3-(4-Chloro-phen-yl)-4-(4-methoxyphen-yl)-6-(phenyl-selenylmeth-yl)-2,3,3a,3b,4,5,5a,6,1'',2'',3'',4''-do-deca-hydro-azeto[2',3':3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2''-naphthalene-5,1''-dione.

In the title compound, C(36)H(31)ClN(2)O(4)Se, the four-membered β-lactam ring is fused to a pyrrolidine ring. The central five-membered ring of the fused tricyclic system exhibits an envelope conformation with the N atom as the flap, while the other five-membered ring exhibits a twist conformation. The chloro-phenyl ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions and the packing is further enhanced by C-H ⋯N inter-actions and π-π inter-actions between benzene rings of tetra-lone groups in mol-ecules related by an inversion center, with a centroid-centroid separation of 3.8923 (2) Å.

Related literature

For related literature, see: Allen et al. (1987 ▶); Amal Raj et al. (2003 ▶); Brakhage (1998 ▶); Cremer & Pople (1975 ▶); Kilonda et al. (1995 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C36H31ClN2O4Se

M = 670.04

Monoclinic,

a = 14.4697 (3) Å

b = 10.9493 (3) Å

c = 19.3011 (4) Å

β = 94.661 (1)°

V = 3047.82 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.36 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.24 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.671, T max = 0.720

37171 measured reflections

8699 independent reflections

5453 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.176

S = 1.02

8699 reflections

398 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); 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/S1600536808006570/bh2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006570/bh2162Isup2.hkl

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

C36H31ClN2O4Se	F000 = 1376
Mr = 670.04	Dx = 1.460 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 37171 reflections
a = 14.4697 (3) Å	θ = 1.7–29.8º
b = 10.9493 (3) Å	µ = 1.36 mm−1
c = 19.3011 (4) Å	T = 293 (2) K
β = 94.661 (1)º	Prism, colourless
V = 3047.82 (12) Å3	0.30 × 0.30 × 0.24 mm
Z = 4

