1-(4-Methoxy-phen-yl)-7-phenyl-3-(phenyl-selenylmeth-yl)perhydro-isoxazolo[2',3':1,2]pyrrolo[3,4-b]azetidine-6-spiro-2'-chroman-2,4'-dione.

In the title compound, C(35)H(30)N(2)O(5)Se, the pyrrolidine ring adopts an envelope conformation and the oxazolidine ring is in a twist conformation. The tetra-hydro-pyran ring adopts a half-chair conformation. The methoxy-phenyl ring is twisted away from the attached azetidinone ring by 15.7 (1)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into a two-dimensional network.

Related literature

For general background, see: Brakhage (1998 ▶); Chenera et al. (1993 ▶); Ellis (1997 ▶); Farrugia (1997 ▶); Kilonda et al. (1995 ▶); Koojiman et al. (1984 ▶); Lampronti et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformation details, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C35H30N2O5Se

M = 637.57

Monoclinic,

a = 14.0886 (5) Å

b = 10.6813 (4) Å

c = 19.4744 (7) Å

β = 92.721 (2)°

V = 2927.29 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.33 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.691, T max = 0.777

38750 measured reflections

9941 independent reflections

5805 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.116

S = 1.01

9941 reflections

389 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008829/ci2571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008829/ci2571Isup2.hkl

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

C35H30N2O5Se	F000 = 1312
Mr = 637.57	Dx = 1.447 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 38750 reflections
a = 14.0886 (5) Å	θ = 1.8–31.9º
b = 10.6813 (4) Å	µ = 1.33 mm−1
c = 19.4744 (7) Å	T = 293 (2) K
β = 92.721 (2)º	Prism, colourless
V = 2927.29 (18) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker KappaAPEX2 diffractometer	9941 independent reflections
Radiation source: fine-focus sealed tube	5805 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 293(2) K	θmax = 31.9º
ω and φ scans	θmin = 1.8º
Absorption correction: multi-scan(Blessing, 1995)	h = −19→20
Tmin = 0.691, Tmax = 0.777	k = −15→10
38750 measured reflections	l = −28→28

