(S)-Methyl 2-[(3R,4R)-2-benzyl-3-(2-fur-yl)-1-oxo-1,2,3,4-tetra-hydro-isoquinoline-4-carboxamido]-3-(1H-indol-3-yl)propanoate.

The title compound, C(33)H(29)N(3)O(5), was synthesized by the reaction of racemic trans-2-benzyl-3-(2-fur-yl)-1-oxo-1,2,3,4-tetra-hydro-isoquinoline-4-carboxylic acid, l-tryptophan methyl ester and diisopropylcarbodiimide in dry dichloro-methane. The furan ring is disordered over two positions in a 0.859 (14):0.141 (14) ratio. In the 1,2,3,4-tetra-hydro-iso-quin-oline ring system, the heterocyclic ring is not planar, with puckering parameters Q(T) = 0.448 (2) Å, θ = 64.9 (3) and ϕ = 268.3 (3)°. The crystal is extended into a three-dimensional supra-molecular architecture through inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions. The absolute structure was assigned by reference to the chiral starting material.

Related literature

For the synthesis of new heterocyclic compounds with pharmacological activities, see: Bogdanov et al. (2007 ▶); Burdzhiev & Stanoeva (2006 ▶); Kandinska et al. (2006 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C33H29N3O5

M = 547.59

Monoclinic,

a = 8.6866 (5) Å

b = 15.8630 (7) Å

c = 10.5480 (6) Å

β = 104.543 (5)°

V = 1406.90 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.60 × 0.54 × 0.36 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.949, T max = 0.969

8814 measured reflections

3010 independent reflections

2613 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.082

S = 1.02

3010 reflections

409 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.10 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902025X/hb2987sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902025X/hb2987Isup2.hkl

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

C33H29N3O5	F(000) = 576
Mr = 547.59	Dx = 1.293 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 15289 reflections
a = 8.6866 (5) Å	θ = 2.0–28.1°
b = 15.8630 (7) Å	µ = 0.09 mm−1
c = 10.5480 (6) Å	T = 296 K
β = 104.543 (5)°	Prism, colourless
V = 1406.90 (13) Å3	0.60 × 0.54 × 0.36 mm
Z = 2