Bruker APEXII diffractometer	8699 independent reflections
Radiation source: fine-focus sealed tube	5453 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 293(2) K	θmax = 29.8º
ω and φ scans	θmin = 1.7º
Absorption correction: multi-scan(Blessing, 1995)	h = −20→19
Tmin = 0.671, Tmax = 0.720	k = −15→15
37171 measured reflections	l = −26→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.09P)2 + 1.6651P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.176	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.72 e Å−3
8699 reflections	Δρmin = −0.86 e Å−3
398 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (6)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
C1	0.70233 (19)	0.1671 (3)	0.69974 (13)	0.0414 (6)
C2	0.68196 (19)	0.0826 (2)	0.75936 (13)	0.0419 (6)
H2	0.6303	0.0261	0.7486	0.050*
C3	0.68566 (18)	0.1382 (3)	0.83223 (12)	0.0416 (6)
H3	0.7007	0.2254	0.8307	0.050*
C4	0.83576 (18)	0.0507 (2)	0.82017 (12)	0.0383 (5)
H4	0.8742	−0.0205	0.8336	0.046*
C5	0.77879 (19)	0.0276 (2)	0.75107 (12)	0.0405 (5)
H5	0.7777	−0.0580	0.7361	0.049*
C6	0.85780 (18)	0.1320 (2)	0.64929 (12)	0.0398 (6)
C7	0.9257 (2)	0.0452 (3)	0.64583 (14)	0.0480 (6)
H7	0.9233	−0.0258	0.6721	0.058*
C8	0.9979 (2)	0.0618 (3)	0.60390 (15)	0.0534 (7)
H8	1.0437	0.0025	0.6021	0.064*
C9	1.0015 (2)	0.1668 (3)	0.56475 (15)	0.0520 (7)
C10	0.9323 (2)	0.2523 (3)	0.56705 (16)	0.0556 (7)
H10	0.9337	0.3220	0.5396	0.067*
C11	0.8610 (2)	0.2368 (3)	0.60915 (15)	0.0487 (6)
H11	0.8152	0.2962	0.6107	0.058*
C12	1.1467 (3)	0.1143 (5)	0.5225 (2)	0.0798 (11)
H12A	1.1883	0.1430	0.4897	0.120*
H12B	1.1266	0.0331	0.5100	0.120*
H12C	1.1781	0.1135	0.5682	0.120*
C13	0.89041 (17)	0.1991 (2)	0.90386 (12)	0.0330 (5)
C14	0.87399 (17)	0.3350 (2)	0.91654 (13)	0.0371 (5)
C15	0.89318 (17)	0.3797 (2)	0.98876 (13)	0.0371 (5)
C16	0.8704 (2)	0.5000 (3)	1.00480 (17)	0.0519 (7)
H16	0.8441	0.5516	0.9704	0.062*
C17	0.8873 (3)	0.5414 (3)	1.07230 (19)	0.0643 (9)
H17	0.8713	0.6209	1.0833	0.077*
C18	0.9270 (2)	0.4672 (3)	1.12289 (17)	0.0623 (9)
H18	0.9381	0.4966	1.1680	0.075*
C19	0.9505 (2)	0.3509 (3)	1.10802 (14)	0.0495 (7)
H19	0.9783	0.3013	1.1429	0.059*
C20	0.93320 (17)	0.3050 (2)	1.04094 (13)	0.0389 (5)
C21	0.9594 (2)	0.1759 (3)	1.02692 (14)	0.0494 (7)
H21A	0.9114	0.1219	1.0413	0.059*
H21B	1.0165	0.1563	1.0545	0.059*
C22	0.9726 (2)	0.1536 (2)	0.95051 (13)	0.0425 (6)
H22A	1.0283	0.1950	0.9384	0.051*
H22B	0.9807	0.0668	0.9429	0.051*
