)
C18	0.0384 (8)	0.0376 (8)	0.0442 (8)	0.0039 (6)	−0.0023 (6)	0.0070 (6)
C19	0.0613 (11)	0.0435 (9)	0.0634 (11)	−0.0025 (8)	−0.0003 (8)	0.0111 (8)
C20	0.0752 (13)	0.0629 (12)	0.0709 (13)	−0.0046 (10)	0.0097 (10)	0.0294 (10)
C21	0.0765 (13)	0.0773 (13)	0.0482 (10)	0.0074 (10)	0.0096 (9)	0.0210 (10)
C22	0.0633 (11)	0.0628 (11)	0.0420 (9)	0.0085 (8)	0.0010 (8)	0.0034 (8)
C23	0.0405 (8)	0.0422 (8)	0.0410 (8)	0.0047 (6)	−0.0005 (6)	0.0050 (6)
C24	0.0724 (11)	0.0472 (9)	0.0457 (9)	−0.0012 (8)	−0.0037 (8)	−0.0094 (7)
C25	0.0727 (12)	0.0509 (10)	0.0621 (11)	−0.0082 (9)	−0.0020 (9)	−0.0078 (8)
C26	0.0783 (13)	0.0507 (10)	0.0644 (11)	0.0104 (9)	0.0099 (10)	−0.0038 (8)
C27	0.0776 (12)	0.0345 (8)	0.0648 (11)	−0.0015 (8)	0.0075 (9)	0.0031 (8)
C28	0.0563 (10)	0.0461 (9)	0.0410 (8)	−0.0045 (7)	0.0083 (7)	0.0086 (7)
C29	0.0634 (11)	0.0561 (10)	0.0585 (10)	−0.0112 (9)	0.0089 (8)	0.0099 (8)
C30	0.0549 (11)	0.0847 (15)	0.0694 (12)	−0.0108 (10)	0.0103 (9)	0.0195 (11)
C31	0.0581 (12)	0.0888 (15)	0.0631 (11)	0.0089 (10)	0.0203 (9)	0.0109 (11)
C32	0.0668 (12)	0.0640 (11)	0.0477 (9)	0.0056 (9)	0.0145 (8)	0.0003 (8)
C33	0.0557 (9)	0.0500 (9)	0.0356 (7)	−0.0009 (7)	0.0103 (7)	0.0051 (6)
N1	0.0544 (8)	0.0381 (7)	0.0474 (7)	0.0035 (6)	−0.0124 (6)	0.0029 (5)
O1	0.0762 (9)	0.0486 (7)	0.0767 (8)	0.0104 (6)	0.0253 (7)	−0.0038 (6)
O2	0.0757 (8)	0.0466 (7)	0.0571 (7)	0.0223 (6)	0.0017 (6)	−0.0050 (5)
O3	0.0681 (7)	0.0412 (6)	0.0393 (5)	−0.0081 (5)	−0.0009 (5)	−0.0042 (4)
O4	0.0603 (7)	0.0441 (6)	0.0676 (7)	−0.0071 (5)	0.0152 (6)	−0.0077 (5)

C1—N1	1.462 (2)	C17—C18	1.499 (2)
C1—C2	1.545 (2)	C18—C19	1.394 (2)
C1—H1A	0.9700	C18—C23	1.394 (2)
C1—H1B	0.9700	C19—C20	1.381 (3)
C2—C33	1.510 (2)	C19—H19	0.9300
C2—C3	1.5386 (19)	C20—C21	1.363 (3)
C2—H2	0.9800	C20—H20	0.9300
C3—C17	1.5067 (19)	C21—C22	1.373 (3)
C3—C4	1.548 (2)	C21—H21	0.9300
C3—H3	0.9800	C22—C23	1.390 (2)
C4—N1	1.4616 (18)	C22—H22	0.9300
C4—C12	1.533 (2)	C23—O3	1.3609 (17)
C4—C5	1.564 (2)	C24—O3	1.4360 (18)
C5—O1	1.2079 (19)	C24—C25	1.507 (2)
C5—C6	1.482 (2)	C24—H24A	0.9700
C6—C7	1.370 (3)	C24—H24B	0.9700
C6—C11	1.409 (3)	C25—C26	1.520 (3)