Stoe IPDS-2 diffractometer	3010 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2613 reflections with I > 2σ(I)
plane graphite	Rint = 0.034
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
Tmin = 0.949, Tmax = 0.969	l = −13→13
8814 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.0571P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3010 reflections	Δρmax = 0.11 e Å−3
409 parameters	Δρmin = −0.10 e Å−3
16 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001Fc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
O1	0.7796 (3)	0.13450 (15)	0.8595 (2)	0.0877 (8)
O2	0.8751 (3)	0.20882 (15)	1.04255 (18)	0.0900 (8)
O3	0.5503 (2)	0.39216 (9)	0.73029 (15)	0.0623 (5)
O4	0.7409 (2)	0.14390 (12)	0.4350 (2)	0.0714 (7)
O5	0.3408 (6)	0.3203 (3)	0.2533 (3)	0.0832 (15)	0.859 (14)
N1	0.4577 (3)	0.03542 (17)	1.0943 (2)	0.0817 (10)
N2	0.5562 (3)	0.25261 (12)	0.76349 (16)	0.0559 (6)
N3	0.6645 (2)	0.27926 (11)	0.45137 (17)	0.0475 (5)
C1	0.3339 (4)	0.04232 (19)	0.9851 (3)	0.0717 (10)
C2	0.2120 (5)	−0.0141 (2)	0.9326 (3)	0.0926 (14)
C3	0.0984 (5)	0.0105 (3)	0.8234 (3)	0.0994 (14)
C4	0.1055 (5)	0.0888 (3)	0.7664 (3)	0.1012 (13)
C5	0.2279 (4)	0.1442 (2)	0.8179 (3)	0.0822 (11)
C6	0.3448 (3)	0.12196 (17)	0.9300 (2)	0.0655 (9)
C7	0.4798 (3)	0.16422 (17)	1.0120 (2)	0.0654 (9)
C8	0.5422 (4)	0.1086 (2)	1.1101 (2)	0.0751 (10)
C9	0.5382 (4)	0.25128 (18)	0.9959 (2)	0.0731 (9)
C10	0.6440 (3)	0.25915 (15)	0.8994 (2)	0.0631 (8)
C11	0.7722 (3)	0.19342 (17)	0.9276 (2)	0.0638 (8)
C12	0.9983 (5)	0.1470 (3)	1.0888 (4)	0.1111 (14)
C13	0.5186 (2)	0.32068 (13)	0.68794 (18)	0.0442 (6)
C14	0.4349 (2)	0.30917 (13)	0.54335 (18)	0.0424 (6)
C15	0.3774 (2)	0.22153 (12)	0.50037 (18)	0.0422 (6)
C16	0.2255 (3)	0.19519 (15)	0.4982 (2)	0.0525 (7)
C17	0.1728 (3)	0.11632 (16)	0.4523 (2)	0.0596 (8)
C18	0.2738 (3)	0.06173 (15)	0.4106 (2)	0.0598 (8)
C19	0.4266 (3)	0.08634 (14)	0.4148 (2)	0.0541 (7)
C20	0.4788 (2)	0.16665 (13)	0.45772 (18)	0.0449 (6)
C21	0.6383 (2)	0.19472 (14)	0.44794 (19)	0.0490 (7)
C22	0.5424 (2)	0.34225 (13)	0.45839 (18)	0.0457 (6)