C23	0.89336 (16)	0.1679 (2)	0.82651 (12)	0.0337 (5)
H23	0.8584	0.2313	0.7999	0.040*
C24	0.98856 (18)	0.1624 (3)	0.80023 (13)	0.0444 (6)
C25	1.0212 (2)	0.2641 (3)	0.76751 (15)	0.0563 (8)
H25	0.9843	0.3337	0.7630	0.068*
C26	1.1072 (3)	0.2648 (5)	0.74137 (19)	0.0852 (14)
H26	1.1281	0.3345	0.7199	0.102*
C27	1.1604 (3)	0.1645 (6)	0.74713 (19)	0.0958 (18)
C28	1.1314 (3)	0.0618 (6)	0.7789 (2)	0.0966 (17)
H28	1.1695	−0.0068	0.7827	0.116*
C29	1.0447 (3)	0.0594 (4)	0.80593 (18)	0.0716 (10)
H29	1.0247	−0.0106	0.8275	0.086*
C30	0.5995 (2)	0.1179 (4)	0.87015 (15)	0.0565 (8)
H30A	0.6075	0.1552	0.9158	0.068*
H30B	0.5898	0.0310	0.8762	0.068*
C31	0.4002 (2)	0.1351 (3)	0.87652 (14)	0.0495 (7)
C32	0.3946 (3)	0.0177 (4)	0.9000 (2)	0.0728 (10)
H32	0.4378	−0.0398	0.8878	0.087*
C33	0.3252 (3)	−0.0167 (4)	0.9417 (2)	0.0842 (12)
H33	0.3226	−0.0970	0.9572	0.101*
C34	0.2633 (3)	0.0623 (5)	0.9598 (2)	0.0851 (13)
H34	0.2168	0.0375	0.9873	0.102*
C35	0.2670 (3)	0.1785 (5)	0.9386 (2)	0.0879 (14)
H35	0.2237	0.2344	0.9525	0.106*
C36	0.3345 (2)	0.2166 (4)	0.8964 (2)	0.0695 (10)
H36	0.3356	0.2973	0.8815	0.083*
N1	0.78743 (16)	0.1158 (2)	0.69470 (10)	0.0394 (5)
N2	0.76374 (16)	0.0684 (2)	0.86869 (10)	0.0419 (5)
O1	0.80695 (13)	0.13881 (18)	0.92556 (9)	0.0450 (4)
O2	0.84345 (18)	0.4012 (2)	0.87024 (11)	0.0628 (6)
O3	1.06894 (17)	0.1926 (3)	0.52152 (14)	0.0757 (8)
O4	0.66189 (15)	0.2495 (2)	0.66906 (11)	0.0575 (5)
Cl1	1.26648 (8)	0.1614 (3)	0.71137 (7)	0.1700 (10)
Se1	0.49162 (2)	0.18861 (4)	0.817879 (17)	0.06640 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0462 (14)	0.0452 (15)	0.0319 (11)	−0.0076 (12)	−0.0014 (10)	−0.0051 (10)
C2	0.0448 (14)	0.0466 (15)	0.0340 (11)	−0.0163 (11)	0.0019 (10)	−0.0054 (10)
C3	0.0449 (14)	0.0480 (15)	0.0320 (11)	−0.0129 (12)	0.0034 (10)	−0.0024 (10)
C4	0.0470 (14)	0.0354 (12)	0.0322 (11)	−0.0041 (11)	0.0013 (10)	0.0024 (9)
C5	0.0547 (15)	0.0331 (12)	0.0335 (11)	−0.0091 (11)	0.0020 (10)	−0.0037 (9)
C6	0.0450 (14)	0.0462 (15)	0.0277 (11)	−0.0069 (11)	−0.0004 (9)	−0.0052 (10)
C7	0.0613 (17)	0.0437 (15)	0.0395 (13)	0.0033 (13)	0.0065 (12)	0.0004 (11)
C8	0.0556 (17)	0.0597 (18)	0.0456 (15)	0.0111 (14)	0.0082 (12)	−0.0044 (13)
C9	0.0452 (15)	0.069 (2)	0.0419 (14)	−0.0051 (14)	0.0051 (11)	0.0015 (13)
C10	0.0513 (17)	0.0624 (19)	0.0534 (16)	−0.0034 (15)	0.0055 (13)	0.0174 (15)
C11	0.0461 (15)	0.0539 (17)	0.0461 (14)	0.0023 (13)	0.0037 (11)	0.0076 (13)
