Ethyl 1-(4-methoxy-phen-yl)-2-nitro-3-[4-oxo-3-phenyl-1-(4-methoxy-phen-yl)azetidin-2-yl]-2,3,10,10a-tetra-hydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-carboxyl-ate.

In the mol-ecule of the title compound, C(38)H(37)N(3)O(7), the pyrrolidine ring adopts a twist conformation and the six-membered heterocyclic ring has a boat conformation. In the crystal structure, mol-ecules are linked into a three-dimensional framework through inter-molecular C-H⋯O hydrogen bonds. One ethyl group is disordered over two positions with occupancies 0.67 (2)/0.33 (2).

Related literature

For related literature, see: Allen et al. (1987 ▶); Amal Raj et al. (2003 ▶); Borthwick et al. (2003 ▶); Brakhage (1998 ▶); Cremer & Pople (1975 ▶); Fernandes et al. (2004 ▶); Kamala et al. (2008 ▶); Katritzky et al. (1996 ▶); Morin & Gorman (1982 ▶); Nardelli (1983 ▶); Sundari et al. (2006 ▶); Verkman (1990 ▶); Weissman et al. (1993 ▶); Georg & Ravikumar (1993 ▶); LaVoie et al. (1983 ▶).

Experimental

Crystal data

C38H37N3O7

M = 647.71

Orthorhombic,

a = 9.0149 (3) Å

b = 11.0865 (4) Å

c = 33.3731 (11) Å

V = 3335.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.982, T max = 0.982

68599 measured reflections

3960 independent reflections

3318 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.107

S = 1.05

3960 reflections

453 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP 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/S1600536808010428/bt2696sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010428/bt2696Isup2.hkl

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

C38H37N3O7	F000 = 1368
Mr = 647.71	Dx = 1.290 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 68599 reflections
a = 9.0149 (3) Å	θ = 1.2–26.7º
b = 11.0865 (4) Å	µ = 0.09 mm−1
c = 33.3731 (11) Å	T = 293 (2) K
V = 3335.4 (2) Å3	Prism, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker KappaAPEX2 diffractometer	3960 independent reflections
Radiation source: fine-focus sealed tube	3318 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 293(2) K	θmax = 26.7º
ω and φ scans	θmin = 1.2º
Absorption correction: multi-scan(Blessing, 1995)	h = −11→11
Tmin = 0.982, Tmax = 0.982	k = −13→13
68599 measured reflections	l = −42→42

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.4467P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.14 e Å−3
3960 reflections	Δρmin = −0.16 e Å−3
453 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: 0.0035 (7)
Secondary atom site location: difference Fourier map