C7—C8	1.420 (4)	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C8—C9	1.368 (4)	C26—C27	1.510 (3)
C8—H8	0.9300	C26—H26A	0.9700
C9—C10	1.407 (4)	C26—H26B	0.9700
C9—H9	0.9300	C27—O4	1.4372 (19)
C10—C11	1.412 (2)	C27—H27A	0.9700
C10—C15	1.418 (4)	C27—H27B	0.9700
C11—C12	1.399 (2)	C28—O4	1.3640 (19)
C12—C13	1.365 (2)	C28—C29	1.388 (2)
C13—C14	1.412 (3)	C28—C33	1.405 (2)
C13—H13	0.9300	C29—C30	1.378 (3)
C14—C15	1.345 (4)	C29—H29	0.9300
C14—H14	0.9300	C30—C31	1.369 (3)
C15—H15	0.9300	C30—H30	0.9300
C16—N1	1.456 (2)	C31—C32	1.385 (3)
C16—H16A	0.9600	C31—H31	0.9300
C16—H16B	0.9600	C32—C33	1.389 (2)
C16—H16C	0.9600	C32—H32	0.9300
C17—O2	1.2165 (17)
N1—C1—C2	105.89 (12)	C19—C18—C23	118.57 (14)
N1—C1—H1A	110.6	C19—C18—C17	117.88 (14)
C2—C1—H1A	110.6	C23—C18—C17	123.51 (13)
N1—C1—H1B	110.6	C20—C19—C18	121.12 (17)
C2—C1—H1B	110.6	C20—C19—H19	119.4
H1A—C1—H1B	108.7	C18—C19—H19	119.4
C33—C2—C3	115.53 (12)	C21—C20—C19	119.44 (17)
C33—C2—C1	117.14 (13)	C21—C20—H20	120.3
C3—C2—C1	102.89 (12)	C19—C20—H20	120.3
C33—C2—H2	106.9	C20—C21—C22	120.97 (17)
C3—C2—H2	106.9	C20—C21—H21	119.5
C1—C2—H2	106.9	C22—C21—H21	119.5
C17—C3—C2	115.55 (12)	C21—C22—C23	120.21 (17)
C17—C3—C4	112.42 (11)	C21—C22—H22	119.9
C2—C3—C4	101.87 (11)	C23—C22—H22	119.9
C17—C3—H3	108.9	O3—C23—C22	123.56 (14)
C2—C3—H3	108.9	O3—C23—C18	116.75 (12)
C4—C3—H3	108.9	C22—C23—C18	119.62 (14)
N1—C4—C12	116.98 (12)	O3—C24—C25	106.31 (13)
N1—C4—C3	99.72 (11)	O3—C24—H24A	110.5
C12—C4—C3	114.99 (12)	C25—C24—H24A	110.5
N1—C4—C5	111.72 (12)	O3—C24—H24B	110.5
C12—C4—C5	102.82 (12)	C25—C24—H24B	110.5
C3—C4—C5	110.94 (12)	H24A—C24—H24B	108.7
O1—C5—C6	128.49 (16)	C24—C25—C26	113.63 (16)
O1—C5—C4	124.00 (14)	C24—C25—H25A	108.8
C6—C5—C4	107.52 (13)	C26—C25—H25A	108.8
C7—C6—C11	120.19 (18)	C24—C25—H25B	108.8
C7—C6—C5	132.5 (2)	C26—C25—H25B	108.8
C11—C6—C5	107.26 (15)	H25A—C25—H25B	107.7
C6—C7—C8	117.2 (3)	C27—C26—C25	114.63 (16)
C6—C7—H7	121.4	C27—C26—H26A	108.6
C8—C7—H7	121.4	C25—C26—H26A	108.6
C9—C8—C7	122.8 (2)	C27—C26—H26B	108.6
C9—C8—H8	118.6	C25—C26—H26B	108.6
C7—C8—H8	118.6	H26A—C26—H26B	107.6