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) = 0.116	w = 1/[σ2(Fo2) + (0.0444P)2 + 1.2941P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
9941 reflections	Δρmax = 0.79 e Å−3
389 parameters	Δρmin = −0.67 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
Se1	1.016999 (16)	0.19600 (3)	0.180072 (11)	0.05427 (9)
O1	0.84548 (10)	0.24863 (15)	0.33002 (7)	0.0499 (4)
O2	0.69775 (9)	0.13919 (14)	0.07844 (6)	0.0423 (3)
O3	0.64805 (13)	0.40844 (15)	0.12826 (7)	0.0583 (4)
O4	0.54329 (11)	0.16190 (14)	−0.01690 (7)	0.0482 (4)
O5	0.42581 (12)	0.20236 (17)	0.48343 (9)	0.0662 (5)
N1	0.71402 (11)	0.11790 (15)	0.30571 (7)	0.0353 (3)
N2	0.74055 (11)	0.06570 (15)	0.13393 (7)	0.0358 (3)
C1	0.80284 (13)	0.16622 (18)	0.30008 (9)	0.0359 (4)
C2	0.82270 (13)	0.07814 (18)	0.24043 (9)	0.0357 (4)
H2	0.8749	0.0189	0.2497	0.043*
C3	0.72246 (13)	0.02471 (18)	0.25094 (9)	0.0354 (4)
H3	0.7221	−0.0623	0.2669	0.042*
C4	0.81961 (13)	0.13643 (18)	0.16898 (9)	0.0343 (4)
H4	0.8039	0.2256	0.1714	0.041*
C5	0.66549 (13)	0.04692 (18)	0.18298 (9)	0.0346 (4)
H5	0.6280	−0.0276	0.1704	0.041*
C6	0.60958 (12)	0.19551 (17)	0.09998 (9)	0.0322 (4)
C7	0.60343 (12)	0.16392 (17)	0.17651 (9)	0.0324 (4)
H7	0.6359	0.2308	0.2028	0.039*
C8	0.62051 (13)	0.33430 (18)	0.08468 (9)	0.0352 (4)
C9	0.60212 (13)	0.36900 (18)	0.01199 (9)	0.0357 (4)
C10	0.62385 (15)	0.4882 (2)	−0.01152 (11)	0.0458 (5)
H10	0.6456	0.5490	0.0195	0.055*
C11	0.61339 (18)	0.5166 (2)	−0.08025 (12)	0.0552 (6)
H11	0.6283	0.5963	−0.0957	0.066*
C12	0.58075 (18)	0.4265 (2)	−0.12602 (11)	0.0580 (6)
H12	0.5743	0.4459	−0.1726	0.070*
C13	0.55774 (17)	0.3095 (2)	−0.10459 (11)	0.0525 (6)
H13	0.5355	0.2498	−0.1362	0.063*
C14	0.56779 (14)	0.27993 (19)	−0.03503 (10)	0.0396 (4)
C15	0.52914 (14)	0.1432 (2)	0.05444 (10)	0.0421 (4)
H15A	0.5232	0.0542	0.0633	0.051*
H15B	0.4702	0.1830	0.0661	0.051*
C16	0.50369 (13)	0.1537 (2)	0.20162 (10)	0.0412 (4)
C17	0.45117 (18)	0.0450 (3)	0.19745 (14)	0.0660 (7)
H17	0.4770	−0.0262	0.1781	0.079*
C18	0.3608 (2)	0.0404 (4)	0.22162 (16)	0.0898 (11)
H18	0.3265	−0.0339	0.2186	0.108*
C19	0.3214 (2)	0.1434 (5)	0.24973 (16)	0.0944 (12)
H19	0.2604	0.1396	0.2659	0.113*
C20	0.3719 (2)	0.2522 (4)	0.25400 (15)	0.0848 (10)
H20	0.3450	0.3229	0.2730	0.102*
C21	0.46266 (16)	0.2584 (3)	0.23037 (12)	0.0561 (6)
H21	0.4965	0.3331	0.2337	0.067*
C22	0.64158 (13)	0.13740 (18)	0.35180 (9)	0.0355 (4)
C23	0.57163 (15)	0.0489 (2)	0.35695 (10)	0.0455 (5)
H23	0.5739	−0.0240	0.3309	0.055*
C24	0.49788 (16)	0.0667 (2)	0.40035 (11)	0.0491 (5)
H24	0.4507	0.0063	0.4035	0.059*
C25	0.49483 (14)	0.1746 (2)	0.43884 (10)	0.0448 (5)
C26	0.56613 (15)	0.2627 (2)	0.43419 (11)	0.0474 (5)
H26	0.5647	0.3348	0.4608	0.057*
C27	0.63907 (14)	0.2453 (2)	0.39089 (10)	0.0424 (4)
H27	0.6864	0.3055	0.3879	0.051*
C28	0.34568 (18)	0.1226 (3)	0.48395 (15)	0.0736 (8)
H28A	0.3016	0.1544	0.5158	0.110*
H28B	0.3655	0.0400	0.4977	0.110*
H28C	0.3156	0.1194	0.4387	0.110*
C29	0.90857 (14)	0.1174 (2)	0.13028 (10)	0.0441 (5)
H29A	0.9003	0.1540	0.0848	0.053*
H29B	0.9205	0.0286	0.1250	0.053*
C30	1.11387 (14)	0.1421 (2)	0.12143 (10)	0.0423 (4)
C31	1.12365 (18)	0.0189 (2)	0.10270 (15)	0.0628 (7)
H31	1.0823	−0.0412	0.1187	0.075*
C32	1.19504 (19)	−0.0161 (3)	0.05994 (17)	0.0766 (8)
H32	1.2007	−0.0994	0.0468	0.092*
C33	1.25653 (18)	0.0703 (3)	0.03718 (14)	0.0715 (8)
H33	1.3050	0.0461	0.0092	0.086*
C34	1.24733 (17)	0.1910 (3)	0.05514 (14)	0.0641 (7)
H34	1.2893	0.2502	0.0391	0.077*
C35	1.17647 (15)	0.2283 (2)	0.09712 (12)	0.0523 (5)
H35	1.1710	0.3122	0.1090	0.063*