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	Occ. (<1)
C1	0.5650 (3)	0.1895 (2)	0.11810 (7)	0.0428 (5)
H1	0.6078	0.1997	0.1449	0.051*
C2	0.6846 (3)	0.2110 (2)	0.08439 (7)	0.0465 (5)
H2	0.7811	0.2300	0.0964	0.056*
C3	0.6714 (3)	0.0759 (2)	0.07673 (7)	0.0518 (6)
C4	0.4217 (3)	0.26005 (18)	0.11375 (6)	0.0392 (5)
H4	0.3956	0.2613	0.0853	0.047*
C5	0.4352 (3)	0.3919 (2)	0.12799 (7)	0.0441 (5)
H5	0.4661	0.4435	0.1057	0.053*
C6	0.2805 (3)	0.4279 (2)	0.14202 (7)	0.0452 (5)
H6	0.2911	0.4792	0.1658	0.054*
C7	0.2091 (3)	0.3061 (2)	0.15540 (6)	0.0418 (5)
C8	0.0419 (3)	0.2946 (2)	0.14583 (8)	0.0509 (6)
H8A	−0.0144	0.3490	0.1628	0.061*
H8B	0.0240	0.3164	0.1181	0.061*
C9	−0.0065 (3)	0.1674 (2)	0.15306 (7)	0.0481 (6)
C10	−0.1225 (3)	0.1330 (3)	0.17775 (8)	0.0601 (7)
H10	−0.1790	0.1911	0.1908	0.072*
C11	−0.1538 (4)	0.0124 (3)	0.18292 (9)	0.0702 (8)
H11	−0.2323	−0.0106	0.1993	0.084*
C12	−0.0702 (4)	−0.0739 (3)	0.16414 (10)	0.0740 (9)
H12	−0.0926	−0.1551	0.1677	0.089*
C13	0.0469 (4)	−0.0409 (3)	0.13991 (9)	0.0645 (7)
H13	0.1039	−0.0996	0.1273	0.077*
C14	0.0792 (3)	0.0797 (2)	0.13448 (7)	0.0505 (6)
C15	0.2094 (3)	0.1248 (2)	0.11103 (7)	0.0480 (5)
H15A	0.2717	0.0576	0.1032	0.058*
H15B	0.1752	0.1650	0.0869	0.058*
C16	0.1960 (3)	0.4982 (2)	0.11054 (7)	0.0469 (5)
C17	0.0909 (3)	0.5824 (2)	0.12263 (8)	0.0601 (7)
H17	0.0744	0.5938	0.1499	0.072*
C18	0.0110 (4)	0.6489 (2)	0.09578 (9)	0.0658 (7)
H18	−0.0600	0.7033	0.1048	0.079*
C19	0.0358 (3)	0.6354 (2)	0.05499 (8)	0.0592 (7)
C20	0.1387 (3)	0.5535 (3)	0.04209 (8)	0.0598 (7)
H20	0.1563	0.5437	0.0148	0.072*
C21	0.2168 (3)	0.4850 (2)	0.06968 (7)	0.0550 (6)
H21	0.2852	0.4286	0.0605	0.066*
C22	0.6510 (3)	0.2965 (2)	0.05059 (7)	0.0484 (5)
C23	0.7102 (4)	0.4110 (3)	0.05080 (9)	0.0628 (7)
H23	0.7770	0.4333	0.0707	0.075*
C24	0.6704 (4)	0.4931 (3)	0.02139 (11)	0.0822 (10)
H24	0.7105	0.5704	0.0218	0.099*
C25	0.5729 (4)	0.4619 (3)	−0.00828 (10)	0.0822 (10)
H25	0.5448	0.5181	−0.0275	0.099*
C26	0.5175 (4)	0.3476 (3)	−0.00931 (8)	0.0732 (9)
H26	0.4531	0.3252	−0.0298	0.088*
C27	0.5563 (3)	0.2648 (3)	0.01987 (7)	0.0563 (6)
H27	0.5182	0.1869	0.0188	0.068*
C28	0.5268 (3)	−0.0417 (2)	0.12839 (7)	0.0471 (5)
C29	0.4518 (3)	−0.0313 (2)	0.16414 (8)	0.0549 (6)
H29	0.4239	0.0446	0.1733	0.066*
C30	0.4176 (3)	−0.1326 (2)	0.18659 (8)	0.0579 (7)
H30	0.3682	−0.1244	0.2109	0.069*
C31	0.4563 (4)	−0.2445 (2)	0.17306 (8)	0.0583 (7)
C32	0.5345 (4)	−0.2552 (2)	0.13739 (8)	0.0698 (8)
H32	0.5635	−0.3311	0.1286	0.084*
C33	0.5695 (4)	−0.1558 (2)	0.11504 (8)	0.0615 (7)
H33	0.6214	−0.1642	0.0911	0.074*
C34	0.3451 (6)	−0.3423 (3)	0.22891 (10)	0.1026 (15)
H34A	0.3317	−0.4215	0.2399	0.154*