C23	0.4504 (3)	0.37158 (14)	0.3274 (2)	0.0552 (7)
C24	0.4590 (11)	0.4436 (3)	0.2647 (4)	0.0905 (19)	0.859 (14)
C25	0.3411 (11)	0.4410 (4)	0.1445 (5)	0.101 (2)	0.859 (14)
C26	0.2724 (10)	0.3674 (7)	0.1422 (7)	0.106 (3)	0.859 (14)
C27	0.8112 (3)	0.31240 (18)	0.4263 (2)	0.0591 (8)
C28	0.9227 (2)	0.34976 (14)	0.5463 (2)	0.0502 (7)
C29	0.9300 (3)	0.3188 (2)	0.6691 (2)	0.0682 (8)
C30	1.0360 (4)	0.3530 (3)	0.7775 (3)	0.0895 (13)
C31	1.1350 (4)	0.4169 (2)	0.7639 (3)	0.0872 (11)
C32	1.1294 (3)	0.44850 (17)	0.6434 (3)	0.0751 (9)
C33	1.0234 (3)	0.41541 (15)	0.5341 (3)	0.0615 (8)
C25'	0.273 (4)	0.346 (2)	0.134 (3)	0.069 (10)	0.141 (14)
C26'	0.280 (3)	0.4291 (17)	0.162 (3)	0.088 (13)	0.141 (14)
C24'	0.385 (3)	0.3089 (12)	0.246 (2)	0.043 (6)	0.141 (14)
O5'	0.390 (3)	0.4486 (14)	0.281 (3)	0.127 (13)	0.141 (14)
H3	0.01520	−0.02590	0.78690	0.1190*
H2A	0.52760	0.20370	0.73080	0.0670*
H8	0.63080	0.11920	1.17880	0.0900*
H4	0.02690	0.10420	0.69260	0.1210*
H5	0.23240	0.19610	0.77810	0.0990*
H10	0.69520	0.31460	0.91210	0.0760*
H12A	1.05840	0.13960	1.02470	0.1340*
H12B	0.95090	0.09430	1.10290	0.1340*
H12C	1.06760	0.16600	1.16960	0.1340*
H14	0.34070	0.34550	0.52550	0.0510*
H9A	0.59770	0.27150	1.08090	0.0880*
H9B	0.44690	0.28800	0.96650	0.0880*
H18	0.23840	0.00840	0.37970	0.0720*
H19	0.49550	0.04910	0.38890	0.0650*
H22	0.59860	0.39150	0.50370	0.0550*
H24	0.52950	0.48760	0.29450	0.1090*	0.859 (14)
H25	0.31740	0.48270	0.08070	0.1220*	0.859 (14)
H26	0.18840	0.34880	0.07470	0.1270*	0.859 (14)
H27A	0.78420	0.35540	0.35890	0.0710*
H27B	0.86550	0.26720	0.39320	0.0710*
H29	0.86360	0.27480	0.67960	0.0820*
H30	1.03940	0.33200	0.86040	0.1070*
H31	1.20660	0.43880	0.83730	0.1050*
H32	1.19670	0.49240	0.63410	0.0900*
H33	1.01980	0.43740	0.45170	0.0740*
H16	0.15770	0.23110	0.52810	0.0630*
H17	0.06920	0.09980	0.44940	0.0720*
H1	0.47870	−0.00800	1.14460	0.0980*
H2	0.20770	−0.06670	0.97030	0.1110*
H24'	0.40720	0.25180	0.25950	0.0520*	0.141 (14)
H25'	0.21150	0.31920	0.06070	0.0840*	0.141 (14)
H26'	0.21840	0.46940	0.10880	0.1060*	0.141 (14)