	U11	U22	U33	U12	U13	U23
Se1	0.04250 (13)	0.07341 (18)	0.04728 (13)	0.00234 (11)	0.00606 (9)	−0.01202 (11)
O1	0.0460 (8)	0.0529 (9)	0.0506 (8)	−0.0080 (7)	0.0006 (7)	−0.0064 (7)
O2	0.0403 (7)	0.0574 (9)	0.0294 (6)	0.0159 (6)	0.0042 (5)	−0.0001 (6)
O3	0.0896 (12)	0.0422 (9)	0.0416 (8)	−0.0170 (8)	−0.0122 (8)	−0.0078 (7)
O4	0.0623 (9)	0.0430 (8)	0.0380 (7)	−0.0094 (7)	−0.0108 (6)	−0.0066 (6)
O5	0.0488 (9)	0.0835 (13)	0.0684 (11)	−0.0043 (8)	0.0253 (8)	−0.0200 (9)
N1	0.0391 (8)	0.0353 (9)	0.0317 (7)	0.0000 (7)	0.0052 (6)	−0.0020 (6)
N2	0.0373 (8)	0.0384 (9)	0.0318 (7)	0.0091 (7)	0.0030 (6)	−0.0002 (6)
C1	0.0366 (10)	0.0386 (11)	0.0324 (8)	0.0039 (8)	0.0002 (7)	0.0068 (8)
C2	0.0367 (9)	0.0369 (11)	0.0337 (8)	0.0093 (8)	0.0030 (7)	0.0043 (8)
C3	0.0426 (10)	0.0296 (9)	0.0343 (8)	0.0053 (8)	0.0064 (7)	0.0023 (7)
C4	0.0346 (9)	0.0366 (10)	0.0320 (8)	0.0071 (8)	0.0037 (7)	0.0019 (7)
C5	0.0356 (9)	0.0316 (10)	0.0368 (9)	0.0018 (7)	0.0043 (7)	−0.0045 (7)
C6	0.0291 (8)	0.0354 (10)	0.0319 (8)	0.0033 (7)	−0.0003 (6)	−0.0067 (7)
C7	0.0290 (8)	0.0338 (10)	0.0346 (8)	0.0012 (7)	0.0026 (7)	−0.0051 (7)
C8	0.0329 (9)	0.0366 (10)	0.0359 (9)	−0.0005 (8)	−0.0018 (7)	−0.0051 (8)
C9	0.0328 (9)	0.0370 (11)	0.0370 (9)	0.0044 (8)	−0.0031 (7)	−0.0028 (8)
C10	0.0509 (12)	0.0403 (12)	0.0460 (11)	0.0000 (9)	−0.0015 (9)	−0.0025 (9)
C11	0.0664 (15)	0.0471 (13)	0.0518 (12)	0.0032 (11)	−0.0001 (11)	0.0106 (11)
C12	0.0684 (16)	0.0632 (16)	0.0415 (11)	0.0064 (13)	−0.0073 (10)	0.0058 (11)
C13	0.0604 (14)	0.0559 (15)	0.0397 (10)	0.0007 (11)	−0.0131 (10)	−0.0056 (10)
C14	0.0369 (10)	0.0424 (12)	0.0386 (9)	0.0031 (8)	−0.0077 (8)	−0.0047 (8)
