(S)-tert-Butyl 3-(3-phenyl-1,2,4-oxa-diazol-5-yl)piperidine-1-carboxyl-ate.

The title compound, C(18)H(23)N(3)O(3), crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The phenyl ring and the 1,2,4-oxadiazole ring are inclined to one another by 19.9 (3)° in mol-ecule A and 7.3 (3)° in mol-ecule B. The absolute structure of the title compound was referred to the transfered chiral center (S) of one of the starting reacta-nts. In the crystal, A mol-ecules are linked by C-H⋯N inter-actions involving the two oxadiazole N atoms.

Related literature

For the oxadiazole nucleus as a core structural unit of various muscarinic agonists, see: Orlek & Blaney (1991 ▶). For benzodiazepine receptor partial agonists, see: Watjen & Baker (1989 ▶). For dopamine transporters, see: Gray & Abrahm (1993 ▶). For 5-HT agonists, see: Swain & Baker (1991 ▶). For inhibitors of HIV, see: Matthew et al. (2007 ▶). For GABAA receptor agonists, see: Michaela & Holger (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H23N3O3

M = 329.39

Monoclinic,

a = 6.464 (3) Å

b = 15.515 (8) Å

c = 17.847 (9) Å

β = 99.880 (7)°

V = 1763.2 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.24 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.980, T max = 0.990

7378 measured reflections

3258 independent reflections

2520 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.198

S = 1.01

3258 reflections

440 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018714/su2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018714/su2175Isup2.hkl

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

C18H23N3O3	F(000) = 704
Mr = 329.39	Dx = 1.241 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 818 reflections
a = 6.464 (3) Å	θ = 2.7–23.3°
b = 15.515 (8) Å	µ = 0.09 mm−1
c = 17.847 (9) Å	T = 293 K
β = 99.880 (7)°	Rod, colourless
V = 1763.2 (15) Å3	0.24 × 0.15 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3258 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
graphite	Rint = 0.073
phi and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −7→7
Tmin = 0.980, Tmax = 0.990	k = −18→16
7378 measured reflections	l = −21→14

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)] = 0.073	H-atom parameters constrained
wR(F2) = 0.198	w = 1/[σ2(Fo2) + (0.1416P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3258 reflections	Δρmax = 0.29 e Å−3
440 parameters	Δρmin = −0.44 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (4)

