Ethyl 1''-benzyl-1'-methyl-2''-oxodi-spiro-[indeno-[1,2-b]quinoxaline-11,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate.

In the title compound, C36H30N4O3, the quinoxaline-indene system is roughly planar, with a maximum deviation from the mean plane of 0.218 Å for the C atom shared with the central pyrrolidine ring. This latter ring forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline-indene system and the indole ring, respectively. The central pyrrolidine ring has an envelope conformation with the N atom as the flap, while the pyrrolidine and five-membered rings of the indole group adopt twisted conformation and envelope (with the C atom bearing the quinoxaline-indene system as the flap) conformations, respectively. In the crystal, mol-ecules are linked via weak C-H⋯N hydrogen bonds, forming a chain running along [100].

Related literature

For details of the synthesis, see: Azizian et al. (2005 ▶). For uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003 ▶); Zarranz et al. (2003 ▶). For a related structure, see: Srinivasan et al. (2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C36H30N4O3

M = 566.64

Triclinic,

a = 11.1927 (2) Å

b = 11.4535 (3) Å

c = 12.1206 (3) Å

α = 87.637 (2)°

β = 86.048 (1)°

γ = 70.564 (2)°

V = 1461.50 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.971, T max = 0.980

21785 measured reflections

5987 independent reflections

4956 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 1.04

5987 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.28 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 for Windows (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/S1600536813011525/bg2503sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011525/bg2503Isup2.hkl

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

C36H30N4O3	Z = 2
Mr = 566.64	F(000) = 596
Triclinic, P1	Dx = 1.288 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1927 (2) Å	Cell parameters from 5987 reflections
b = 11.4535 (3) Å	θ = 1.7–26.4°
c = 12.1206 (3) Å	µ = 0.08 mm−1
α = 87.637 (2)°	T = 293 K
β = 86.048 (1)°	Block, colourless
γ = 70.564 (2)°	0.35 × 0.30 × 0.25 mm
V = 1461.50 (6) Å3