C15	0.0442 (11)	0.0393 (11)	0.0422 (10)	−0.0072 (9)	−0.0047 (8)	−0.0056 (9)
C16	0.0327 (10)	0.0552 (13)	0.0360 (9)	0.0011 (9)	0.0044 (7)	−0.0014 (9)
C17	0.0502 (14)	0.0756 (18)	0.0733 (16)	−0.0166 (13)	0.0132 (12)	−0.0070 (14)
C18	0.0539 (17)	0.138 (3)	0.0782 (19)	−0.0374 (19)	0.0110 (15)	0.004 (2)
C19	0.0363 (14)	0.181 (4)	0.0671 (18)	0.004 (2)	0.0132 (12)	0.010 (2)
C20	0.0533 (17)	0.134 (3)	0.0680 (17)	0.0316 (19)	0.0163 (14)	−0.0062 (19)
C21	0.0462 (13)	0.0687 (16)	0.0539 (12)	0.0178 (11)	0.0093 (10)	−0.0033 (12)
C22	0.0382 (10)	0.0385 (11)	0.0299 (8)	0.0018 (8)	0.0021 (7)	0.0019 (8)
C23	0.0525 (12)	0.0419 (12)	0.0431 (10)	−0.0058 (9)	0.0124 (9)	−0.0067 (9)
C24	0.0471 (12)	0.0500 (13)	0.0512 (12)	−0.0109 (10)	0.0115 (9)	−0.0024 (10)
C25	0.0365 (10)	0.0601 (14)	0.0384 (10)	0.0029 (9)	0.0075 (8)	−0.0040 (9)
C26	0.0467 (12)	0.0502 (13)	0.0457 (11)	−0.0004 (10)	0.0073 (9)	−0.0151 (10)
C27	0.0419 (11)	0.0432 (11)	0.0424 (10)	−0.0050 (9)	0.0049 (8)	−0.0083 (9)
C28	0.0448 (14)	0.099 (2)	0.0793 (18)	−0.0042 (14)	0.0260 (12)	−0.0061 (16)
C29	0.0366 (10)	0.0604 (14)	0.0359 (9)	0.0025 (9)	0.0062 (8)	−0.0018 (9)
C30	0.0331 (10)	0.0500 (12)	0.0437 (10)	0.0037 (9)	−0.0003 (8)	−0.0039 (9)
C31	0.0492 (13)	0.0477 (14)	0.0919 (19)	−0.0018 (11)	0.0087 (13)	−0.0055 (13)
C32	0.0586 (16)	0.0615 (17)	0.110 (2)	0.0086 (13)	0.0066 (15)	−0.0344 (16)
C33	0.0411 (13)	0.099 (2)	0.0751 (17)	−0.0032 (14)	0.0079 (12)	−0.0348 (16)
C34	0.0431 (13)	0.085 (2)	0.0653 (15)	−0.0131 (12)	0.0090 (11)	−0.0100 (14)
C35	0.0420 (12)	0.0548 (14)	0.0601 (13)	−0.0032 (10)	0.0028 (10)	−0.0081 (11)