C12	0.0520 (19)	0.116 (3)	0.073 (2)	0.006 (2)	0.0159 (17)	−0.004 (2)
C13	0.0358 (11)	0.0332 (12)	0.0295 (10)	−0.0023 (9)	−0.0003 (8)	0.0025 (9)
C14	0.0349 (12)	0.0385 (13)	0.0370 (12)	0.0038 (10)	−0.0020 (9)	0.0025 (10)
C15	0.0344 (12)	0.0364 (13)	0.0407 (12)	−0.0044 (10)	0.0051 (9)	−0.0012 (10)
C16	0.0573 (17)	0.0390 (15)	0.0604 (17)	0.0009 (13)	0.0109 (14)	−0.0014 (13)
C17	0.076 (2)	0.0462 (17)	0.072 (2)	−0.0042 (16)	0.0178 (18)	−0.0197 (16)
C18	0.069 (2)	0.069 (2)	0.0504 (17)	−0.0174 (17)	0.0099 (15)	−0.0185 (15)
C19	0.0516 (16)	0.0585 (18)	0.0381 (13)	−0.0102 (13)	0.0011 (11)	−0.0052 (12)
C20	0.0362 (12)	0.0446 (14)	0.0353 (12)	−0.0061 (10)	−0.0003 (9)	−0.0025 (10)
C21	0.0636 (18)	0.0473 (16)	0.0347 (12)	0.0094 (13)	−0.0108 (12)	0.0033 (11)
C22	0.0509 (15)	0.0379 (13)	0.0371 (12)	0.0117 (11)	−0.0074 (11)	0.0010 (10)
C23	0.0351 (11)	0.0353 (12)	0.0303 (10)	−0.0016 (9)	0.0003 (9)	0.0023 (9)
C24	0.0381 (13)	0.0622 (17)	0.0325 (11)	−0.0017 (12)	−0.0002 (10)	−0.0039 (11)
C25	0.0518 (17)	0.074 (2)	0.0443 (15)	−0.0194 (15)	0.0074 (12)	−0.0075 (14)
C26	0.053 (2)	0.152 (4)	0.0524 (19)	−0.036 (3)	0.0117 (16)	−0.008 (2)
C27	0.0392 (18)	0.209 (6)	0.0390 (17)	0.001 (3)	0.0041 (13)	−0.014 (3)
C28	0.063 (2)	0.169 (5)	0.057 (2)	0.057 (3)	0.0006 (18)	−0.007 (3)
C29	0.065 (2)	0.098 (3)	0.0516 (18)	0.032 (2)	0.0041 (15)	0.0042 (18)
C30	0.0450 (15)	0.086 (2)	0.0392 (14)	−0.0098 (15)	0.0051 (11)	0.0036 (14)
C31	0.0432 (14)	0.0645 (19)	0.0400 (13)	−0.0064 (13)	−0.0017 (11)	0.0043 (12)
C32	0.070 (2)	0.064 (2)	0.086 (3)	0.0009 (18)	0.0116 (19)	0.0029 (19)
C33	0.087 (3)	0.077 (3)	0.087 (3)	−0.023 (2)	0.004 (2)	0.027 (2)
C34	0.051 (2)	0.128 (4)	0.077 (3)	−0.011 (2)	0.0054 (17)	0.030 (3)
C35	0.050 (2)	0.125 (4)	0.090 (3)	0.015 (2)	0.0159 (19)	0.022 (3)
C36	0.0545 (19)	0.075 (2)	0.079 (2)	0.0053 (17)	0.0061 (17)	0.0215 (19)
N1	0.0482 (12)	0.0390 (11)	0.0307 (9)	−0.0051 (9)	0.0012 (8)	−0.0010 (8)
N2	0.0487 (12)	0.0452 (12)	0.0316 (10)	−0.0131 (10)	0.0020 (8)	−0.0011 (9)
O1	0.0508 (11)	0.0568 (11)	0.0272 (8)	−0.0179 (9)	0.0031 (7)	0.0000 (7)
O2	0.0903 (17)	0.0478 (12)	0.0468 (11)	0.0209 (11)	−0.0156 (11)	0.0064 (9)
O3	0.0550 (14)	0.102 (2)	0.0736 (16)	0.0021 (13)	0.0258 (12)	0.0183 (14)
O4	0.0554 (12)	0.0655 (14)	0.0514 (11)	0.0061 (11)	0.0031 (9)	0.0103 (11)
Cl1	0.0433 (5)	0.398 (3)	0.0709 (7)	0.0147 (10)	0.0161 (5)	−0.0191 (12)
Se1	0.0518 (2)	0.0977 (3)	0.0502 (2)	−0.00495 (17)	0.00749 (14)	0.01801 (17)