	U11	U22	U33	U12	U13	U23
O1	0.0850 (14)	0.0796 (14)	0.0907 (14)	0.0121 (11)	0.0078 (11)	−0.0070 (11)
O2	0.0954 (15)	0.0963 (16)	0.0643 (11)	−0.0005 (12)	−0.0062 (10)	0.0093 (10)
O3	0.0906 (12)	0.0369 (8)	0.0542 (8)	−0.0009 (8)	0.0084 (8)	−0.0075 (7)
O4	0.0567 (10)	0.0609 (11)	0.0991 (13)	0.0151 (9)	0.0240 (9)	−0.0105 (9)
O5	0.086 (3)	0.092 (3)	0.0578 (17)	−0.009 (2)	−0.0076 (14)	0.0135 (15)
N1	0.0965 (18)	0.0772 (17)	0.0752 (15)	0.0155 (15)	0.0288 (13)	0.0313 (12)
N2	0.0781 (13)	0.0367 (9)	0.0477 (9)	−0.0064 (9)	0.0062 (8)	−0.0007 (7)
N3	0.0401 (8)	0.0474 (10)	0.0548 (9)	−0.0010 (8)	0.0116 (7)	−0.0024 (7)
C1	0.0840 (19)	0.0725 (17)	0.0662 (14)	0.0151 (15)	0.0333 (14)	0.0193 (13)
C2	0.111 (3)	0.083 (2)	0.095 (2)	−0.003 (2)	0.047 (2)	0.0175 (18)
C3	0.099 (2)	0.119 (3)	0.086 (2)	−0.023 (2)	0.0338 (19)	0.013 (2)
C4	0.091 (2)	0.140 (3)	0.0739 (18)	−0.010 (2)	0.0232 (16)	0.027 (2)
C5	0.088 (2)	0.094 (2)	0.0674 (16)	0.0045 (18)	0.0250 (15)	0.0286 (15)
C6	0.0792 (16)	0.0700 (16)	0.0543 (12)	0.0158 (14)	0.0301 (12)	0.0154 (11)
C7	0.0897 (18)	0.0642 (15)	0.0479 (12)	0.0188 (14)	0.0277 (12)	0.0099 (11)
C8	0.0902 (18)	0.084 (2)	0.0525 (13)	0.0158 (17)	0.0207 (12)	0.0141 (13)
C9	0.110 (2)	0.0568 (14)	0.0521 (12)	0.0172 (15)	0.0195 (13)	−0.0027 (11)
C10	0.0926 (18)	0.0425 (11)	0.0479 (11)	−0.0084 (12)	0.0058 (11)	0.0001 (9)
C11	0.0714 (15)	0.0610 (15)	0.0554 (12)	−0.0085 (13)	0.0095 (11)	0.0075 (11)
C12	0.092 (2)	0.141 (3)	0.086 (2)	0.018 (2)	−0.0044 (18)	0.030 (2)
C13	0.0492 (10)	0.0376 (10)	0.0473 (10)	0.0005 (9)	0.0149 (8)	−0.0032 (8)
C14	0.0434 (9)	0.0355 (10)	0.0479 (10)	0.0042 (8)	0.0105 (8)	−0.0021 (8)
C15	0.0445 (10)	0.0378 (10)	0.0423 (9)	−0.0006 (8)	0.0074 (8)	0.0002 (7)
C16	0.0470 (11)	0.0539 (13)	0.0571 (12)	−0.0009 (11)	0.0138 (9)	−0.0017 (10)
C17	0.0518 (12)	0.0590 (14)	0.0651 (13)	−0.0142 (11)	0.0092 (10)	0.0024 (11)
C18	0.0699 (15)	0.0418 (12)	0.0622 (13)	−0.0121 (11)	0.0064 (11)	−0.0043 (10)
C19	0.0627 (13)	0.0405 (12)	0.0578 (12)	0.0037 (10)	0.0128 (10)	−0.0044 (9)
C20	0.0475 (11)	0.0379 (10)	0.0474 (10)	0.0021 (9)	0.0083 (8)	−0.0024 (8)
C21	0.0451 (11)	0.0486 (12)	0.0515 (11)	0.0078 (10)	0.0088 (9)	−0.0064 (9)
C22	0.0515 (11)	0.0375 (10)	0.0464 (10)	−0.0007 (9)	0.0094 (8)	−0.0005 (8)
C23	0.0657 (14)	0.0493 (13)	0.0505 (11)	0.0076 (11)	0.0144 (10)	0.0010 (9)
C24	0.140 (5)	0.058 (2)	0.067 (2)	0.001 (3)	0.014 (3)	0.0133 (17)
C25	0.156 (6)	0.089 (3)	0.059 (2)	0.053 (4)	0.027 (3)	0.025 (2)
C26	0.105 (6)	0.142 (7)	0.054 (3)	0.011 (5)	−0.014 (3)	0.009 (4)
C27	0.0488 (11)	0.0696 (15)	0.0609 (13)	−0.0075 (12)	0.0175 (10)	0.0001 (11)
C28	0.0380 (10)	0.0452 (11)	0.0675 (13)	0.0024 (9)	0.0133 (9)	0.0017 (9)
C29	0.0559 (13)	0.0757 (16)	0.0675 (14)	−0.0098 (13)	0.0052 (11)	0.0103 (13)
C30	0.0757 (17)	0.113 (3)	0.0682 (16)	−0.0181 (18)	−0.0037 (13)	0.0065 (16)
C31	0.0659 (17)	0.093 (2)	0.090 (2)	−0.0139 (17)	−0.0041 (14)	−0.0100 (17)
C32	0.0493 (13)	0.0509 (14)	0.121 (2)	−0.0071 (12)	0.0136 (14)	−0.0062 (15)
C33	0.0497 (12)	0.0516 (13)	0.0825 (16)	0.0002 (11)	0.0152 (11)	0.0099 (11)
C25'	0.09 (2)	0.077 (17)	0.052 (16)	0.047 (16)	0.039 (16)	0.031 (12)
C26'	0.037 (11)	0.15 (3)	0.08 (2)	0.004 (15)	0.019 (11)	0.08 (2)
C24'	0.045 (11)	0.032 (9)	0.051 (10)	0.007 (8)	0.010 (8)	−0.010 (7)
O5'	0.12 (2)	0.088 (15)	0.18 (3)	0.059 (14)	0.049 (17)	0.023 (14)