Se1—C30	1.910 (2)	C13—H13	0.93
Se1—C29	1.959 (2)	C15—H15A	0.97
O1—C1	1.201 (2)	C15—H15B	0.97
O2—N2	1.4441 (19)	C16—C17	1.377 (3)
O2—C6	1.460 (2)	C16—C21	1.389 (3)
O3—C8	1.211 (2)	C17—C18	1.379 (4)
O4—C14	1.358 (2)	C17—H17	0.93
O4—C15	1.427 (2)	C18—C19	1.359 (5)
O5—C25	1.367 (2)	C18—H18	0.93
O5—C28	1.414 (3)	C19—C20	1.364 (5)
N1—C1	1.363 (2)	C19—H19	0.93
N1—C22	1.406 (2)	C20—C21	1.381 (4)
N1—C3	1.468 (2)	C20—H20	0.93
N2—C5	1.472 (2)	C21—H21	0.93
N2—C4	1.485 (2)	C22—C23	1.373 (3)
C1—C2	1.531 (3)	C22—C27	1.382 (3)
C2—C4	1.523 (2)	C23—C24	1.383 (3)
C2—C3	1.546 (3)	C23—H23	0.93
C2—H2	0.98	C24—C25	1.376 (3)
C3—C5	1.533 (3)	C24—H24	0.93
C3—H3	0.98	C25—C26	1.382 (3)
C4—C29	1.506 (3)	C26—C27	1.372 (3)
C4—H4	0.98	C26—H26	0.93
C5—C7	1.527 (3)	C27—H27	0.93
C5—H5	0.98	C28—H28A	0.96
C6—C15	1.513 (2)	C28—H28B	0.96
C6—C8	1.521 (3)	C28—H28C	0.96
C6—C7	1.535 (2)	C29—H29A	0.97
C7—C16	1.513 (2)	C29—H29B	0.97
C7—H7	0.98	C30—C31	1.374 (3)
C8—C9	1.474 (3)	C30—C35	1.375 (3)
C9—C14	1.391 (3)	C31—C32	1.387 (4)
C9—C10	1.392 (3)	C31—H31	0.93
C10—C11	1.374 (3)	C32—C33	1.354 (4)
C10—H10	0.93	C32—H32	0.93
C11—C12	1.376 (3)	C33—C34	1.344 (4)
C11—H11	0.93	C33—H33	0.93
C12—C13	1.362 (3)	C34—C35	1.379 (3)
C12—H12	0.93	C34—H34	0.93
C13—C14	1.392 (3)	C35—H35	0.93
C30—Se1—C29	97.90 (8)	O4—C15—H15A	109.1
N2—O2—C6	109.86 (12)	C6—C15—H15A	109.1
C14—O4—C15	115.61 (15)	O4—C15—H15B	109.1
C25—O5—C28	117.78 (19)	C6—C15—H15B	109.1
C1—N1—C22	133.82 (16)	H15A—C15—H15B	107.8
C1—N1—C3	95.27 (14)	C17—C16—C21	118.0 (2)
C22—N1—C3	130.58 (16)	C17—C16—C7	123.1 (2)
O2—N2—C5	105.81 (13)	C21—C16—C7	118.9 (2)
O2—N2—C4	110.17 (14)	C16—C17—C18	120.8 (3)
C5—N2—C4	108.50 (13)	C16—C17—H17	119.6
O1—C1—N1	132.72 (18)	C18—C17—H17	119.6
O1—C1—C2	135.53 (18)	C19—C18—C17	120.7 (3)
N1—C1—C2	91.72 (15)	C19—C18—H18	119.7
C4—C2—C1	116.34 (16)	C17—C18—H18	119.7
C4—C2—C3	106.57 (14)	C18—C19—C20	119.5 (3)
C1—C2—C3	85.72 (13)	C18—C19—H19	120.2
C4—C2—H2	114.8	C20—C19—H19	120.2
C1—C2—H2	114.8	C19—C20—C21	120.6 (3)
C3—C2—H2	114.8	C19—C20—H20	119.7
N1—C3—C5	117.72 (15)	C21—C20—H20	119.7
N1—C3—C2	87.24 (14)	C20—C21—C16	120.4 (3)
C5—C3—C2	105.83 (14)	C20—C21—H21	119.8
N1—C3—H3	114.2	C16—C21—H21	119.8
C5—C3—H3	114.2	C23—C22—C27	119.77 (18)
C2—C3—H3	114.2	C23—C22—N1	119.34 (17)
N2—C4—C29	108.99 (15)	C27—C22—N1	120.88 (17)
N2—C4—C2	101.55 (14)	C22—C23—C24	120.83 (19)
C29—C4—C2	114.43 (15)	C22—C23—H23	119.6