C1—O4	1.204 (3)	C17—C18	1.361 (5)
C1—N1	1.364 (4)	C17—H17	0.9300
C1—C2	1.523 (4)	C18—C19	1.355 (5)
C2—C3	1.529 (3)	C18—H18	0.9300
C2—C5	1.546 (4)	C19—C20	1.392 (4)
C2—H2	0.9800	C19—H19	0.9300
C3—N2	1.492 (4)	C20—C21	1.494 (4)
C3—C30	1.513 (4)	C21—C22	1.522 (4)
C3—H3	0.9800	C21—H21A	0.9700
C4—N2	1.469 (3)	C21—H21B	0.9700
C4—C23	1.529 (3)	C22—H22A	0.9700
C4—C5	1.531 (3)	C22—H22B	0.9700
C4—H4	0.9800	C23—C24	1.507 (4)
C5—N1	1.468 (3)	C23—H23	0.9800
C5—H5	0.9800	C24—C25	1.382 (4)
C6—C7	1.373 (4)	C24—C29	1.389 (5)
C6—C11	1.388 (4)	C25—C26	1.380 (5)
C6—N1	1.408 (3)	C25—H25	0.9300
C7—C8	1.384 (4)	C26—C27	1.341 (8)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.379 (4)	C27—C28	1.363 (7)
C8—H8	0.9300	C27—Cl1	1.734 (4)
C9—O3	1.364 (4)	C28—C29	1.398 (6)
C9—C10	1.374 (5)	C28—H28	0.9300
C10—C11	1.375 (4)	C29—H29	0.9300
C10—H10	0.9300	C30—Se1	1.949 (3)
C11—H11	0.9300	C30—H30A	0.9700
C12—O3	1.414 (5)	C30—H30B	0.9700
C12—H12A	0.9600	C31—C32	1.368 (5)
C12—H12B	0.9600	C31—C36	1.381 (5)
C12—H12C	0.9600	C31—Se1	1.902 (3)
C13—O1	1.467 (3)	C32—C33	1.389 (6)
C13—C22	1.516 (3)	C32—H32	0.9300
C13—C14	1.529 (3)	C33—C34	1.313 (7)
C13—C23	1.536 (3)	C33—H33	0.9300
C14—O2	1.206 (3)	C34—C35	1.339 (6)
C14—C15	1.482 (3)	C34—H34	0.9300
C15—C20	1.387 (4)	C35—C36	1.386 (6)
C15—C16	1.399 (4)	C35—H35	0.9300
C16—C17	1.382 (5)	C36—H36	0.9300
C16—H16	0.9300	N2—O1	1.442 (3)
O4—C1—N1	132.7 (3)	C20—C19—H19	119.8
O4—C1—C2	135.2 (3)	C15—C20—C19	119.7 (3)
N1—C1—C2	92.0 (2)	C15—C20—C21	121.6 (2)
C1—C2—C3	117.3 (2)	C19—C20—C21	118.7 (2)
C1—C2—C5	85.76 (19)	C20—C21—C22	112.4 (2)
C3—C2—C5	106.6 (2)	C20—C21—H21A	109.1
C1—C2—H2	114.5	C22—C21—H21A	109.1
C3—C2—H2	114.5	C20—C21—H21B	109.1
C5—C2—H2	114.5	C22—C21—H21B	109.1
N2—C3—C30	108.6 (2)	H21A—C21—H21B	107.9
N2—C3—C2	101.5 (2)	C13—C22—C21	111.6 (2)
C30—C3—C2	114.7 (2)	C13—C22—H22A	109.3
N2—C3—H3	110.6	C21—C22—H22A	109.3
C30—C3—H3	110.6	C13—C22—H22B	109.3
C2—C3—H3	110.6	C21—C22—H22B	109.3
N2—C4—C23	104.4 (2)	H22A—C22—H22B	108.0
N2—C4—C5	102.6 (2)	C24—C23—C4	116.5 (2)
C23—C4—C5	117.4 (2)	C24—C23—C13	115.8 (2)
N2—C4—H4	110.6	C4—C23—C13	101.93 (18)
C23—C4—H4	110.6	C24—C23—H23	107.4
C5—C4—H4	110.6	C4—C23—H23	107.4
N1—C5—C4	117.7 (2)	C13—C23—H23	107.4
N1—C5—C2	87.3 (2)	C25—C24—C29	118.1 (3)
C4—C5—C2	105.9 (2)	C25—C24—C23	118.5 (3)
N1—C5—H5	114.2	C29—C24—C23	123.4 (3)
C4—C5—H5	114.2	C26—C25—C24	121.5 (4)
C2—C5—H5	114.2	C26—C25—H25	119.2
C7—C6—C11	119.3 (3)	C24—C25—H25	119.2
C7—C6—N1	120.0 (2)	C27—C26—C25	119.6 (5)