O1—C11	1.190 (3)	C24—C25	1.416 (9)
O2—C11	1.336 (3)	C24'—C25'	1.45 (4)
O2—C12	1.443 (5)	C25—C26	1.309 (13)
O3—C13	1.225 (2)	C25'—C26'	1.35 (4)
O4—C21	1.235 (3)	C27—C28	1.509 (3)
O5—C23	1.344 (5)	C28—C33	1.387 (3)
O5—C26	1.391 (9)	C28—C29	1.372 (3)
O5'—C26'	1.41 (4)	C29—C30	1.386 (4)
O5'—C23	1.37 (2)	C30—C31	1.360 (5)
N1—C8	1.361 (4)	C31—C32	1.356 (4)
N1—C1	1.369 (4)	C32—C33	1.385 (4)
N2—C13	1.333 (3)	C2—H2	0.9300
N2—C10	1.449 (3)	C3—H3	0.9300
N3—C22	1.473 (3)	C4—H4	0.9300
N3—C21	1.359 (3)	C5—H5	0.9300
N3—C27	1.463 (3)	C8—H8	0.9300
N1—H1	0.8600	C9—H9A	0.9700
N2—H2A	0.8600	C9—H9B	0.9700
C1—C6	1.404 (4)	C10—H10	0.9800
C1—C2	1.391 (5)	C12—H12A	0.9600
C2—C3	1.372 (5)	C12—H12B	0.9600
C3—C4	1.388 (6)	C12—H12C	0.9600
C4—C5	1.381 (6)	C14—H14	0.9800
C5—C6	1.397 (4)	C16—H16	0.9300
C6—C7	1.436 (4)	C17—H17	0.9300
C7—C8	1.364 (4)	C18—H18	0.9300
C7—C9	1.496 (4)	C19—H19	0.9300
C9—C10	1.538 (4)	C22—H22	0.9800
C10—C11	1.500 (4)	C24—H24	0.9300
C13—C14	1.527 (3)	C24'—H24'	0.9300
C14—C22	1.540 (3)	C25—H25	0.9300
C14—C15	1.508 (3)	C25'—H25'	0.9300
C15—C16	1.379 (3)	C26—H26	0.9300
C15—C20	1.391 (3)	C26'—H26'	0.9300
C16—C17	1.378 (3)	C27—H27A	0.9700
C17—C18	1.381 (4)	C27—H27B	0.9700
C18—C19	1.374 (4)	C29—H29	0.9300
C19—C20	1.389 (3)	C30—H30	0.9300
C20—C21	1.483 (3)	C31—H31	0.9300
C22—C23	1.487 (3)	C32—H32	0.9300
C23—C24'	1.34 (2)	C33—H33	0.9300
C23—C24	1.332 (5)
C11—O2—C12	116.9 (3)	C28—C29—C30	120.2 (3)
C23—O5—C26	104.8 (5)	C29—C30—C31	120.8 (3)
C23—O5'—C26'	103.6 (19)	C30—C31—C32	120.0 (3)
C1—N1—C8	108.7 (2)	C31—C32—C33	120.0 (3)
C10—N2—C13	121.51 (19)	C28—C33—C32	120.7 (3)
C21—N3—C22	123.57 (17)	C1—C2—H2	121.00
C22—N3—C27	115.88 (18)	C3—C2—H2	121.00
C21—N3—C27	119.83 (18)	C2—C3—H3	119.00
C1—N1—H1	126.00	C4—C3—H3	119.00
C8—N1—H1	126.00	C3—C4—H4	120.00
C10—N2—H2A	119.00	C5—C4—H4	120.00
C13—N2—H2A	119.00	C4—C5—H5	120.00
N1—C1—C6	107.5 (3)	C6—C5—H5	120.00
C2—C1—C6	122.6 (3)	N1—C8—H8	124.00
N1—C1—C2	130.0 (3)	C7—C8—H8	125.00
C1—C2—C3	117.8 (3)	C7—C9—H9A	109.00
C2—C3—C4	121.2 (4)	C7—C9—H9B	109.00
C3—C4—C5	120.8 (3)	C10—C9—H9A	108.00
C4—C5—C6	119.8 (3)	C10—C9—H9B	108.00
C5—C6—C7	134.6 (3)	H9A—C9—H9B	107.00
C1—C6—C5	117.9 (3)	N2—C10—H10	108.00
C1—C6—C7	107.5 (2)	C9—C10—H10	108.00
C6—C7—C9	127.7 (2)	C11—C10—H10	108.00
C6—C7—C8	105.3 (2)	O2—C12—H12A	109.00