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 esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.4355 (6)	0.9886 (3)	0.68689 (18)	0.0605 (12)
O2	1.1738 (6)	0.7663 (3)	0.79331 (18)	0.0644 (15)
O3	1.2986 (7)	0.7271 (3)	0.6870 (2)	0.0747 (16)
N1	0.5574 (6)	0.9308 (3)	0.7976 (2)	0.0536 (14)
N2	0.3265 (7)	1.0282 (3)	0.7402 (2)	0.0603 (17)
N3	1.0660 (7)	0.8361 (3)	0.6855 (2)	0.0626 (16)
C1	0.3287 (8)	1.0093 (3)	0.8751 (3)	0.0524 (19)
C2	0.1341 (9)	1.0467 (4)	0.8740 (3)	0.062 (2)
C3	0.0626 (11)	1.0639 (4)	0.9411 (3)	0.070 (2)
C4	0.1837 (11)	1.0425 (4)	1.0097 (3)	0.072 (2)
C5	0.3769 (12)	1.0042 (4)	1.0113 (3)	0.079 (2)
C6	0.4488 (9)	0.9868 (4)	0.9447 (3)	0.067 (2)
C7	0.4026 (7)	0.9904 (3)	0.8048 (3)	0.0496 (17)
C8	0.5670 (7)	0.9310 (3)	0.7267 (3)	0.0496 (17)
C9	0.6996 (8)	0.8775 (4)	0.6851 (3)	0.0529 (17)
C10	0.6740 (9)	0.8942 (5)	0.6013 (3)	0.068 (2)
C11	0.8260 (9)	0.8384 (5)	0.5657 (3)	0.067 (2)
C12	1.0481 (9)	0.8513 (4)	0.6046 (3)	0.061 (2)
C13	0.9262 (8)	0.8882 (4)	0.7234 (2)	0.0584 (18)
C14	1.1864 (8)	0.7715 (4)	0.7210 (3)	0.0542 (17)
C15	1.2965 (10)	0.7014 (4)	0.8439 (3)	0.067 (2)
C16	1.2285 (14)	0.7220 (6)	0.9186 (3)	0.106 (3)
C17	1.2262 (15)	0.6118 (5)	0.8167 (4)	0.102 (3)
C18	1.5243 (11)	0.7145 (5)	0.8480 (4)	0.086 (3)
O4	0.6093 (6)	0.1946 (3)	0.82130 (18)	0.0652 (13)
O5	−0.2882 (7)	0.4596 (3)	0.8012 (2)	0.0755 (16)
O6	−0.1493 (6)	0.4210 (3)	0.69793 (18)	0.0678 (15)
N4	0.7414 (7)	0.1666 (4)	0.7705 (2)	0.0672 (19)
N5	0.4557 (7)	0.2334 (3)	0.7072 (2)	0.0514 (14)
N6	0.0024 (7)	0.3759 (3)	0.8124 (2)	0.0583 (15)
C19	0.7234 (8)	0.1768 (3)	0.6348 (3)	0.0502 (17)
C20	0.9211 (9)	0.1437 (4)	0.6355 (3)	0.0614 (17)
C21	0.9925 (10)	0.1274 (4)	0.5684 (3)	0.072 (2)
C22	0.8669 (11)	0.1471 (4)	0.4995 (3)	0.075 (3)
C23	0.6724 (10)	0.1798 (4)	0.4977 (3)	0.070 (2)
C24	0.5980 (9)	0.1963 (4)	0.5641 (3)	0.0617 (19)
C25	0.6435 (8)	0.1934 (3)	0.7043 (2)	0.0489 (17)
C26	0.4423 (8)	0.2318 (3)	0.7778 (3)	0.0500 (16)
C27	0.2658 (9)	0.2633 (3)	0.8154 (3)	0.0514 (16)
C28	0.3205 (9)	0.2705 (4)	0.9012 (3)	0.0626 (19)
C29	0.1270 (10)	0.2999 (4)	0.9314 (3)	0.069 (2)