C11—C6—N1	120.7 (2)	C27—C26—H26	120.2
C6—C7—C8	121.0 (3)	C25—C26—H26	120.2
C6—C7—H7	119.5	C26—C27—C28	121.2 (4)
C8—C7—H7	119.5	C26—C27—Cl1	120.3 (5)
C9—C8—C7	119.6 (3)	C28—C27—Cl1	118.5 (4)
C9—C8—H8	120.2	C27—C28—C29	120.1 (4)
C7—C8—H8	120.2	C27—C28—H28	120.0
O3—C9—C10	116.0 (3)	C29—C28—H28	120.0
O3—C9—C8	124.6 (3)	C24—C29—C28	119.5 (4)
C10—C9—C8	119.4 (3)	C24—C29—H29	120.2
C9—C10—C11	121.3 (3)	C28—C29—H29	120.2
C9—C10—H10	119.4	C3—C30—Se1	110.4 (2)
C11—C10—H10	119.4	C3—C30—H30A	109.6
C10—C11—C6	119.5 (3)	Se1—C30—H30A	109.6
C10—C11—H11	120.2	C3—C30—H30B	109.6
C6—C11—H11	120.2	Se1—C30—H30B	109.6
O3—C12—H12A	109.5	H30A—C30—H30B	108.1
O3—C12—H12B	109.5	C32—C31—C36	117.1 (3)
H12A—C12—H12B	109.5	C32—C31—Se1	123.3 (3)
O3—C12—H12C	109.5	C36—C31—Se1	119.6 (3)
H12A—C12—H12C	109.5	C31—C32—C33	120.7 (4)
H12B—C12—H12C	109.5	C31—C32—H32	119.6
O1—C13—C22	107.84 (19)	C33—C32—H32	119.6
O1—C13—C14	104.49 (19)	C34—C33—C32	121.1 (4)
C22—C13—C14	110.4 (2)	C34—C33—H33	119.4
O1—C13—C23	105.42 (18)	C32—C33—H33	119.4
C22—C13—C23	114.9 (2)	C33—C34—C35	120.0 (4)
C14—C13—C23	112.90 (19)	C33—C34—H34	120.0
O2—C14—C15	121.9 (2)	C35—C34—H34	120.0
O2—C14—C13	121.2 (2)	C34—C35—C36	120.9 (4)
C15—C14—C13	116.9 (2)	C34—C35—H35	119.6
C20—C15—C16	119.1 (2)	C36—C35—H35	119.6
C20—C15—C14	121.6 (2)	C31—C36—C35	120.2 (4)
C16—C15—C14	119.3 (2)	C31—C36—H36	119.9
C17—C16—C15	119.4 (3)	C35—C36—H36	119.9
C17—C16—H16	120.3	C1—N1—C6	134.1 (2)
C15—C16—H16	120.3	C1—N1—C5	94.9 (2)
C18—C17—C16	120.9 (3)	C6—N1—C5	130.8 (2)
C18—C17—H17	119.6	O1—N2—C4	105.64 (18)
C16—C17—H17	119.6	O1—N2—C3	110.5 (2)
C19—C18—C17	120.5 (3)	C4—N2—C3	108.43 (19)
C19—C18—H18	119.8	N2—O1—C13	109.84 (17)
C17—C18—H18	119.8	C9—O3—C12	118.3 (3)
C18—C19—C20	120.5 (3)	C31—Se1—C30	97.81 (12)
C18—C19—H19	119.8
O4—C1—C2—C3	−72.1 (4)	C14—C13—C23—C24	95.7 (3)
N1—C1—C2—C3	106.3 (3)	O1—C13—C23—C4	−23.4 (2)
O4—C1—C2—C5	−178.7 (3)	C22—C13—C23—C4	95.2 (2)
N1—C1—C2—C5	−0.26 (18)	C14—C13—C23—C4	−136.9 (2)
C1—C2—C3—N2	−116.6 (2)	C4—C23—C24—C25	143.3 (2)
C5—C2—C3—N2	−22.8 (2)	C13—C23—C24—C25	−96.9 (3)
C1—C2—C3—C30	126.5 (3)	C4—C23—C24—C29	−35.4 (4)
C5—C2—C3—C30	−139.6 (3)	C13—C23—C24—C29	84.4 (3)
N2—C4—C5—N1	117.0 (2)	C29—C24—C25—C26	−0.4 (4)
C23—C4—C5—N1	3.3 (4)	C23—C24—C25—C26	−179.1 (3)
N2—C4—C5—C2	21.6 (2)	C24—C25—C26—C27	0.6 (5)
C23—C4—C5—C2	−92.1 (3)	C25—C26—C27—C28	−0.6 (6)
C1—C2—C5—N1	0.25 (17)	C25—C26—C27—Cl1	177.2 (3)
C3—C2—C5—N1	−117.0 (2)	C26—C27—C28—C29	0.4 (6)