C8—C9—C10	121.2 (2)	O4—C27—C26	109.63 (13)
C8—C9—H9	119.4	O4—C27—H27A	109.7
C10—C9—H9	119.4	C26—C27—H27A	109.7
C9—C10—C11	115.6 (2)	O4—C27—H27B	109.7
C9—C10—C15	128.0 (2)	C26—C27—H27B	109.7
C11—C10—C15	116.4 (2)	H27A—C27—H27B	108.2
C12—C11—C6	113.94 (14)	O4—C28—C29	125.17 (15)
C12—C11—C10	123.1 (2)	O4—C28—C33	114.55 (14)
C6—C11—C10	122.95 (19)	C29—C28—C33	120.27 (16)
C13—C12—C11	118.37 (16)	C30—C29—C28	120.15 (18)
C13—C12—C4	133.39 (16)	C30—C29—H29	119.9
C11—C12—C4	108.24 (14)	C28—C29—H29	119.9
C12—C13—C14	119.3 (2)	C31—C30—C29	120.66 (18)
C12—C13—H13	120.3	C31—C30—H30	119.7
C14—C13—H13	120.3	C29—C30—H30	119.7
C15—C14—C13	122.7 (2)	C30—C31—C32	119.37 (18)
C15—C14—H14	118.6	C30—C31—H31	120.3
C13—C14—H14	118.6	C32—C31—H31	120.3
C14—C15—C10	120.09 (19)	C31—C32—C33	121.86 (18)
C14—C15—H15	120.0	C31—C32—H32	119.1
C10—C15—H15	120.0	C33—C32—H32	119.1
N1—C16—H16A	109.5	C32—C33—C28	117.69 (16)
N1—C16—H16B	109.5	C32—C33—C2	119.58 (15)
H16A—C16—H16B	109.5	C28—C33—C2	122.73 (14)
N1—C16—H16C	109.5	C16—N1—C4	115.89 (14)
H16A—C16—H16C	109.5	C16—N1—C1	115.79 (15)
H16B—C16—H16C	109.5	C4—N1—C1	108.04 (12)
O2—C17—C18	119.55 (13)	C23—O3—C24	119.06 (12)
O2—C17—C3	121.26 (13)	C28—O4—C27	123.29 (13)
C18—C17—C3	119.01 (12)
N1—C1—C2—C33	−136.90 (13)	C2—C3—C17—O2	−22.5 (2)
N1—C1—C2—C3	−9.01 (15)	C4—C3—C17—O2	93.80 (17)
C33—C2—C3—C17	−75.61 (16)	C2—C3—C17—C18	162.43 (12)
C1—C2—C3—C17	155.49 (12)	C4—C3—C17—C18	−81.22 (15)
C33—C2—C3—C4	162.22 (12)	O2—C17—C18—C19	−45.8 (2)
C1—C2—C3—C4	33.32 (14)	C3—C17—C18—C19	129.27 (15)
C17—C3—C4—N1	−169.82 (11)	O2—C17—C18—C23	131.81 (16)
C2—C3—C4—N1	−45.52 (13)	C3—C17—C18—C23	−53.1 (2)
C17—C3—C4—C12	−43.82 (17)	C23—C18—C19—C20	−0.4 (2)
C2—C3—C4—C12	80.48 (14)	C17—C18—C19—C20	177.41 (16)
C17—C3—C4—C5	72.31 (14)	C18—C19—C20—C21	−1.7 (3)
C2—C3—C4—C5	−163.39 (11)	C19—C20—C21—C22	1.7 (3)
N1—C4—C5—O1	−49.2 (2)	C20—C21—C22—C23	0.4 (3)
C12—C4—C5—O1	−175.47 (16)	C21—C22—C23—O3	−179.41 (15)
C3—C4—C5—O1	61.1 (2)	C21—C22—C23—C18	−2.5 (2)
N1—C4—C5—C6	130.97 (13)	C19—C18—C23—O3	179.58 (13)
C12—C4—C5—C6	4.71 (15)	C17—C18—C23—O3	1.9 (2)
C3—C4—C5—C6	−118.73 (13)	C19—C18—C23—C22	2.5 (2)