Bruker APEXII CCD area detector diffractometer	5987 independent reflections
Radiation source: fine-focus sealed tube	4956 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.971, Tmax = 0.980	k = −14→14
21785 measured reflections	l = −15→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.3957P] where P = (Fo2 + 2Fc2)/3
5987 reflections	(Δ/σ)max < 0.001
388 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.46495 (16)	0.33734 (15)	0.47540 (12)	0.0467 (4)
C2	0.58578 (19)	0.2802 (2)	0.51621 (16)	0.0655 (5)
H2	0.6504	0.2270	0.4717	0.079*
C3	0.6081 (2)	0.3030 (2)	0.62131 (18)	0.0796 (6)
H3	0.6886	0.2662	0.6475	0.096*
C4	0.5112 (2)	0.3814 (2)	0.69003 (17)	0.0813 (7)
H4	0.5276	0.3952	0.7617	0.098*
C5	0.3943 (2)	0.4369 (2)	0.65289 (15)	0.0716 (6)
H5	0.3306	0.4882	0.6994	0.086*
C6	0.36772 (17)	0.41794 (15)	0.54397 (13)	0.0505 (4)
C7	0.32937 (13)	0.36757 (13)	0.33956 (11)	0.0355 (3)
C8	0.23311 (15)	0.45322 (13)	0.40719 (11)	0.0401 (3)
C9	0.12264 (14)	0.50836 (13)	0.34192 (12)	0.0416 (3)
C10	0.00864 (17)	0.59934 (16)	0.36960 (14)	0.0573 (4)
H10	−0.0093	0.6301	0.4409	0.069*
C11	−0.07808 (18)	0.64365 (17)	0.28945 (16)	0.0629 (5)
H11	−0.1557	0.7039	0.3070	0.076*
C12	−0.05019 (17)	0.59895 (16)	0.18324 (15)	0.0549 (4)
H12	−0.1084	0.6315	0.1295	0.066*
C13	0.06289 (15)	0.50652 (14)	0.15560 (13)	0.0451 (3)
H13	0.0803	0.4767	0.0840	0.054*
C14	0.15026 (13)	0.45856 (12)	0.23576 (11)	0.0373 (3)
C15	0.27707 (13)	0.35239 (12)	0.23015 (11)	0.0345 (3)
C16	0.25846 (13)	0.21964 (13)	0.22938 (11)	0.0362 (3)
C17	0.13440 (14)	0.23436 (13)	0.17136 (12)	0.0396 (3)
C18	0.22998 (15)	0.16963 (13)	0.34140 (11)	0.0398 (3)
C19	0.30797 (18)	0.11634 (15)	0.42594 (13)	0.0519 (4)
H19	0.3939	0.1070	0.4190	0.062*
C20	0.2559 (2)	0.07688 (18)	0.52142 (15)	0.0671 (5)
H20	0.3072	0.0415	0.5794	0.081*
C21	0.1297 (2)	0.08966 (19)	0.53107 (15)	0.0697 (6)
H21	0.0964	0.0642	0.5965	0.084*
C22	0.0499 (2)	0.13956 (17)	0.44591 (15)	0.0597 (5)
H22	−0.0355	0.1465	0.4524	0.072*
C23	0.10286 (15)	0.17842 (13)	0.35109 (12)	0.0430 (3)
C24	−0.08781 (15)	0.25705 (16)	0.23371 (16)	0.0538 (4)
H24A	−0.1076	0.3166	0.1727	0.065*
H24B	−0.1353	0.2980	0.2993	0.065*
C25	−0.13298 (14)	0.15082 (14)	0.20920 (12)	0.0429 (3)
C26	−0.25876 (15)	0.16256 (17)	0.23242 (13)	0.0505 (4)
H26	−0.3132	0.2341	0.2656	0.061*