H34B	0.2500	−0.3067	0.2236	0.154*
H34C	0.3984	−0.2930	0.2477	0.154*
C35	0.2155 (3)	0.2959 (2)	0.20132 (7)	0.0509 (6)
C36A	0.227 (2)	0.1693 (8)	0.2565 (2)	0.099 (4)	0.67 (2)
H36A	0.3178	0.1371	0.2677	0.119*	0.67 (2)
H36B	0.2132	0.2487	0.2681	0.119*	0.67 (2)
C36B	0.2763 (18)	0.166 (2)	0.2577 (7)	0.094 (8)	0.33 (2)
H36C	0.2370	0.2319	0.2737	0.113*	0.33 (2)
H36D	0.3801	0.1541	0.2641	0.113*	0.33 (2)
C37A	0.1243 (12)	0.1053 (17)	0.2693 (3)	0.113 (5)	0.67 (2)
H37A	0.1328	0.0977	0.2978	0.170*	0.67 (2)
H37B	0.1300	0.0269	0.2572	0.170*	0.67 (2)
H37C	0.0309	0.1419	0.2627	0.170*	0.67 (2)
C37B	0.182 (4)	0.0452 (14)	0.2633 (4)	0.130 (9)	0.33 (2)
H37D	0.1729	0.0272	0.2914	0.196*	0.33 (2)
H37E	0.2311	−0.0203	0.2500	0.196*	0.33 (2)
H37F	0.0849	0.0560	0.2520	0.196*	0.33 (2)
C38	−0.0228 (5)	0.6993 (3)	−0.01129 (10)	0.0934 (11)
H38A	−0.0871	0.7543	−0.0252	0.140*
H38B	−0.0431	0.6184	−0.0199	0.140*
H38C	0.0786	0.7190	−0.0171	0.140*
N1	0.5645 (2)	0.06099 (17)	0.10584 (6)	0.0476 (5)
N2	0.2955 (2)	0.20995 (16)	0.13575 (5)	0.0402 (4)
N3	0.5465 (3)	0.40018 (18)	0.16171 (7)	0.0531 (5)
O1	0.7299 (3)	0.00518 (18)	0.05473 (6)	0.0730 (6)
O2	0.4270 (3)	−0.35051 (16)	0.19254 (5)	0.0772 (7)
O3	0.2539 (2)	0.18744 (16)	0.21413 (5)	0.0614 (5)
O4	0.1785 (3)	0.37724 (19)	0.22274 (6)	0.0777 (6)
O5	−0.0475 (3)	0.70850 (19)	0.03026 (7)	0.0815 (6)
O6	0.5102 (2)	0.3667 (2)	0.19483 (6)	0.0699 (6)
O7	0.6700 (2)	0.4365 (2)	0.15328 (7)	0.0782 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (12)	0.0404 (11)	0.0429 (11)	−0.0039 (10)	0.0002 (10)	0.0047 (9)
C2	0.0392 (11)	0.0484 (13)	0.0519 (12)	−0.0036 (10)	0.0007 (10)	0.0082 (10)
C3	0.0535 (14)	0.0512 (13)	0.0508 (13)	0.0027 (12)	0.0079 (11)	0.0064 (11)
C4	0.0432 (11)	0.0373 (10)	0.0371 (10)	−0.0031 (9)	−0.0003 (9)	0.0023 (9)
C5	0.0466 (12)	0.0394 (11)	0.0464 (11)	−0.0039 (10)	−0.0068 (10)	0.0027 (9)
C6	0.0509 (13)	0.0396 (11)	0.0452 (12)	−0.0006 (11)	−0.0026 (10)	−0.0048 (10)
C7	0.0449 (11)	0.0428 (11)	0.0377 (10)	0.0001 (11)	−0.0014 (9)	−0.0024 (9)
C8	0.0424 (12)	0.0563 (14)	0.0540 (13)	0.0024 (12)	−0.0023 (11)	0.0022 (11)
C9	0.0394 (12)	0.0631 (15)	0.0419 (11)	−0.0043 (11)	−0.0057 (10)	0.0048 (11)
C10	0.0426 (13)	0.0831 (19)	0.0546 (14)	−0.0019 (14)	−0.0012 (12)	0.0051 (14)
C11	0.0568 (16)	0.091 (2)	0.0629 (16)	−0.0254 (17)	0.0044 (14)	0.0133 (16)
C12	0.074 (2)	0.0660 (18)	0.082 (2)	−0.0271 (18)	0.0046 (17)	0.0048 (16)
C13	0.0657 (18)	0.0564 (15)	0.0716 (17)	−0.0199 (15)	0.0026 (15)	−0.0070 (13)
C14	0.0469 (13)	0.0582 (14)	0.0463 (12)	−0.0132 (12)	−0.0050 (10)	−0.0018 (11)
C15	0.0487 (13)	0.0488 (12)	0.0464 (12)	−0.0099 (11)	0.0007 (11)	−0.0088 (10)