C8—C7—C9	127.0 (2)	O2—C12—H12B	109.00
N1—C8—C7	111.1 (2)	O2—C12—H12C	109.00
C7—C9—C10	115.2 (2)	H12A—C12—H12B	109.00
C9—C10—C11	110.5 (2)	H12A—C12—H12C	109.00
N2—C10—C11	109.07 (19)	H12B—C12—H12C	109.00
N2—C10—C9	113.3 (2)	C13—C14—H14	107.00
O1—C11—O2	124.5 (3)	C15—C14—H14	107.00
O1—C11—C10	125.2 (2)	C22—C14—H14	107.00
O2—C11—C10	110.3 (2)	C15—C16—H16	120.00
O3—C13—N2	122.22 (18)	C17—C16—H16	120.00
N2—C13—C14	118.95 (18)	C16—C17—H17	120.00
O3—C13—C14	118.83 (18)	C18—C17—H17	120.00
C15—C14—C22	110.04 (15)	C17—C18—H18	120.00
C13—C14—C15	116.70 (16)	C19—C18—H18	120.00
C13—C14—C22	109.53 (15)	C18—C19—H19	120.00
C14—C15—C20	119.04 (16)	C20—C19—H19	120.00
C16—C15—C20	119.08 (18)	N3—C22—H22	107.00
C14—C15—C16	121.85 (18)	C14—C22—H22	107.00
C15—C16—C17	120.9 (2)	C23—C22—H22	107.00
C16—C17—C18	120.0 (2)	C23—C24—H24	126.00
C17—C18—C19	119.8 (2)	C25—C24—H24	126.00
C18—C19—C20	120.3 (2)	C23—C24'—H24'	126.00
C19—C20—C21	119.12 (19)	C25'—C24'—H24'	126.00
C15—C20—C19	119.86 (19)	C24—C25—H25	127.00
C15—C20—C21	120.86 (18)	C26—C25—H25	127.00
O4—C21—C20	121.6 (2)	C24'—C25'—H25'	128.00
N3—C21—C20	116.58 (17)	C26'—C25'—H25'	128.00
O4—C21—N3	121.77 (18)	O5—C26—H26	124.00
C14—C22—C23	112.62 (17)	C25—C26—H26	124.00
N3—C22—C14	110.35 (16)	O5'—C26'—H26'	123.00
N3—C22—C23	113.05 (17)	C25'—C26'—H26'	124.00
O5'—C23—C24'	111.7 (15)	N3—C27—H27B	109.00
C22—C23—C24	130.3 (3)	C28—C27—H27A	109.00
C22—C23—C24'	113.9 (9)	N3—C27—H27A	109.00
O5—C23—C24	110.5 (4)	H27A—C27—H27B	108.00
O5—C23—C22	119.2 (2)	C28—C27—H27B	109.00
O5'—C23—C22	132.8 (12)	C28—C29—H29	120.00
C23—C24—C25	107.6 (5)	C30—C29—H29	120.00
C23—C24'—C25'	108.0 (18)	C29—C30—H30	120.00
C24—C25—C26	105.5 (6)	C31—C30—H30	120.00
C24'—C25'—C26'	104 (2)	C32—C31—H31	120.00
O5—C26—C25	111.6 (7)	C30—C31—H31	120.00
O5'—C26'—C25'	113 (3)	C31—C32—H32	120.00
N3—C27—C28	113.23 (17)	C33—C32—H32	120.00
C27—C28—C33	120.3 (2)	C32—C33—H33	120.00
C29—C28—C33	118.4 (2)	C28—C33—H33	120.00
C27—C28—C29	121.3 (2)
C12—O2—C11—C10	175.0 (3)	N2—C10—C11—O1	−14.8 (4)
C12—O2—C11—O1	−3.2 (4)	N2—C13—C14—C22	−116.6 (2)
C23—O5—C26—C25	3.2 (9)	N2—C13—C14—C15	9.3 (3)
C26—O5—C23—C22	177.2 (4)	O3—C13—C14—C22	62.7 (2)
C26—O5—C23—C24	−4.0 (7)	O3—C13—C14—C15	−171.43 (17)
C8—N1—C1—C6	1.4 (3)	C13—C14—C15—C20	−89.9 (2)
C1—N1—C8—C7	−1.3 (4)	C15—C14—C22—C23	77.8 (2)