N2—C4—H4	110.5	C24—C23—H23	119.6
C29—C4—H4	110.5	C25—C24—C23	119.5 (2)
C2—C4—H4	110.5	C25—C24—H24	120.3
N2—C5—C7	105.14 (15)	C23—C24—H24	120.3
N2—C5—C3	102.61 (14)	O5—C25—C24	124.7 (2)
C7—C5—C3	118.17 (15)	O5—C25—C26	115.79 (19)
N2—C5—H5	110.1	C24—C25—C26	119.50 (19)
C7—C5—H5	110.1	C27—C26—C25	121.1 (2)
C3—C5—H5	110.1	C27—C26—H26	119.5
O2—C6—C15	107.66 (14)	C25—C26—H26	119.5
O2—C6—C8	104.47 (14)	C26—C27—C22	119.4 (2)
C15—C6—C8	108.99 (15)	C26—C27—H27	120.3
O2—C6—C7	106.06 (13)	C22—C27—H27	120.3
C15—C6—C7	114.39 (15)	O5—C28—H28A	109.5
C8—C6—C7	114.54 (14)	O5—C28—H28B	109.5
C16—C7—C5	116.80 (16)	H28A—C28—H28B	109.5
C16—C7—C6	115.20 (15)	O5—C28—H28C	109.5
C5—C7—C6	101.63 (14)	H28A—C28—H28C	109.5
C16—C7—H7	107.5	H28B—C28—H28C	109.5
C5—C7—H7	107.5	C4—C29—Se1	110.03 (13)
C6—C7—H7	107.5	C4—C29—H29A	109.7
O3—C8—C9	122.98 (18)	Se1—C29—H29A	109.7
O3—C8—C6	122.14 (17)	C4—C29—H29B	109.7
C9—C8—C6	114.72 (15)	Se1—C29—H29B	109.7
C14—C9—C10	118.95 (18)	H29A—C29—H29B	108.2
C14—C9—C8	119.98 (18)	C31—C30—C35	118.4 (2)
C10—C9—C8	120.96 (17)	C31—C30—Se1	122.08 (17)
C11—C10—C9	120.5 (2)	C35—C30—Se1	119.48 (17)
C11—C10—H10	119.7	C30—C31—C32	120.1 (2)
C9—C10—H10	119.7	C30—C31—H31	119.9
C10—C11—C12	119.6 (2)	C32—C31—H31	119.9
C10—C11—H11	120.2	C33—C32—C31	120.4 (3)
C12—C11—H11	120.2	C33—C32—H32	119.8
C13—C12—C11	121.4 (2)	C31—C32—H32	119.8
C13—C12—H12	119.3	C34—C33—C32	119.8 (2)
C11—C12—H12	119.3	C34—C33—H33	120.1
C12—C13—C14	119.5 (2)	C32—C33—H33	120.1
C12—C13—H13	120.3	C33—C34—C35	120.9 (2)
C14—C13—H13	120.3	C33—C34—H34	119.6
O4—C14—C9	123.26 (17)	C35—C34—H34	119.6
O4—C14—C13	116.63 (17)	C30—C35—C34	120.3 (2)
C9—C14—C13	120.1 (2)	C30—C35—H35	119.8
O4—C15—C6	112.56 (16)	C34—C35—H35	119.8
C6—O2—N2—C5	15.91 (18)	C8—C9—C10—C11	174.9 (2)
C6—O2—N2—C4	−101.18 (16)	C9—C10—C11—C12	0.3 (3)
C22—N1—C1—O1	−6.5 (4)	C10—C11—C12—C13	0.5 (4)
C3—N1—C1—O1	179.8 (2)	C11—C12—C13—C14	−0.3 (4)
C22—N1—C1—C2	175.33 (19)	C15—O4—C14—C9	16.9 (3)
C3—N1—C1—C2	1.69 (14)	C15—O4—C14—C13	−163.62 (19)
O1—C1—C2—C4	−73.3 (3)	C10—C9—C14—O4	−178.98 (18)
N1—C1—C2—C4	104.78 (17)	C8—C9—C14—O4	4.8 (3)
O1—C1—C2—C3	−179.7 (2)	C10—C9—C14—C13	1.5 (3)
N1—C1—C2—C3	−1.60 (13)	C8—C9—C14—C13	−174.72 (19)
C1—N1—C3—C5	−108.13 (18)	C12—C13—C14—O4	179.7 (2)
C22—N1—C3—C5	77.9 (2)	C12—C13—C14—C9	−0.7 (3)
C1—N1—C3—C2	−1.67 (14)	C14—O4—C15—C6	−48.8 (2)
C22—N1—C3—C2	−175.64 (18)	O2—C6—C15—O4	−55.5 (2)