C16	0.0530 (14)	0.0380 (11)	0.0498 (12)	−0.0001 (11)	−0.0011 (11)	−0.0026 (10)
C17	0.0734 (18)	0.0538 (14)	0.0531 (14)	0.0148 (14)	−0.0002 (13)	−0.0067 (12)
C18	0.0713 (18)	0.0537 (15)	0.0723 (17)	0.0186 (14)	−0.0074 (15)	−0.0066 (14)
C19	0.0673 (17)	0.0438 (13)	0.0665 (15)	0.0025 (13)	−0.0126 (14)	0.0081 (12)
C20	0.0722 (17)	0.0584 (15)	0.0488 (13)	0.0083 (15)	−0.0034 (13)	0.0048 (11)
C21	0.0643 (16)	0.0488 (13)	0.0520 (13)	0.0105 (13)	0.0008 (12)	0.0006 (11)
C22	0.0410 (12)	0.0519 (13)	0.0524 (13)	−0.0002 (11)	0.0046 (10)	0.0104 (11)
C23	0.0612 (16)	0.0583 (16)	0.0689 (16)	−0.0106 (14)	−0.0019 (14)	0.0140 (13)
C24	0.093 (2)	0.0612 (18)	0.093 (2)	−0.0071 (18)	0.005 (2)	0.0275 (17)
C25	0.085 (2)	0.089 (2)	0.0730 (19)	0.013 (2)	0.0069 (18)	0.0370 (18)
C26	0.0676 (18)	0.102 (2)	0.0499 (14)	0.0056 (18)	−0.0012 (13)	0.0150 (16)
C27	0.0539 (15)	0.0645 (15)	0.0506 (13)	−0.0039 (13)	0.0025 (12)	0.0048 (12)
C28	0.0497 (13)	0.0423 (12)	0.0493 (12)	−0.0023 (11)	0.0018 (11)	0.0062 (10)
C29	0.0641 (16)	0.0421 (12)	0.0584 (14)	0.0028 (12)	0.0105 (13)	0.0037 (11)
C30	0.0681 (17)	0.0518 (14)	0.0537 (14)	−0.0077 (14)	0.0097 (13)	0.0072 (11)
C31	0.0806 (19)	0.0440 (13)	0.0504 (13)	−0.0154 (14)	−0.0013 (14)	0.0043 (11)
C32	0.110 (3)	0.0406 (13)	0.0590 (15)	−0.0050 (16)	0.0063 (17)	−0.0015 (12)
C33	0.085 (2)	0.0484 (14)	0.0507 (13)	−0.0015 (14)	0.0103 (14)	0.0000 (11)
C34	0.168 (4)	0.074 (2)	0.0659 (19)	−0.049 (3)	0.029 (2)	0.0030 (17)
C35	0.0561 (14)	0.0558 (14)	0.0406 (11)	−0.0051 (13)	0.0009 (11)	−0.0045 (11)
C36A	0.185 (11)	0.086 (5)	0.027 (3)	−0.057 (6)	−0.007 (5)	0.006 (3)
C36B	0.052 (6)	0.17 (2)	0.066 (9)	0.037 (11)	−0.012 (5)	0.039 (9)
C37A	0.100 (6)	0.179 (13)	0.062 (4)	−0.039 (7)	0.002 (4)	0.032 (6)
C37B	0.26 (3)	0.073 (9)	0.056 (6)	0.017 (12)	0.060 (12)	0.022 (6)
C38	0.108 (3)	0.091 (2)	0.082 (2)	0.013 (2)	−0.021 (2)	0.0345 (18)
N1	0.0521 (11)	0.0395 (10)	0.0512 (10)	0.0007 (9)	0.0073 (9)	0.0045 (8)
N2	0.0409 (10)	0.0394 (9)	0.0404 (9)	−0.0045 (8)	0.0009 (8)	−0.0033 (8)
N3	0.0540 (13)	0.0427 (10)	0.0625 (13)	−0.0060 (10)	−0.0127 (11)	−0.0022 (10)
O1	0.0886 (15)	0.0584 (11)	0.0719 (12)	0.0103 (11)	0.0320 (12)	0.0013 (10)
O2	0.1283 (19)	0.0457 (10)	0.0576 (10)	−0.0274 (12)	0.0074 (12)	0.0055 (8)
O3	0.0868 (13)	0.0590 (10)	0.0386 (8)	−0.0079 (10)	−0.0050 (9)	0.0070 (8)
O4	0.1063 (18)	0.0765 (13)	0.0502 (10)	0.0096 (13)	0.0095 (11)	−0.0168 (10)
O5	0.0965 (16)	0.0656 (12)	0.0824 (14)	0.0216 (13)	−0.0214 (13)	0.0100 (11)
O6	0.0764 (13)	0.0744 (13)	0.0590 (11)	−0.0144 (11)	−0.0207 (10)	0.0107 (10)
O7	0.0528 (12)	0.0899 (15)	0.0921 (14)	−0.0189 (12)	−0.0117 (11)	−0.0037 (12)