C27	−0.30515 (17)	0.0699 (2)	0.20724 (15)	0.0612 (5)
H27	−0.3901	0.0790	0.2237	0.073*
C28	−0.2258 (2)	−0.0355 (2)	0.15803 (16)	0.0653 (5)
H28	−0.2569	−0.0980	0.1409	0.078*
C29	−0.1006 (2)	−0.04890 (18)	0.13409 (17)	0.0645 (5)
H29	−0.0470	−0.1204	0.1004	0.077*
C30	−0.05354 (16)	0.04371 (16)	0.15982 (15)	0.0551 (4)
H30	0.0317	0.0338	0.1439	0.066*
C31	0.2604 (3)	0.7740 (2)	0.0863 (2)	0.0978 (8)
H31A	0.2272	0.8468	0.0407	0.147*
H31B	0.3403	0.7718	0.1123	0.147*
H31C	0.2018	0.7759	0.1484	0.147*
C32	0.2783 (3)	0.6663 (2)	0.02305 (18)	0.0802 (7)
H32A	0.3364	0.6647	−0.0405	0.096*
H32B	0.1979	0.6682	−0.0036	0.096*
C33	0.33704 (16)	0.44973 (16)	0.04707 (12)	0.0481 (4)
C34	0.37562 (14)	0.34434 (14)	0.12994 (11)	0.0402 (3)
H34	0.4544	0.3451	0.1601	0.048*
C35	0.40247 (16)	0.21799 (15)	0.08010 (13)	0.0488 (4)
H35A	0.3479	0.2227	0.0201	0.059*
H35B	0.4903	0.1840	0.0526	0.059*
C36	0.37646 (19)	0.02159 (16)	0.14274 (16)	0.0613 (5)
H36A	0.4566	−0.0218	0.1055	0.092*
H36B	0.3094	0.0299	0.0946	0.092*
H36C	0.3645	−0.0239	0.2084	0.092*
N1	0.44398 (12)	0.31244 (12)	0.36901 (10)	0.0431 (3)
N2	0.24881 (14)	0.47965 (13)	0.50795 (11)	0.0516 (3)
N3	0.04620 (12)	0.22332 (12)	0.25098 (11)	0.0445 (3)
N4	0.37489 (12)	0.14388 (11)	0.17259 (10)	0.0438 (3)
O1	0.11649 (12)	0.25347 (11)	0.07356 (9)	0.0526 (3)
O2	0.32960 (13)	0.55571 (11)	0.09209 (9)	0.0587 (3)
O3	0.31436 (17)	0.44125 (14)	−0.04700 (10)	0.0807 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0535 (9)	0.0549 (9)	0.0381 (8)	−0.0249 (7)	−0.0133 (7)	0.0024 (7)
C2	0.0579 (11)	0.0865 (14)	0.0518 (10)	−0.0209 (10)	−0.0190 (8)	0.0026 (9)
C3	0.0773 (14)	0.1032 (17)	0.0632 (12)	−0.0309 (13)	−0.0386 (11)	0.0092 (12)
C4	0.1098 (18)	0.0864 (15)	0.0518 (11)	−0.0305 (13)	−0.0403 (12)	−0.0051 (10)
C5	0.0979 (16)	0.0701 (12)	0.0437 (10)	−0.0186 (11)	−0.0255 (10)	−0.0102 (9)
C6	0.0674 (11)	0.0508 (9)	0.0373 (8)	−0.0222 (8)	−0.0147 (7)	−0.0029 (7)
C7	0.0425 (8)	0.0384 (7)	0.0302 (6)	−0.0190 (6)	−0.0046 (5)	−0.0007 (5)
C8	0.0500 (8)	0.0402 (7)	0.0325 (7)	−0.0174 (6)	−0.0038 (6)	−0.0039 (6)
C9	0.0474 (8)	0.0398 (7)	0.0374 (7)	−0.0137 (6)	−0.0045 (6)	−0.0018 (6)
C10	0.0597 (11)	0.0547 (10)	0.0469 (9)	−0.0041 (8)	−0.0011 (8)	−0.0097 (7)
C11	0.0549 (10)	0.0562 (10)	0.0630 (11)	0.0021 (8)	−0.0072 (8)	−0.0030 (8)
C12	0.0526 (10)	0.0512 (9)	0.0565 (10)	−0.0093 (7)	−0.0183 (8)	0.0064 (7)