C30	0.0361 (10)	0.3818 (4)	0.8946 (3)	0.0642 (19)
C31	0.1823 (9)	0.3471 (4)	0.7790 (3)	0.0569 (19)
C32	−0.1542 (9)	0.4222 (4)	0.7715 (3)	0.0570 (19)
C33	−0.2846 (9)	0.4763 (4)	0.6425 (3)	0.0621 (19)
C34	−0.2377 (13)	0.5693 (5)	0.6619 (4)	0.088 (3)
C35	−0.2098 (11)	0.4529 (5)	0.5692 (3)	0.083 (3)
C36	−0.5115 (10)	0.4536 (5)	0.6379 (4)	0.081 (3)
H2A	0.05080	1.06050	0.82770	0.0740*
H3A	−0.06750	1.08990	0.93990	0.0850*
H4A	0.13540	1.05380	1.05490	0.0870*
H5A	0.45900	0.99000	1.05770	0.0950*
H6A	0.57800	0.95980	0.94620	0.0800*
H9A	0.66130	0.81720	0.69160	0.0640*
H10A	0.70080	0.95460	0.59260	0.0820*
H10B	0.53080	0.88150	0.57760	0.0820*
H11A	0.78820	0.77820	0.56920	0.0800*
H11B	0.81450	0.85280	0.51230	0.0800*
H12A	1.13950	0.81190	0.58350	0.0730*
H12B	1.09210	0.90970	0.59590	0.0730*
H13A	0.96590	0.94840	0.72190	0.0700*
H13B	0.94070	0.87100	0.77630	0.0700*
H16A	1.26510	0.78050	0.93250	0.1590*
H16B	1.29790	0.68390	0.95720	0.1590*
H16C	1.07920	0.71480	0.91360	0.1590*
H17A	1.26240	0.60190	0.76740	0.1530*
H17B	1.07690	0.60700	0.81350	0.1530*
H17C	1.29500	0.56980	0.85190	0.1530*
H18A	1.55570	0.77500	0.85240	0.1300*
H18B	1.56650	0.69220	0.80270	0.1300*
H18C	1.59900	0.68480	0.89160	0.1300*
H20A	1.00750	0.13220	0.68170	0.0740*
H21A	1.12460	0.10330	0.56930	0.0860*
H22A	0.91670	0.13770	0.45430	0.0900*
H23A	0.58780	0.19140	0.45120	0.0840*
H24A	0.46540	0.22030	0.56240	0.0740*
H27A	0.15230	0.22090	0.80430	0.0620*
H28A	0.36690	0.21510	0.92300	0.0750*
H28B	0.43330	0.31180	0.91510	0.0750*
H29A	0.02150	0.25480	0.92260	0.0830*
H29B	0.16320	0.30870	0.98580	0.0830*
H30A	−0.09650	0.39390	0.91100	0.0770*
H30B	0.13090	0.42930	0.91090	0.0770*
H31A	0.29170	0.39050	0.78690	0.0680*
H31B	0.13950	0.33890	0.72460	0.0680*
H34A	−0.29080	0.58380	0.70740	0.1320*
H34B	−0.30370	0.60510	0.62080	0.1320*
H34C	−0.08860	0.57840	0.67010	0.1320*
H35A	−0.06140	0.46290	0.57470	0.1240*
H35B	−0.28190	0.48780	0.52850	0.1240*
H35C	−0.23880	0.39320	0.55790	0.1240*
H36A	−0.55900	0.47250	0.68330	0.1220*
H36B	−0.52850	0.39230	0.63280	0.1220*
H36C	−0.59270	0.48150	0.59450	0.1220*