C1—N1	1.482 (3)	C22—C23	1.377 (4)
C1—C4	1.517 (3)	C22—C27	1.380 (4)
C1—C2	1.577 (3)	C23—C24	1.386 (4)
C1—H1	0.9800	C23—H23	0.9300
C2—C22	1.504 (3)	C24—C25	1.369 (5)
C2—C3	1.524 (4)	C24—H24	0.9300
C2—H2	0.9800	C25—C26	1.362 (5)
C3—O1	1.197 (3)	C25—H25	0.9300
C3—N1	1.378 (3)	C26—C27	1.384 (4)
C4—N2	1.464 (3)	C26—H26	0.9300
C4—C5	1.542 (3)	C27—H27	0.9300
C4—H4	0.9800	C28—C29	1.376 (4)
C5—N3	1.511 (3)	C28—C33	1.395 (3)
C5—C6	1.524 (3)	C28—N1	1.406 (3)
C5—H5	0.9800	C29—C30	1.384 (3)
C6—C16	1.514 (3)	C29—H29	0.9300
C6—C7	1.561 (3)	C30—C31	1.366 (4)
C6—H6	0.9800	C30—H30	0.9300
C7—N2	1.474 (3)	C31—O2	1.369 (3)
C7—C35	1.538 (3)	C31—C32	1.388 (4)
C7—C8	1.545 (3)	C32—C33	1.367 (4)
C8—C9	1.496 (4)	C32—H32	0.9300
C8—H8A	0.9700	C33—H33	0.9300
C8—H8B	0.9700	C34—O2	1.424 (4)
C9—C10	1.385 (4)	C34—H34A	0.9600
C9—C14	1.388 (4)	C34—H34B	0.9600
C10—C11	1.377 (4)	C34—H34C	0.9600
C10—H10	0.9300	C35—O4	1.198 (3)
C11—C12	1.370 (5)	C35—O3	1.322 (3)
C11—H11	0.9300	C36A—C37A	1.240 (17)
C12—C13	1.380 (4)	C36A—O3	1.448 (8)
C12—H12	0.9300	C36A—H36A	0.9700
C13—C14	1.380 (4)	C36A—H36B	0.9700
C13—H13	0.9300	C36B—O3	1.49 (2)
C14—C15	1.497 (3)	C36B—C37B	1.60 (3)
C15—N2	1.474 (3)	C36B—H36C	0.9700
C15—H15A	0.9700	C36B—H36D	0.9700
C15—H15B	0.9700	C37A—H37A	0.9600
C16—C21	1.384 (3)	C37A—H37B	0.9600
C16—C17	1.390 (3)	C37A—H37C	0.9600
C17—C18	1.366 (4)	C37B—H37D	0.9600
C17—H17	0.9300	C37B—H37E	0.9600
C18—C19	1.387 (4)	C37B—H37F	0.9600
C18—H18	0.9300	C38—O5	1.408 (4)
C19—C20	1.368 (4)	C38—H38A	0.9600
C19—O5	1.379 (3)	C38—H38B	0.9600
C20—C21	1.385 (4)	C38—H38C	0.9600
C20—H20	0.9300	N3—O6	1.211 (3)
C21—H21	0.9300	N3—O7	1.217 (3)
N1—C1—C4	117.82 (19)	C23—C22—C2	119.9 (2)
N1—C1—C2	87.16 (17)	C27—C22—C2	121.4 (2)
C4—C1—C2	115.87 (17)	C22—C23—C24	120.1 (3)
N1—C1—H1	111.3	C22—C23—H23	120.0
C4—C1—H1	111.3	C24—C23—H23	120.0
C2—C1—H1	111.3	C25—C24—C23	120.8 (3)
C22—C2—C3	118.6 (2)	C25—C24—H24	119.6
C22—C2—C1	119.5 (2)	C23—C24—H24	119.6
C3—C2—C1	85.25 (17)	C26—C25—C24	119.3 (3)
C22—C2—H2	110.4	C26—C25—H25	120.4
C3—C2—H2	110.4	C24—C25—H25	120.4
C1—C2—H2	110.4	C25—C26—C27	120.4 (3)
O1—C3—N1	131.5 (2)	C25—C26—H26	119.8
O1—C3—C2	135.4 (2)	C27—C26—H26	119.8