C13	0.0514 (9)	0.0459 (8)	0.0395 (8)	−0.0168 (7)	−0.0114 (7)	0.0018 (6)
C14	0.0423 (8)	0.0365 (7)	0.0356 (7)	−0.0159 (6)	−0.0051 (6)	0.0000 (5)
C15	0.0395 (7)	0.0383 (7)	0.0287 (6)	−0.0162 (6)	−0.0047 (5)	−0.0007 (5)
C16	0.0428 (8)	0.0379 (7)	0.0303 (6)	−0.0160 (6)	−0.0054 (6)	−0.0017 (5)
C17	0.0481 (8)	0.0393 (7)	0.0363 (7)	−0.0196 (6)	−0.0082 (6)	−0.0029 (6)
C18	0.0526 (9)	0.0355 (7)	0.0348 (7)	−0.0188 (6)	−0.0050 (6)	−0.0007 (5)
C19	0.0680 (11)	0.0472 (8)	0.0447 (9)	−0.0231 (8)	−0.0167 (8)	0.0081 (7)
C20	0.1049 (17)	0.0611 (11)	0.0441 (9)	−0.0379 (11)	−0.0202 (10)	0.0159 (8)
C21	0.1144 (18)	0.0666 (12)	0.0388 (9)	−0.0469 (12)	0.0051 (10)	0.0062 (8)
C22	0.0739 (12)	0.0631 (11)	0.0516 (10)	−0.0381 (9)	0.0122 (9)	−0.0067 (8)
C23	0.0560 (9)	0.0389 (7)	0.0383 (8)	−0.0212 (7)	−0.0004 (6)	−0.0047 (6)
C24	0.0418 (9)	0.0488 (9)	0.0697 (11)	−0.0120 (7)	−0.0065 (8)	−0.0077 (8)
C25	0.0386 (8)	0.0508 (8)	0.0404 (8)	−0.0163 (6)	−0.0052 (6)	0.0018 (6)
C26	0.0395 (8)	0.0666 (10)	0.0439 (8)	−0.0163 (7)	−0.0052 (6)	0.0082 (7)
C27	0.0486 (10)	0.0891 (14)	0.0572 (10)	−0.0384 (10)	−0.0167 (8)	0.0245 (10)
C28	0.0812 (14)	0.0735 (12)	0.0610 (11)	−0.0502 (11)	−0.0256 (10)	0.0169 (10)
C29	0.0744 (13)	0.0559 (10)	0.0683 (12)	−0.0273 (9)	−0.0049 (10)	−0.0083 (9)
C30	0.0450 (9)	0.0555 (9)	0.0671 (11)	−0.0199 (7)	0.0023 (8)	−0.0081 (8)
C31	0.139 (2)	0.0601 (13)	0.0865 (17)	−0.0203 (14)	−0.0283 (16)	0.0143 (12)
C32	0.124 (2)	0.0633 (12)	0.0583 (12)	−0.0387 (13)	−0.0150 (12)	0.0239 (10)
C33	0.0567 (10)	0.0596 (9)	0.0328 (7)	−0.0262 (8)	−0.0013 (6)	0.0016 (7)
C34	0.0431 (8)	0.0499 (8)	0.0313 (7)	−0.0204 (6)	−0.0014 (6)	−0.0024 (6)
C35	0.0544 (9)	0.0547 (9)	0.0387 (8)	−0.0206 (7)	0.0062 (7)	−0.0096 (7)
C36	0.0738 (12)	0.0445 (9)	0.0654 (11)	−0.0188 (8)	0.0016 (9)	−0.0164 (8)
N1	0.0431 (7)	0.0525 (7)	0.0361 (6)	−0.0181 (6)	−0.0076 (5)	−0.0014 (5)
N2	0.0643 (9)	0.0524 (8)	0.0358 (7)	−0.0144 (7)	−0.0091 (6)	−0.0082 (6)
N3	0.0431 (7)	0.0494 (7)	0.0458 (7)	−0.0210 (6)	−0.0059 (5)	−0.0015 (5)
N4	0.0477 (7)	0.0404 (6)	0.0431 (7)	−0.0139 (5)	0.0012 (5)	−0.0092 (5)
O1	0.0673 (7)	0.0607 (7)	0.0368 (6)	−0.0282 (6)	−0.0168 (5)	0.0008 (5)
O2	0.0900 (9)	0.0532 (7)	0.0422 (6)	−0.0356 (6)	−0.0133 (6)	0.0103 (5)
O3	0.1283 (13)	0.0852 (10)	0.0349 (6)	−0.0421 (9)	−0.0181 (7)	0.0060 (6)