	U11	U22	U33	U12	U13	U23
O1	0.058 (2)	0.070 (2)	0.052 (2)	0.0050 (18)	0.0049 (16)	0.0100 (17)
O2	0.071 (3)	0.081 (3)	0.0403 (19)	0.015 (2)	0.0071 (16)	0.0061 (17)
O3	0.083 (3)	0.089 (3)	0.053 (2)	0.020 (2)	0.0144 (18)	0.0008 (19)
N1	0.052 (3)	0.056 (2)	0.051 (2)	0.006 (2)	0.0039 (17)	0.0042 (19)
N2	0.052 (3)	0.069 (3)	0.060 (3)	0.008 (2)	0.0096 (19)	0.011 (2)
N3	0.066 (3)	0.085 (3)	0.036 (2)	0.019 (2)	0.0064 (17)	0.002 (2)
C1	0.060 (4)	0.046 (3)	0.050 (3)	−0.004 (2)	0.006 (2)	0.003 (2)
C2	0.055 (4)	0.055 (3)	0.073 (4)	−0.002 (3)	0.007 (2)	0.005 (3)
C3	0.084 (5)	0.056 (3)	0.076 (4)	0.002 (3)	0.028 (3)	−0.005 (3)
C4	0.106 (5)	0.057 (3)	0.059 (3)	−0.010 (3)	0.029 (3)	−0.006 (3)
C5	0.097 (5)	0.078 (4)	0.058 (3)	−0.006 (4)	0.002 (3)	0.000 (3)
C6	0.066 (4)	0.069 (4)	0.062 (3)	0.000 (3)	0.002 (3)	−0.001 (3)
C7	0.035 (3)	0.052 (3)	0.060 (3)	−0.006 (2)	0.003 (2)	0.002 (2)
C8	0.037 (3)	0.055 (3)	0.054 (3)	−0.003 (2)	−0.0004 (19)	0.004 (2)
C9	0.044 (3)	0.058 (3)	0.056 (3)	−0.003 (2)	0.007 (2)	0.001 (2)
C10	0.048 (3)	0.103 (5)	0.048 (3)	−0.003 (3)	−0.007 (2)	0.002 (3)
C11	0.066 (4)	0.097 (4)	0.036 (3)	−0.003 (3)	0.005 (2)	0.002 (3)
C12	0.062 (4)	0.078 (4)	0.044 (3)	0.005 (3)	0.012 (2)	0.008 (2)
C13	0.058 (3)	0.078 (4)	0.037 (2)	0.013 (3)	0.002 (2)	−0.002 (2)
C14	0.057 (3)	0.062 (3)	0.042 (3)	−0.002 (3)	0.004 (2)	−0.001 (2)
C15	0.074 (4)	0.069 (4)	0.053 (3)	0.006 (3)	−0.002 (2)	0.019 (3)
C16	0.128 (7)	0.137 (7)	0.048 (3)	0.004 (6)	0.004 (4)	0.024 (4)
C17	0.127 (7)	0.081 (5)	0.087 (5)	−0.020 (5)	−0.011 (4)	0.022 (4)
C18	0.074 (5)	0.083 (5)	0.093 (4)	0.003 (3)	−0.012 (3)	0.022 (4)
O4	0.052 (2)	0.094 (3)	0.0467 (18)	0.017 (2)	0.0005 (14)	0.0030 (18)
O5	0.079 (3)	0.100 (3)	0.049 (2)	0.026 (2)	0.0150 (19)	0.003 (2)
O6	0.072 (3)	0.090 (3)	0.0415 (18)	0.026 (2)	0.0104 (16)	0.0123 (18)
N4	0.045 (3)	0.099 (4)	0.056 (3)	0.016 (2)	0.0039 (18)	0.004 (2)
N5	0.054 (3)	0.057 (2)	0.042 (2)	0.008 (2)	0.0049 (16)	0.0065 (17)
N6	0.073 (3)	0.067 (3)	0.0359 (19)	0.017 (2)	0.0124 (18)	0.0042 (19)
C19	0.042 (3)	0.053 (3)	0.053 (3)	−0.004 (2)	0.001 (2)	0.002 (2)
C20	0.055 (3)	0.067 (3)	0.061 (3)	0.006 (3)	0.007 (2)	0.003 (3)
C21	0.060 (4)	0.081 (4)	0.075 (4)	0.010 (3)	0.015 (3)	−0.005 (3)
C22	0.083 (5)	0.081 (4)	0.066 (4)	0.002 (3)	0.027 (3)	−0.007 (3)
C23	0.073 (4)	0.080 (4)	0.055 (3)	−0.008 (3)	0.006 (3)	0.001 (3)
C24	0.059 (3)	0.076 (4)	0.048 (3)	0.004 (3)	0.003 (2)	0.004 (3)
C25	0.048 (3)	0.050 (3)	0.046 (3)	−0.003 (2)	0.0002 (19)	0.005 (2)
C26	0.050 (3)	0.051 (3)	0.046 (2)	0.006 (2)	−0.0001 (19)	0.001 (2)
C27	0.060 (3)	0.055 (3)	0.038 (2)	0.007 (2)	0.005 (2)	0.001 (2)
C28	0.071 (4)	0.071 (3)	0.044 (3)	0.010 (3)	0.005 (2)	0.006 (2)
C29	0.089 (4)	0.083 (4)	0.037 (3)	0.014 (3)	0.014 (3)	0.014 (2)
C30	0.084 (4)	0.070 (3)	0.040 (3)	0.007 (3)	0.015 (2)	0.002 (2)
C31	0.064 (4)	0.065 (3)	0.043 (3)	0.011 (2)	0.013 (2)	0.009 (2)
C32	0.070 (4)	0.059 (3)	0.042 (3)	0.009 (3)	0.010 (2)	0.000 (2)
C33	0.069 (4)	0.071 (3)	0.042 (3)	0.006 (3)	−0.003 (2)	0.006 (2)
C34	0.108 (6)	0.076 (4)	0.075 (4)	−0.009 (4)	0.000 (4)	0.008 (3)
C35	0.086 (5)	0.111 (6)	0.048 (3)	0.005 (4)	0.004 (3)	0.007 (3)
C36	0.072 (5)	0.092 (5)	0.073 (4)	−0.002 (3)	−0.006 (3)	0.017 (3)