O1—C5—C6—C7	−4.9 (3)	C17—C18—C23—C22	−175.18 (14)
C4—C5—C6—C7	175.0 (2)	O3—C24—C25—C26	71.99 (18)
O1—C5—C6—C11	175.99 (17)	C24—C25—C26—C27	−135.12 (16)
C4—C5—C6—C11	−4.20 (17)	C25—C26—C27—O4	74.2 (2)
C11—C6—C7—C8	−0.7 (3)	O4—C28—C29—C30	−178.10 (15)
C5—C6—C7—C8	−179.8 (2)	C33—C28—C29—C30	0.5 (3)
C6—C7—C8—C9	−1.7 (4)	C28—C29—C30—C31	0.1 (3)
C7—C8—C9—C10	2.2 (4)	C29—C30—C31—C32	−0.5 (3)
C8—C9—C10—C11	−0.1 (3)	C30—C31—C32—C33	0.2 (3)
C8—C9—C10—C15	179.2 (2)	C31—C32—C33—C28	0.4 (2)
C7—C6—C11—C12	−177.33 (17)	C31—C32—C33—C2	−178.72 (16)
C5—C6—C11—C12	1.9 (2)	O4—C28—C33—C32	178.01 (14)
C7—C6—C11—C10	2.8 (3)	C29—C28—C33—C32	−0.8 (2)
C5—C6—C11—C10	−177.89 (16)	O4—C28—C33—C2	−2.9 (2)
C9—C10—C11—C12	177.83 (18)	C29—C28—C33—C2	178.32 (15)
C15—C10—C11—C12	−1.6 (3)	C3—C2—C33—C32	117.19 (16)
C9—C10—C11—C6	−2.3 (3)	C1—C2—C33—C32	−121.30 (16)
C15—C10—C11—C6	178.22 (17)	C3—C2—C33—C28	−61.87 (19)
C6—C11—C12—C13	−178.50 (15)	C1—C2—C33—C28	59.65 (19)
C10—C11—C12—C13	1.3 (3)	C12—C4—N1—C16	48.6 (2)
C6—C11—C12—C4	1.21 (19)	C3—C4—N1—C16	173.22 (14)
C10—C11—C12—C4	−178.95 (15)	C5—C4—N1—C16	−69.49 (17)
N1—C4—C12—C13	53.2 (2)	C12—C4—N1—C1	−83.20 (16)
C3—C4—C12—C13	−63.3 (2)	C3—C4—N1—C1	41.42 (14)
C5—C4—C12—C13	176.04 (18)	C5—C4—N1—C1	158.71 (12)
N1—C4—C12—C11	−126.41 (15)	C2—C1—N1—C16	−152.69 (14)
C3—C4—C12—C11	117.08 (14)	C2—C1—N1—C4	−20.84 (16)
C5—C4—C12—C11	−3.61 (15)	C22—C23—O3—C24	−1.9 (2)
C11—C12—C13—C14	0.0 (3)	C18—C23—O3—C24	−178.90 (14)
C4—C12—C13—C14	−179.62 (17)	C25—C24—O3—C23	−178.90 (14)
C12—C13—C14—C15	−1.0 (3)	C29—C28—O4—C27	−8.9 (2)
C13—C14—C15—C10	0.7 (3)	C33—C28—O4—C27	172.38 (13)
C9—C10—C15—C14	−178.8 (2)	C26—C27—O4—C28	−107.64 (17)
C11—C10—C15—C14	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1i	0.93	2.62	3.535 (3)	167
C15—H15···O1i	0.93	2.50	3.414 (2)	168
C27—H27B···O2ii	0.97	2.48	3.403 (2)	158
C29—H29···O2ii	0.93	2.57	3.450 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1i	0.93	2.62	3.535 (3)	167
C15—H15⋯O1i	0.93	2.50	3.414 (2)	168
C27—H27B⋯O2ii	0.97	2.48	3.403 (2)	158
C29—H29⋯O2ii	0.93	2.57	3.450 (2)	159

Symmetry codes: (i) ; (ii) .