N1—C3—C2	93.13 (19)	C22—C27—C26	120.7 (3)
N2—C4—C1	114.74 (16)	C22—C27—H27	119.7
N2—C4—C5	105.44 (17)	C26—C27—H27	119.7
C1—C4—C5	113.11 (18)	C29—C28—C33	119.2 (2)
N2—C4—H4	107.7	C29—C28—N1	121.0 (2)
C1—C4—H4	107.7	C33—C28—N1	119.8 (2)
C5—C4—H4	107.7	C28—C29—C30	120.7 (2)
N3—C5—C6	111.29 (19)	C28—C29—H29	119.6
N3—C5—C4	109.85 (18)	C30—C29—H29	119.6
C6—C5—C4	105.74 (18)	C31—C30—C29	120.1 (2)
N3—C5—H5	110.0	C31—C30—H30	120.0
C6—C5—H5	110.0	C29—C30—H30	120.0
C4—C5—H5	110.0	C30—C31—O2	125.0 (2)
C16—C6—C5	112.48 (19)	C30—C31—C32	119.4 (2)
C16—C6—C7	115.8 (2)	O2—C31—C32	115.6 (2)
C5—C6—C7	103.80 (18)	C33—C32—C31	121.1 (3)
C16—C6—H6	108.1	C33—C32—H32	119.5
C5—C6—H6	108.1	C31—C32—H32	119.5
C7—C6—H6	108.1	C32—C33—C28	119.5 (2)
N2—C7—C35	111.71 (19)	C32—C33—H33	120.2
N2—C7—C8	111.33 (19)	C28—C33—H33	120.2
C35—C7—C8	103.68 (19)	O2—C34—H34A	109.5
N2—C7—C6	106.29 (17)	O2—C34—H34B	109.5
C35—C7—C6	109.46 (19)	H34A—C34—H34B	109.5
C8—C7—C6	114.5 (2)	O2—C34—H34C	109.5
C9—C8—C7	109.2 (2)	H34A—C34—H34C	109.5
C9—C8—H8A	109.8	H34B—C34—H34C	109.5
C7—C8—H8A	109.8	O4—C35—O3	124.4 (2)
C9—C8—H8B	109.8	O4—C35—C7	121.9 (2)
C7—C8—H8B	109.8	O3—C35—C7	113.5 (2)
H8A—C8—H8B	108.3	C37A—C36A—O3	122.8 (11)
C10—C9—C14	119.5 (3)	C37A—C36A—H36A	106.6
C10—C9—C8	125.2 (3)	O3—C36A—H36A	106.6
C14—C9—C8	115.2 (2)	C37A—C36A—H36B	106.6
C11—C10—C9	119.8 (3)	O3—C36A—H36B	106.6
C11—C10—H10	120.1	H36A—C36A—H36B	106.6
C9—C10—H10	120.1	O3—C36B—C37B	100.1 (15)
C12—C11—C10	120.6 (3)	O3—C36B—H36C	111.7
C12—C11—H11	119.7	C37B—C36B—H36C	111.7
C10—C11—H11	119.7	O3—C36B—H36D	111.7
C11—C12—C13	120.2 (3)	C37B—C36B—H36D	111.7
C11—C12—H12	119.9	H36C—C36B—H36D	109.5
C13—C12—H12	119.9	C36A—C37A—H37A	109.5
C14—C13—C12	119.7 (3)	C36A—C37A—H37B	109.5
C14—C13—H13	120.2	H37A—C37A—H37B	109.5
C12—C13—H13	120.2	C36A—C37A—H37C	109.5
C13—C14—C9	120.2 (3)	H37A—C37A—H37C	109.5
C13—C14—C15	123.9 (3)	H37B—C37A—H37C	109.5
C9—C14—C15	115.8 (2)	C36B—C37B—H37D	109.5
N2—C15—C14	109.52 (18)	C36B—C37B—H37E	109.5
N2—C15—H15A	109.8	H37D—C37B—H37E	109.5
C14—C15—H15A	109.8	C36B—C37B—H37F	109.5
N2—C15—H15B	109.8	H37D—C37B—H37F	109.5
C14—C15—H15B	109.8	H37E—C37B—H37F	109.5