O1—N2	1.417 (6)	C13—H13A	0.9700
O1—C8	1.349 (6)	C13—H13B	0.9700
O2—C14	1.309 (6)	C16—H16A	0.9600
O2—C15	1.487 (7)	C16—H16B	0.9600
O3—C14	1.233 (7)	C16—H16C	0.9600
O4—C26	1.347 (6)	C17—H17C	0.9600
O4—N4	1.416 (6)	C17—H17A	0.9600
O5—C32	1.235 (7)	C17—H17B	0.9600
O6—C33	1.477 (7)	C18—H18B	0.9600
O6—C32	1.319 (6)	C18—H18C	0.9600
N1—C7	1.385 (6)	C18—H18A	0.9600
N1—C8	1.278 (6)	C19—C20	1.375 (8)
N2—C7	1.312 (6)	C19—C24	1.411 (8)
N3—C13	1.462 (7)	C19—C25	1.446 (7)
N3—C14	1.357 (7)	C20—C21	1.379 (8)
N3—C12	1.448 (6)	C21—C22	1.386 (8)
N4—C25	1.309 (6)	C22—C23	1.351 (10)
N5—C25	1.372 (7)	C23—C24	1.377 (8)
N5—C26	1.278 (6)	C26—C27	1.501 (8)
N6—C31	1.465 (7)	C27—C28	1.515 (8)
N6—C32	1.349 (7)	C27—C31	1.511 (8)
N6—C30	1.449 (6)	C28—C29	1.515 (9)
C1—C7	1.447 (7)	C29—C30	1.503 (9)
C1—C2	1.382 (8)	C33—C34	1.503 (10)
C1—C6	1.392 (8)	C33—C35	1.515 (8)
C2—C3	1.382 (8)	C33—C36	1.497 (9)
C3—C4	1.376 (8)	C20—H20A	0.9300
C4—C5	1.379 (10)	C21—H21A	0.9300
C5—C6	1.375 (8)	C22—H22A	0.9300
C8—C9	1.481 (7)	C23—H23A	0.9300
C9—C13	1.516 (7)	C24—H24A	0.9300
C9—C10	1.499 (8)	C27—H27A	0.9800
C10—C11	1.527 (9)	C28—H28A	0.9700
C11—C12	1.497 (8)	C28—H28B	0.9700
C15—C17	1.516 (10)	C29—H29A	0.9700
C15—C16	1.508 (9)	C29—H29B	0.9700
C15—C18	1.476 (10)	C30—H30A	0.9700
C2—H2A	0.9300	C30—H30B	0.9700
C3—H3A	0.9300	C31—H31A	0.9700
C4—H4A	0.9300	C31—H31B	0.9700
C5—H5A	0.9300	C34—H34A	0.9600
C6—H6A	0.9300	C34—H34B	0.9600
C9—H9A	0.9800	C34—H34C	0.9600
C10—H10A	0.9700	C35—H35A	0.9600
C10—H10B	0.9700	C35—H35B	0.9600
C11—H11A	0.9700	C35—H35C	0.9600
C11—H11B	0.9700	C36—H36A	0.9600
C12—H12B	0.9700	C36—H36B	0.9600
C12—H12A	0.9700	C36—H36C	0.9600
N2—O1—C8	105.9 (3)	H17B—C17—H17C	110.00
C14—O2—C15	121.5 (5)	C15—C18—H18A	109.00
N4—O4—C26	105.9 (4)	C15—C18—H18B	109.00
C32—O6—C33	123.1 (5)	C15—C18—H18C	109.00
C7—N1—C8	104.4 (4)	H18A—C18—H18B	110.00
O1—N2—C7	104.0 (4)	H18A—C18—H18C	109.00
C12—N3—C14	121.8 (5)	H18B—C18—H18C	109.00
C13—N3—C14	122.9 (4)	C20—C19—C24	118.6 (5)
C12—N3—C13	114.9 (4)	C20—C19—C25	121.8 (5)
O4—N4—C25	103.3 (4)	C24—C19—C25	119.6 (5)
C25—N5—C26	103.8 (4)	C19—C20—C21	120.6 (5)
C30—N6—C32	118.9 (5)	C20—C21—C22	119.8 (6)
C31—N6—C32	121.1 (4)	C21—C22—C23	120.3 (5)
C30—N6—C31	116.1 (4)	C22—C23—C24	120.7 (5)
C2—C1—C6	119.0 (5)	C19—C24—C23	119.9 (5)
C2—C1—C7	120.5 (5)	N4—C25—N5	113.8 (4)
C6—C1—C7	120.4 (5)	N4—C25—C19	122.0 (5)
C1—C2—C3	120.5 (5)	N5—C25—C19	124.2 (4)