C8—N1—C1—C2	−177.0 (4)	C22—C14—C15—C16	−142.20 (18)
C13—N2—C10—C11	−135.0 (2)	C22—C14—C15—C20	35.7 (2)
C10—N2—C13—C14	176.3 (2)	C15—C14—C22—N3	−49.5 (2)
C13—N2—C10—C9	101.6 (3)	C13—C14—C15—C16	92.2 (2)
C10—N2—C13—O3	−3.0 (4)	C13—C14—C22—C23	−152.62 (17)
C27—N3—C21—C20	−172.55 (17)	C13—C14—C22—N3	80.0 (2)
C22—N3—C21—C20	−2.7 (3)	C14—C15—C16—C17	176.68 (19)
C27—N3—C22—C23	78.7 (2)	C20—C15—C16—C17	−1.2 (3)
C21—N3—C22—C23	−91.5 (2)	C16—C15—C20—C19	−0.5 (3)
C21—N3—C22—C14	35.6 (2)	C14—C15—C20—C21	−3.1 (3)
C27—N3—C21—O4	6.2 (3)	C16—C15—C20—C21	174.88 (18)
C27—N3—C22—C14	−154.15 (16)	C14—C15—C20—C19	−178.47 (18)
C22—N3—C27—C28	78.7 (2)	C15—C16—C17—C18	1.6 (3)
C21—N3—C27—C28	−110.7 (2)	C16—C17—C18—C19	−0.1 (3)
C22—N3—C21—O4	176.06 (19)	C17—C18—C19—C20	−1.6 (3)
C2—C1—C6—C7	177.5 (3)	C18—C19—C20—C15	1.9 (3)
C2—C1—C6—C5	−0.2 (5)	C18—C19—C20—C21	−173.54 (19)
N1—C1—C6—C7	−1.0 (3)	C15—C20—C21—O4	165.9 (2)
N1—C1—C6—C5	−178.7 (3)	C19—C20—C21—N3	160.05 (18)
C6—C1—C2—C3	−0.6 (5)	C19—C20—C21—O4	−18.7 (3)
N1—C1—C2—C3	177.5 (4)	C15—C20—C21—N3	−15.4 (3)
C1—C2—C3—C4	0.6 (6)	N3—C22—C23—C24	−104.3 (5)
C2—C3—C4—C5	0.3 (6)	N3—C22—C23—O5	74.3 (3)
C3—C4—C5—C6	−1.1 (6)	C14—C22—C23—C24	129.8 (5)
C4—C5—C6—C1	1.0 (5)	C14—C22—C23—O5	−51.6 (4)
C4—C5—C6—C7	−175.9 (3)	O5—C23—C24—C25	3.3 (7)
C1—C6—C7—C9	−178.5 (3)	C22—C23—C24—C25	−178.0 (4)
C1—C6—C7—C8	0.2 (3)	C23—C24—C25—C26	−1.2 (9)
C5—C6—C7—C8	177.4 (3)	C24—C25—C26—O5	−1.3 (10)
C5—C6—C7—C9	−1.3 (5)	N3—C27—C28—C29	31.7 (3)
C9—C7—C8—N1	179.4 (3)	N3—C27—C28—C33	−149.9 (2)
C6—C7—C8—N1	0.7 (3)	C27—C28—C29—C30	178.6 (3)
C8—C7—C9—C10	98.6 (3)	C33—C28—C29—C30	0.1 (4)
C6—C7—C9—C10	−82.9 (4)	C27—C28—C33—C32	−178.1 (2)
C7—C9—C10—C11	−48.9 (3)	C29—C28—C33—C32	0.4 (4)
C7—C9—C10—N2	73.8 (3)	C28—C29—C30—C31	−0.6 (5)
C9—C10—C11—O2	−67.8 (3)	C29—C30—C31—C32	0.8 (6)
N2—C10—C11—O2	167.1 (2)	C30—C31—C32—C33	−0.3 (5)
C9—C10—C11—O1	110.3 (3)	C31—C32—C33—C28	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.98	2.36	2.751 (3)	103
C22—H22···O3	0.98	2.53	2.959 (2)	106
C27—H27B···O4	0.97	2.33	2.748 (3)	105
N1—H1···O3i	0.86	2.12	2.942 (3)	161
C12—H12A···Cg5ii	0.96	2.63	3.551 (5)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.12	2.942 (3)	161
C12—H12A⋯Cg5ii	0.96	2.63	3.551 (5)	160

Symmetry codes: (i) ; (ii) . Cg5 is the centroid of the C1–C6 ring.