H15A—C15—H15B	108.2	O5—C38—H38A	109.5
C21—C16—C17	116.7 (2)	O5—C38—H38B	109.5
C21—C16—C6	124.1 (2)	H38A—C38—H38B	109.5
C17—C16—C6	119.2 (2)	O5—C38—H38C	109.5
C18—C17—C16	122.1 (2)	H38A—C38—H38C	109.5
C18—C17—H17	118.9	H38B—C38—H38C	109.5
C16—C17—H17	118.9	C3—N1—C28	130.0 (2)
C17—C18—C19	120.0 (3)	C3—N1—C1	94.42 (18)
C17—C18—H18	120.0	C28—N1—C1	129.14 (19)
C19—C18—H18	120.0	C4—N2—C7	111.06 (17)
C20—C19—O5	124.8 (3)	C4—N2—C15	111.80 (16)
C20—C19—C18	119.3 (2)	C7—N2—C15	115.71 (18)
O5—C19—C18	115.9 (3)	O6—N3—O7	124.1 (2)
C19—C20—C21	120.0 (2)	O6—N3—C5	118.8 (2)
C19—C20—H20	120.0	O7—N3—C5	117.1 (2)
C21—C20—H20	120.0	C31—O2—C34	116.7 (2)
C16—C21—C20	121.9 (3)	C35—O3—C36A	113.4 (5)
C16—C21—H21	119.1	C35—O3—C36B	119.7 (10)
C20—C21—H21	119.1	C36A—O3—C36B	17.5 (10)
C23—C22—C27	118.6 (2)	C19—O5—C38	117.4 (3)
N1—C1—C2—C22	119.1 (2)	C2—C22—C23—C24	−175.0 (3)
C4—C1—C2—C22	−0.6 (3)	C22—C23—C24—C25	−0.3 (5)
N1—C1—C2—C3	−1.17 (17)	C23—C24—C25—C26	−1.6 (5)
C4—C1—C2—C3	−120.9 (2)	C24—C25—C26—C27	1.6 (5)
C22—C2—C3—O1	61.1 (4)	C23—C22—C27—C26	−2.3 (4)
C1—C2—C3—O1	−177.8 (3)	C2—C22—C27—C26	174.9 (3)
C22—C2—C3—N1	−119.9 (2)	C25—C26—C27—C22	0.4 (5)
C1—C2—C3—N1	1.26 (18)	C33—C28—C29—C30	−0.6 (4)
N1—C1—C4—N2	58.1 (3)	N1—C28—C29—C30	−178.7 (3)
C2—C1—C4—N2	159.31 (18)	C28—C29—C30—C31	−0.9 (5)
N1—C1—C4—C5	179.16 (17)	C29—C30—C31—O2	−179.4 (3)
C2—C1—C4—C5	−79.7 (2)	C29—C30—C31—C32	2.2 (5)
N2—C4—C5—N3	94.8 (2)	C30—C31—C32—C33	−1.9 (5)
C1—C4—C5—N3	−31.3 (3)	O2—C31—C32—C33	179.5 (3)
N2—C4—C5—C6	−25.4 (2)	C31—C32—C33—C28	0.4 (5)
C1—C4—C5—C6	−151.54 (18)	C29—C28—C33—C32	0.9 (5)
N3—C5—C6—C16	142.32 (19)	N1—C28—C33—C32	179.0 (3)
C4—C5—C6—C16	−98.4 (2)	N2—C7—C35—O4	164.9 (2)
N3—C5—C6—C7	−91.7 (2)	C8—C7—C35—O4	−75.2 (3)
C4—C5—C6—C7	27.5 (2)	C6—C7—C35—O4	47.4 (3)
C16—C6—C7—N2	103.9 (2)	N2—C7—C35—O3	−20.1 (3)
C5—C6—C7—N2	−19.9 (2)	C8—C7—C35—O3	99.9 (3)
C16—C6—C7—C35	−135.3 (2)	C6—C7—C35—O3	−137.6 (2)
C5—C6—C7—C35	100.9 (2)	O1—C3—N1—C28	24.7 (5)
C16—C6—C7—C8	−19.4 (3)	C2—C3—N1—C28	−154.4 (2)
C5—C6—C7—C8	−143.24 (19)	O1—C3—N1—C1	177.8 (3)
N2—C7—C8—C9	49.1 (2)	C2—C3—N1—C1	−1.34 (19)
C35—C7—C8—C9	−71.1 (2)	C29—C28—N1—C3	159.1 (3)