C2—C3—C4	120.1 (6)	O4—C26—N5	113.2 (5)
C3—C4—C5	119.8 (5)	O4—C26—C27	118.5 (4)
C4—C5—C6	120.4 (5)	N5—C26—C27	128.3 (5)
C1—C6—C5	120.2 (6)	C26—C27—C28	114.4 (5)
N2—C7—C1	122.8 (4)	C26—C27—C31	109.3 (4)
N1—C7—N2	112.7 (4)	C28—C27—C31	112.0 (4)
N1—C7—C1	124.6 (4)	C27—C28—C29	108.5 (5)
O1—C8—N1	113.0 (4)	C28—C29—C30	112.6 (5)
O1—C8—C9	118.3 (4)	N6—C30—C29	111.6 (5)
N1—C8—C9	128.8 (5)	N6—C31—C27	109.7 (4)
C8—C9—C10	115.4 (5)	O5—C32—O6	124.9 (5)
C8—C9—C13	108.1 (4)	O5—C32—N6	122.3 (5)
C10—C9—C13	111.3 (4)	O6—C32—N6	112.8 (5)
C9—C10—C11	110.4 (5)	O6—C33—C34	109.3 (5)
C10—C11—C12	111.4 (5)	O6—C33—C35	101.5 (5)
N3—C12—C11	110.3 (5)	O6—C33—C36	111.2 (5)
N3—C13—C9	110.9 (4)	C34—C33—C35	110.3 (5)
O3—C14—N3	121.4 (5)	C34—C33—C36	113.3 (6)
O2—C14—N3	112.2 (5)	C35—C33—C36	110.6 (5)
O2—C14—O3	126.3 (5)	C19—C20—H20A	120.00
C16—C15—C17	111.1 (6)	C21—C20—H20A	120.00
O2—C15—C18	111.1 (5)	C20—C21—H21A	120.00
O2—C15—C17	109.1 (5)	C22—C21—H21A	120.00
O2—C15—C16	100.8 (5)	C21—C22—H22A	120.00
C16—C15—C18	111.5 (6)	C23—C22—H22A	120.00
C17—C15—C18	112.6 (6)	C22—C23—H23A	120.00
C1—C2—H2A	120.00	C24—C23—H23A	120.00
C3—C2—H2A	120.00	C19—C24—H24A	120.00
C2—C3—H3A	120.00	C23—C24—H24A	120.00
C4—C3—H3A	120.00	C26—C27—H27A	107.00
C3—C4—H4A	120.00	C28—C27—H27A	107.00
C5—C4—H4A	120.00	C31—C27—H27A	107.00
C6—C5—H5A	120.00	C27—C28—H28A	110.00
C4—C5—H5A	120.00	C27—C28—H28B	110.00
C1—C6—H6A	120.00	C29—C28—H28A	110.00
C5—C6—H6A	120.00	C29—C28—H28B	110.00
C13—C9—H9A	107.00	H28A—C28—H28B	108.00
C8—C9—H9A	107.00	C28—C29—H29A	109.00
C10—C9—H9A	107.00	C28—C29—H29B	109.00
C9—C10—H10A	110.00	C30—C29—H29A	109.00
C9—C10—H10B	110.00	C30—C29—H29B	109.00
C11—C10—H10A	110.00	H29A—C29—H29B	108.00
C11—C10—H10B	110.00	N6—C30—H30A	109.00
H10A—C10—H10B	108.00	N6—C30—H30B	109.00
C10—C11—H11A	109.00	C29—C30—H30A	109.00
C10—C11—H11B	109.00	C29—C30—H30B	109.00
C12—C11—H11B	109.00	H30A—C30—H30B	108.00
H11A—C11—H11B	108.00	N6—C31—H31A	110.00
C12—C11—H11A	109.00	N6—C31—H31B	110.00
H12A—C12—H12B	108.00	C27—C31—H31A	110.00
C11—C12—H12B	110.00	C27—C31—H31B	110.00
N3—C12—H12A	110.00	H31A—C31—H31B	108.00
N3—C12—H12B	110.00	C33—C34—H34A	109.00
C11—C12—H12A	110.00	C33—C34—H34B	110.00
N3—C13—H13A	109.00	C33—C34—H34C	110.00
N3—C13—H13B	110.00	H34A—C34—H34B	110.00
C9—C13—H13A	109.00	H34A—C34—H34C	109.00
C9—C13—H13B	109.00	H34B—C34—H34C	110.00
H13A—C13—H13B	108.00	C33—C35—H35A	110.00