C1—N1	1.3842 (19)	C20—H20	0.9300
C1—C2	1.407 (2)	C21—C22	1.388 (3)
C1—C6	1.413 (2)	C21—H21	0.9300
C2—C3	1.367 (3)	C22—C23	1.382 (2)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.402 (3)	C23—N3	1.406 (2)
C3—H3	0.9300	C24—N3	1.447 (2)
C4—C5	1.351 (3)	C24—C25	1.511 (2)
C4—H4	0.9300	C24—H24A	0.9700
C5—C6	1.414 (2)	C24—H24B	0.9700
C5—H5	0.9300	C25—C26	1.379 (2)
C6—N2	1.375 (2)	C25—C30	1.384 (2)
C7—N1	1.2950 (19)	C26—C27	1.380 (3)
C7—C8	1.427 (2)	C26—H26	0.9300
C7—C15	1.5249 (17)	C27—C28	1.370 (3)
C8—N2	1.3075 (18)	C27—H27	0.9300
C8—C9	1.459 (2)	C28—C29	1.369 (3)
C9—C10	1.383 (2)	C28—H28	0.9300
C9—C14	1.402 (2)	C29—C30	1.387 (2)
C10—C11	1.380 (3)	C29—H29	0.9300
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.382 (3)	C31—C32	1.430 (3)
C11—H11	0.9300	C31—H31A	0.9600
C12—C13	1.383 (2)	C31—H31B	0.9600
C12—H12	0.9300	C31—H31C	0.9600
C13—C14	1.390 (2)	C32—O2	1.459 (2)
C13—H13	0.9300	C32—H32A	0.9700
C14—C15	1.5306 (19)	C32—H32B	0.9700
C15—C34	1.5677 (19)	C33—O3	1.1997 (19)
C15—C16	1.6023 (18)	C33—O2	1.326 (2)
C16—N4	1.4485 (19)	C33—C34	1.505 (2)
C16—C18	1.5069 (19)	C34—C35	1.519 (2)
C16—C17	1.5556 (19)	C34—H34	0.9800
C17—O1	1.2146 (17)	C35—N4	1.456 (2)
C17—N3	1.3651 (19)	C35—H35A	0.9700
C18—C19	1.379 (2)	C35—H35B	0.9700
C18—C23	1.390 (2)	C36—N4	1.455 (2)
C19—C20	1.386 (3)	C36—H36A	0.9600
C19—H19	0.9300	C36—H36B	0.9600
C20—C21	1.369 (3)	C36—H36C	0.9600
N1—C1—C2	119.04 (16)	C21—C22—H22	121.4
N1—C1—C6	121.56 (14)	C22—C23—C18	121.71 (15)
C2—C1—C6	119.40 (15)	C22—C23—N3	128.49 (16)
C3—C2—C1	119.9 (2)	C18—C23—N3	109.68 (13)
C3—C2—H2	120.0	N3—C24—C25	115.36 (13)
C1—C2—H2	120.0	N3—C24—H24A	108.4
C2—C3—C4	120.76 (19)	C25—C24—H24A	108.4
C2—C3—H3	119.6	N3—C24—H24B	108.4
C4—C3—H3	119.6	C25—C24—H24B	108.4
C5—C4—C3	120.43 (17)	H24A—C24—H24B	107.5
C5—C4—H4	119.8	C26—C25—C30	118.58 (15)
C3—C4—H4	119.8	C26—C25—C24	119.15 (15)
C4—C5—C6	120.7 (2)	C30—C25—C24	122.21 (14)
C4—C5—H5	119.7	C25—C26—C27	121.06 (17)
C6—C5—H5	119.7	C25—C26—H26	119.5
N2—C6—C1	122.27 (13)	C27—C26—H26	119.5
N2—C6—C5	118.93 (17)	C28—C27—C26	119.89 (16)
C1—C6—C5	118.79 (16)	C28—C27—H27	120.1
N1—C7—C8	123.68 (13)	C26—C27—H27	120.1
N1—C7—C15	126.17 (13)	C29—C28—C27	119.96 (17)
C8—C7—C15	110.16 (12)	C29—C28—H28	120.0
N2—C8—C7	123.74 (14)	C27—C28—H28	120.0
N2—C8—C9	127.91 (14)	C28—C29—C30	120.32 (18)
C7—C8—C9	108.24 (12)	C28—C29—H29	119.8
C10—C9—C14	121.55 (14)	C30—C29—H29	119.8
C10—C9—C8	129.74 (14)	C25—C30—C29	120.19 (16)
C14—C9—C8	108.63 (13)	C25—C30—H30	119.9
C11—C10—C9	118.74 (16)	C29—C30—H30	119.9
C11—C10—H10	120.6	C32—C31—H31A	109.5