C1—C2—C5—C4	118.3 (2)	Cl1—C27—C28—C29	−177.5 (3)
C3—C2—C5—C4	1.0 (3)	C25—C24—C29—C28	0.2 (5)
C11—C6—C7—C8	1.1 (4)	C23—C24—C29—C28	178.9 (3)
N1—C6—C7—C8	−177.1 (3)	C27—C28—C29—C24	−0.2 (6)
C6—C7—C8—C9	−0.3 (5)	N2—C3—C30—Se1	−172.35 (18)
C7—C8—C9—O3	−179.8 (3)	C2—C3—C30—Se1	−59.6 (3)
C7—C8—C9—C10	−1.2 (5)	C36—C31—C32—C33	0.3 (6)
O3—C9—C10—C11	−179.4 (3)	Se1—C31—C32—C33	−178.8 (3)
C8—C9—C10—C11	1.9 (5)	C31—C32—C33—C34	0.0 (7)
C9—C10—C11—C6	−1.1 (5)	C32—C33—C34—C35	−0.8 (7)
C7—C6—C11—C10	−0.4 (4)	C33—C34—C35—C36	1.4 (7)
N1—C6—C11—C10	177.7 (3)	C32—C31—C36—C35	0.3 (5)
O1—C13—C14—O2	−96.4 (3)	Se1—C31—C36—C35	179.4 (3)
C22—C13—C14—O2	147.9 (3)	C34—C35—C36—C31	−1.1 (7)
C23—C13—C14—O2	17.7 (4)	O4—C1—N1—C6	−5.6 (5)
O1—C13—C14—C15	80.9 (2)	C2—C1—N1—C6	176.0 (3)
C22—C13—C14—C15	−34.9 (3)	O4—C1—N1—C5	178.7 (3)
C23—C13—C14—C15	−165.1 (2)	C2—C1—N1—C5	0.28 (19)
O2—C14—C15—C20	−176.3 (3)	C7—C6—N1—C1	−162.9 (3)
C13—C14—C15—C20	6.5 (3)	C11—C6—N1—C1	19.0 (4)
O2—C14—C15—C16	3.8 (4)	C7—C6—N1—C5	11.4 (4)
C13—C14—C15—C16	−173.4 (2)	C11—C6—N1—C5	−166.7 (2)
C20—C15—C16—C17	−0.7 (4)	C4—C5—N1—C1	−106.8 (3)
C14—C15—C16—C17	179.3 (3)	C2—C5—N1—C1	−0.28 (19)
C15—C16—C17—C18	1.0 (5)	C4—C5—N1—C6	77.3 (3)
C16—C17—C18—C19	−0.3 (5)	C2—C5—N1—C6	−176.2 (2)
C17—C18—C19—C20	−0.8 (5)	C23—C4—N2—O1	−33.7 (2)
C16—C15—C20—C19	−0.4 (4)	C5—C4—N2—O1	−156.62 (19)
C14—C15—C20—C19	179.7 (2)	C23—C4—N2—C3	84.8 (2)
C16—C15—C20—C21	−179.8 (3)	C5—C4—N2—C3	−38.1 (2)
C14—C15—C20—C21	0.3 (4)	C30—C3—N2—O1	−84.9 (3)
C18—C19—C20—C15	1.1 (4)	C2—C3—N2—O1	153.83 (18)
C18—C19—C20—C21	−179.5 (3)	C30—C3—N2—C4	159.7 (2)
C15—C20—C21—C22	22.0 (4)	C2—C3—N2—C4	38.5 (2)
C19—C20—C21—C22	−157.4 (3)	C4—N2—O1—C13	18.9 (2)
O1—C13—C22—C21	−56.5 (3)	C3—N2—O1—C13	−98.2 (2)
C14—C13—C22—C21	57.1 (3)	C22—C13—O1—N2	−119.7 (2)
C23—C13—C22—C21	−173.8 (2)	C14—C13—O1—N2	122.8 (2)
C20—C21—C22—C13	−50.9 (3)	C23—C13—O1—N2	3.6 (2)
N2—C4—C23—C24	161.9 (2)	C10—C9—O3—C12	173.6 (3)
C5—C4—C23—C24	−85.5 (3)	C8—C9—O3—C12	−7.8 (5)
N2—C4—C23—C13	34.9 (2)	C32—C31—Se1—C30	−48.0 (3)
C5—C4—C23—C13	147.6 (2)	C36—C31—Se1—C30	132.9 (3)
O1—C13—C23—C24	−150.9 (2)	C3—C30—Se1—C31	175.9 (2)
C22—C13—C23—C24	−32.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4i	0.98	2.57	3.305 (3)	132
C23—H23···O2	0.98	2.32	2.803 (3)	109
C23—H23···N1	0.98	2.54	2.918 (3)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4i	0.98	2.57	3.305 (3)	132
C23—H23⋯O2	0.98	2.32	2.803 (3)	109
C23—H23⋯N1	0.98	2.54	2.918 (3)	103

Symmetry code: (i) .