C6—C7—C8—C9	169.71 (18)	C33—C28—N1—C3	−19.0 (4)
C7—C8—C9—C10	125.3 (2)	C29—C28—N1—C1	14.7 (4)
C7—C8—C9—C14	−51.4 (3)	C33—C28—N1—C1	−163.4 (3)
C14—C9—C10—C11	−1.5 (4)	C4—C1—N1—C3	119.2 (2)
C8—C9—C10—C11	−178.1 (3)	C2—C1—N1—C3	1.30 (19)
C9—C10—C11—C12	0.6 (4)	C4—C1—N1—C28	−87.3 (3)
C10—C11—C12—C13	0.3 (5)	C2—C1—N1—C28	154.8 (2)
C11—C12—C13—C14	−0.3 (5)	C1—C4—N2—C7	138.00 (18)
C12—C13—C14—C9	−0.5 (4)	C5—C4—N2—C7	12.9 (2)
C12—C13—C14—C15	175.9 (2)	C1—C4—N2—C15	−91.1 (2)
C10—C9—C14—C13	1.4 (4)	C5—C4—N2—C15	143.76 (19)
C8—C9—C14—C13	178.3 (2)	C35—C7—N2—C4	−114.9 (2)
C10—C9—C14—C15	−175.3 (2)	C8—C7—N2—C4	129.7 (2)
C8—C9—C14—C15	1.7 (3)	C6—C7—N2—C4	4.4 (2)
C13—C14—C15—N2	−127.0 (3)	C35—C7—N2—C15	116.2 (2)
C9—C14—C15—N2	49.5 (3)	C8—C7—N2—C15	0.8 (3)
C5—C6—C16—C21	29.0 (3)	C6—C7—N2—C15	−124.4 (2)
C7—C6—C16—C21	−90.2 (3)	C14—C15—N2—C4	−178.13 (19)
C5—C6—C16—C17	−150.5 (2)	C14—C15—N2—C7	−49.7 (3)
C7—C6—C16—C17	90.3 (3)	C6—C5—N3—O6	40.4 (3)
C21—C16—C17—C18	0.3 (4)	C4—C5—N3—O6	−76.4 (3)
C6—C16—C17—C18	179.9 (3)	C6—C5—N3—O7	−142.3 (2)
C16—C17—C18—C19	−1.4 (5)	C4—C5—N3—O7	101.0 (2)
C17—C18—C19—C20	1.2 (5)	C30—C31—O2—C34	2.4 (5)
C17—C18—C19—O5	−178.5 (3)	C32—C31—O2—C34	−179.1 (3)
O5—C19—C20—C21	179.7 (3)	O4—C35—O3—C36A	8.5 (8)
C18—C19—C20—C21	0.0 (4)	C7—C35—O3—C36A	−166.4 (7)
C17—C16—C21—C20	1.0 (4)	O4—C35—O3—C36B	−9.9 (10)
C6—C16—C21—C20	−178.6 (3)	C7—C35—O3—C36B	175.3 (9)
C19—C20—C21—C16	−1.1 (5)	C37A—C36A—O3—C35	106.6 (10)
C3—C2—C22—C23	−156.6 (3)	C37A—C36A—O3—C36B	−139 (5)
C1—C2—C22—C23	101.9 (3)	C37B—C36B—O3—C35	132.2 (15)
C3—C2—C22—C27	26.2 (3)	C37B—C36B—O3—C36A	59 (4)
C1—C2—C22—C27	−75.3 (3)	C20—C19—O5—C38	−1.1 (5)
C27—C22—C23—C24	2.3 (4)	C18—C19—O5—C38	178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.98	2.42	3.260 (3)	143
C20—H20···O1ii	0.93	2.47	3.397 (3)	172
C29—H29···O3	0.93	2.59	3.442 (3)	152
C29—H29···N2	0.93	2.50	3.168 (3)	128
C33—H33···O1	0.93	2.44	3.054 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.98	2.42	3.260 (3)	143
C20—H20⋯O1ii	0.93	2.47	3.397 (3)	172
C29—H29⋯O3	0.93	2.59	3.442 (3)	152
C29—H29⋯N2	0.93	2.50	3.168 (3)	128
C33—H33⋯O1	0.93	2.44	3.054 (4)	123

Symmetry codes: (i) ; (ii) .