C9—C10—H10	120.6	C32—C31—H31B	109.5
C10—C11—C12	120.38 (16)	H31A—C31—H31B	109.5
C10—C11—H11	119.8	C32—C31—H31C	109.5
C12—C11—H11	119.8	H31A—C31—H31C	109.5
C11—C12—C13	121.07 (15)	H31B—C31—H31C	109.5
C11—C12—H12	119.5	C31—C32—O2	109.46 (18)
C13—C12—H12	119.5	C31—C32—H32A	109.8
C12—C13—C14	119.45 (14)	O2—C32—H32A	109.8
C12—C13—H13	120.3	C31—C32—H32B	109.8
C14—C13—H13	120.3	O2—C32—H32B	109.8
C13—C14—C9	118.73 (14)	H32A—C32—H32B	108.2
C13—C14—C15	130.38 (13)	O3—C33—O2	123.62 (16)
C9—C14—C15	110.87 (12)	O3—C33—C34	125.49 (16)
C7—C15—C14	100.73 (11)	O2—C33—C34	110.89 (12)
C7—C15—C34	112.04 (11)	C33—C34—C35	113.57 (12)
C14—C15—C34	120.22 (11)	C33—C34—C15	114.86 (12)
C7—C15—C16	109.35 (10)	C35—C34—C15	106.14 (11)
C14—C15—C16	112.16 (11)	C33—C34—H34	107.3
C34—C15—C16	102.35 (10)	C35—C34—H34	107.3
N4—C16—C18	114.48 (12)	C15—C34—H34	107.3
N4—C16—C17	115.63 (11)	N4—C35—C34	103.40 (11)
C18—C16—C17	101.08 (11)	N4—C35—H35A	111.1
N4—C16—C15	102.63 (11)	C34—C35—H35A	111.1
C18—C16—C15	115.02 (11)	N4—C35—H35B	111.1
C17—C16—C15	108.36 (11)	C34—C35—H35B	111.1
O1—C17—N3	125.16 (14)	H35A—C35—H35B	109.0
O1—C17—C16	127.30 (14)	N4—C36—H36A	109.5
N3—C17—C16	107.53 (11)	N4—C36—H36B	109.5
C19—C18—C23	119.96 (14)	H36A—C36—H36B	109.5
C19—C18—C16	130.95 (15)	N4—C36—H36C	109.5
C23—C18—C16	109.03 (12)	H36A—C36—H36C	109.5
C18—C19—C20	118.79 (17)	H36B—C36—H36C	109.5
C18—C19—H19	120.6	C7—N1—C1	114.53 (13)
C20—C19—H19	120.6	C8—N2—C6	114.07 (14)
C21—C20—C19	120.53 (17)	C17—N3—C23	110.92 (12)
C21—C20—H20	119.7	C17—N3—C24	123.73 (13)
C19—C20—H20	119.7	C23—N3—C24	125.33 (14)
C20—C21—C22	121.83 (17)	C16—N4—C36	115.10 (13)
C20—C21—H21	119.1	C16—N4—C35	107.01 (12)
C22—C21—H21	119.1	C36—N4—C35	114.35 (13)
C23—C22—C21	117.12 (18)	C33—O2—C32	115.43 (14)
C23—C22—H22	121.4
N1—C1—C2—C3	−179.60 (18)	C23—C18—C19—C20	−2.6 (2)
C6—C1—C2—C3	0.0 (3)	C16—C18—C19—C20	−179.42 (15)
C1—C2—C3—C4	1.1 (4)	C18—C19—C20—C21	0.6 (3)
C2—C3—C4—C5	−0.8 (4)	C19—C20—C21—C22	1.4 (3)
C3—C4—C5—C6	−0.5 (4)	C20—C21—C22—C23	−1.3 (3)
N1—C1—C6—N2	−2.5 (3)	C21—C22—C23—C18	−0.8 (2)
C2—C1—C6—N2	177.92 (16)	C21—C22—C23—N3	174.94 (16)
N1—C1—C6—C5	178.32 (17)	C19—C18—C23—C22	2.7 (2)
C2—C1—C6—C5	−1.2 (3)	C16—C18—C23—C22	−179.78 (14)
C4—C5—C6—N2	−177.67 (19)	C19—C18—C23—N3	−173.72 (13)
C4—C5—C6—C1	1.5 (3)	C16—C18—C23—N3	3.76 (16)
N1—C7—C8—N2	−3.8 (2)	N3—C24—C25—C26	155.66 (15)
C15—C7—C8—N2	176.38 (14)	N3—C24—C25—C30	−27.1 (2)
N1—C7—C8—C9	172.61 (13)	C30—C25—C26—C27	0.0 (2)
C15—C7—C8—C9	−7.16 (16)	C24—C25—C26—C27	177.35 (15)
N2—C8—C9—C10	−0.8 (3)	C25—C26—C27—C28	−0.2 (2)
C7—C8—C9—C10	−177.05 (17)	C26—C27—C28—C29	0.1 (3)