C4—C2—C3—N1	−114.74 (15)	C8—C6—C15—O4	57.3 (2)
C1—C2—C3—N1	1.49 (12)	C7—C6—C15—O4	−173.07 (16)
C4—C2—C3—C5	3.32 (19)	C5—C7—C16—C17	−32.9 (3)
C1—C2—C3—C5	119.55 (15)	C6—C7—C16—C17	86.3 (3)
O2—N2—C4—C29	−84.46 (17)	C5—C7—C16—C21	147.02 (19)
C5—N2—C4—C29	160.14 (15)	C6—C7—C16—C21	−93.8 (2)
O2—N2—C4—C2	154.42 (13)	C21—C16—C17—C18	−0.5 (4)
C5—N2—C4—C2	39.02 (17)	C7—C16—C17—C18	179.5 (2)
C1—C2—C4—N2	−118.02 (17)	C16—C17—C18—C19	0.4 (5)
C3—C2—C4—N2	−24.55 (18)	C17—C18—C19—C20	0.0 (5)
C1—C2—C4—C29	124.75 (19)	C18—C19—C20—C21	−0.3 (5)
C3—C2—C4—C29	−141.78 (17)	C19—C20—C21—C16	0.2 (4)
O2—N2—C5—C7	−31.16 (17)	C17—C16—C21—C20	0.1 (4)
C4—N2—C5—C7	87.05 (16)	C7—C16—C21—C20	−179.8 (2)
O2—N2—C5—C3	−155.33 (14)	C1—N1—C22—C23	−160.4 (2)
C4—N2—C5—C3	−37.13 (18)	C3—N1—C22—C23	11.3 (3)
N1—C3—C5—N2	114.86 (17)	C1—N1—C22—C27	20.8 (3)
C2—C3—C5—N2	19.55 (18)	C3—N1—C22—C27	−167.57 (18)
N1—C3—C5—C7	−0.2 (2)	C27—C22—C23—C24	0.6 (3)
C2—C3—C5—C7	−95.50 (18)	N1—C22—C23—C24	−178.19 (19)
N2—O2—C6—C15	−117.18 (16)	C22—C23—C24—C25	−0.1 (3)
N2—O2—C6—C8	127.06 (14)	C28—O5—C25—C24	−8.2 (3)
N2—O2—C6—C7	5.68 (18)	C28—O5—C25—C26	172.7 (2)
N2—C5—C7—C16	159.75 (15)	C23—C24—C25—O5	−179.9 (2)
C3—C5—C7—C16	−86.6 (2)	C23—C24—C25—C26	−0.8 (3)
N2—C5—C7—C6	33.51 (17)	O5—C25—C26—C27	−179.7 (2)
C3—C5—C7—C6	147.19 (16)	C24—C25—C26—C27	1.1 (3)
O2—C6—C7—C16	−151.09 (16)	C25—C26—C27—C22	−0.6 (3)
C15—C6—C7—C16	−32.6 (2)	C23—C22—C27—C26	−0.3 (3)
C8—C6—C7—C16	94.2 (2)	N1—C22—C27—C26	178.50 (18)
O2—C6—C7—C5	−23.81 (18)	N2—C4—C29—Se1	−174.50 (12)
C15—C6—C7—C5	94.68 (18)	C2—C4—C29—Se1	−61.6 (2)
C8—C6—C7—C5	−138.47 (15)	C30—Se1—C29—C4	175.59 (15)
O2—C6—C8—O3	−96.2 (2)	C29—Se1—C30—C31	−50.9 (2)
C15—C6—C8—O3	148.92 (19)	C29—Se1—C30—C35	129.36 (18)
C7—C6—C8—O3	19.3 (3)	C35—C30—C31—C32	−0.3 (4)
O2—C6—C8—C9	79.28 (18)	Se1—C30—C31—C32	180.0 (2)
C15—C6—C8—C9	−35.6 (2)	C30—C31—C32—C33	1.0 (4)
C7—C6—C8—C9	−165.14 (15)	C31—C32—C33—C34	−1.2 (5)
O3—C8—C9—C14	−178.1 (2)	C32—C33—C34—C35	0.6 (4)
C6—C8—C9—C14	6.5 (2)	C31—C30—C35—C34	−0.2 (3)
O3—C8—C9—C10	5.8 (3)	Se1—C30—C35—C34	179.50 (18)
C6—C8—C9—C10	−169.71 (17)	C33—C34—C35—C30	0.1 (4)
C14—C9—C10—C11	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.98	2.42	3.199 (3)	136
C29—H29A···O5ii	0.97	2.54	3.465 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.98	2.42	3.199 (3)	136
C29—H29A⋯O5ii	0.97	2.54	3.465 (3)	160

Symmetry codes: (i) ; (ii) .