N2—C8—C9—C14	175.83 (15)	C27—C28—C29—C30	0.2 (3)
C7—C8—C9—C14	−0.44 (16)	C26—C25—C30—C29	0.3 (3)
C14—C9—C10—C11	−1.6 (3)	C24—C25—C30—C29	−176.91 (17)
C8—C9—C10—C11	174.65 (17)	C28—C29—C30—C25	−0.5 (3)
C9—C10—C11—C12	−1.0 (3)	O3—C33—C34—C35	8.2 (2)
C10—C11—C12—C13	2.0 (3)	O2—C33—C34—C35	−172.55 (14)
C11—C12—C13—C14	−0.5 (3)	O3—C33—C34—C15	−114.25 (19)
C12—C13—C14—C9	−2.0 (2)	O2—C33—C34—C15	65.02 (17)
C12—C13—C14—C15	175.86 (15)	C7—C15—C34—C33	−115.27 (14)
C10—C9—C14—C13	3.1 (2)	C14—C15—C34—C33	2.65 (18)
C8—C9—C14—C13	−173.87 (13)	C16—C15—C34—C33	127.70 (12)
C10—C9—C14—C15	−175.17 (15)	C7—C15—C34—C35	118.37 (13)
C8—C9—C14—C15	7.88 (16)	C14—C15—C34—C35	−123.71 (13)
N1—C7—C15—C14	−168.74 (13)	C16—C15—C34—C35	1.34 (14)
C8—C7—C15—C14	11.03 (14)	C33—C34—C35—N4	−152.74 (13)
N1—C7—C15—C34	−39.74 (19)	C15—C34—C35—N4	−25.61 (15)
C8—C7—C15—C34	140.03 (12)	C8—C7—N1—C1	3.7 (2)
N1—C7—C15—C16	73.01 (17)	C15—C7—N1—C1	−176.57 (13)
C8—C7—C15—C16	−107.22 (13)	C2—C1—N1—C7	178.85 (15)
C13—C14—C15—C7	170.60 (14)	C6—C1—N1—C7	−0.7 (2)
C9—C14—C15—C7	−11.42 (14)	C7—C8—N2—C6	0.4 (2)
C13—C14—C15—C34	47.1 (2)	C9—C8—N2—C6	−175.31 (15)
C9—C14—C15—C34	−134.95 (13)	C1—C6—N2—C8	2.5 (2)
C13—C14—C15—C16	−73.22 (18)	C5—C6—N2—C8	−178.34 (16)
C9—C14—C15—C16	104.77 (13)	O1—C17—N3—C23	168.75 (14)
C7—C15—C16—N4	−95.51 (12)	C16—C17—N3—C23	−11.93 (15)
C14—C15—C16—N4	153.63 (11)	O1—C17—N3—C24	−12.8 (2)
C34—C15—C16—N4	23.44 (13)	C16—C17—N3—C24	166.53 (13)
C7—C15—C16—C18	29.47 (16)	C22—C23—N3—C17	−170.70 (15)
C14—C15—C16—C18	−81.39 (14)	C18—C23—N3—C17	5.45 (16)
C34—C15—C16—C18	148.41 (12)	C22—C23—N3—C24	10.9 (2)
C7—C15—C16—C17	141.70 (12)	C18—C23—N3—C24	−172.98 (13)
C14—C15—C16—C17	30.85 (15)	C25—C24—N3—C17	98.76 (18)
C34—C15—C16—C17	−99.35 (12)	C25—C24—N3—C23	−83.00 (19)
N4—C16—C17—O1	−43.3 (2)	C18—C16—N4—C36	64.59 (17)
C18—C16—C17—O1	−167.54 (14)	C17—C16—N4—C36	−52.33 (18)
C15—C16—C17—O1	71.18 (18)	C15—C16—N4—C36	−170.08 (13)
N4—C16—C17—N3	137.37 (12)	C18—C16—N4—C35	−167.14 (12)
C18—C16—C17—N3	13.15 (14)	C17—C16—N4—C35	75.94 (15)
C15—C16—C17—N3	−108.12 (12)	C15—C16—N4—C35	−41.81 (13)
N4—C16—C18—C19	42.1 (2)	C34—C35—N4—C16	43.20 (15)
C17—C16—C18—C19	167.08 (15)	C34—C35—N4—C36	171.90 (13)
C15—C16—C18—C19	−76.45 (19)	O3—C33—O2—C32	6.3 (3)
N4—C16—C18—C23	−135.02 (13)	C34—C33—O2—C32	−172.97 (16)
C17—C16—C18—C23	−10.03 (14)	C31—C32—O2—C33	172.6 (2)
C15—C16—C18—C23	106.44 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N4i	0.93	2.60	3.446 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯N4i	0.93	2.60	3.446 (2)	152

Symmetry code: (i) .