C15—C16—H16A	109.00	C33—C35—H35B	109.00
C15—C16—H16B	109.00	C33—C35—H35C	109.00
C15—C16—H16C	110.00	H35A—C35—H35B	109.00
H16B—C16—H16C	110.00	H35A—C35—H35C	109.00
H16A—C16—H16B	109.00	H35B—C35—H35C	109.00
H16A—C16—H16C	109.00	C33—C36—H36A	110.00
H17A—C17—H17C	109.00	C33—C36—H36B	109.00
C15—C17—H17A	109.00	C33—C36—H36C	109.00
C15—C17—H17B	109.00	H36A—C36—H36B	110.00
C15—C17—H17C	109.00	H36A—C36—H36C	109.00
H17A—C17—H17B	109.00	H36B—C36—H36C	109.00
N2—O1—C8—N1	−1.4 (6)	C2—C1—C7—N2	20.5 (8)
N2—O1—C8—C9	178.5 (4)	C6—C1—C2—C3	2.0 (9)
C8—O1—N2—C7	−0.3 (5)	C7—C1—C2—C3	179.3 (5)
C15—O2—C14—O3	−1.6 (9)	C2—C1—C6—C5	−2.0 (9)
C15—O2—C14—N3	−178.6 (5)	C7—C1—C6—C5	−179.4 (5)
C14—O2—C15—C17	−63.1 (7)	C2—C1—C7—N1	−158.8 (5)
C14—O2—C15—C18	61.6 (7)	C6—C1—C7—N2	−162.2 (5)
C14—O2—C15—C16	179.9 (6)	C6—C1—C7—N1	18.5 (8)
N4—O4—C26—C27	176.2 (4)	C1—C2—C3—C4	−1.1 (9)
N4—O4—C26—N5	−2.2 (6)	C2—C3—C4—C5	0.3 (10)
C26—O4—N4—C25	2.7 (6)	C3—C4—C5—C6	−0.4 (10)
C33—O6—C32—N6	−171.1 (5)	C4—C5—C6—C1	1.3 (9)
C32—O6—C33—C36	−65.0 (7)	N1—C8—C9—C10	−179.6 (5)
C32—O6—C33—C34	60.9 (7)	O1—C8—C9—C13	125.9 (5)
C33—O6—C32—O5	10.3 (9)	O1—C8—C9—C10	0.6 (7)
C32—O6—C33—C35	177.4 (5)	N1—C8—C9—C13	−54.3 (7)
C7—N1—C8—O1	2.3 (6)	C8—C9—C10—C11	177.3 (5)
C8—N1—C7—N2	−2.5 (6)	C13—C9—C10—C11	53.6 (7)
C8—N1—C7—C1	176.8 (5)	C8—C9—C13—N3	179.4 (4)
C7—N1—C8—C9	−177.6 (5)	C10—C9—C13—N3	−52.9 (7)
O1—N2—C7—N1	1.7 (5)	C9—C10—C11—C12	−55.1 (7)
O1—N2—C7—C1	−177.7 (4)	C10—C11—C12—N3	54.9 (7)
C13—N3—C14—O3	178.0 (5)	C24—C19—C20—C21	−2.0 (8)
C13—N3—C12—C11	−55.9 (7)	C25—C19—C20—C21	179.1 (5)
C14—N3—C12—C11	117.0 (6)	C20—C19—C24—C23	1.8 (8)
C12—N3—C13—C9	54.8 (6)	C25—C19—C24—C23	−179.3 (5)
C14—N3—C13—C9	−118.0 (5)	C20—C19—C25—N4	−10.0 (8)
C12—N3—C14—O2	−177.1 (5)	C20—C19—C25—N5	173.9 (5)
C12—N3—C14—O3	5.7 (8)	C24—C19—C25—N4	171.1 (5)
C13—N3—C14—O2	−4.8 (7)	C24—C19—C25—N5	−4.9 (8)
O4—N4—C25—N5	−2.4 (6)	C19—C20—C21—C22	2.1 (9)
O4—N4—C25—C19	−178.8 (4)	C20—C21—C22—C23	−2.0 (10)
C26—N5—C25—C19	177.4 (5)	C21—C22—C23—C24	1.8 (10)
C25—N5—C26—O4	0.8 (6)	C22—C23—C24—C19	−1.7 (9)
C26—N5—C25—N4	1.1 (6)	O4—C26—C27—C28	15.2 (7)
C25—N5—C26—C27	−177.4 (5)	O4—C26—C27—C31	141.7 (5)
C32—N6—C30—C29	150.6 (5)	N5—C26—C27—C28	−166.7 (5)
C31—N6—C30—C29	−51.5 (7)	N5—C26—C27—C31	−40.2 (7)
C32—N6—C31—C27	−149.7 (5)	C26—C27—C28—C29	−178.1 (4)
C30—N6—C32—O5	−10.6 (9)	C31—C27—C28—C29	56.8 (6)
C30—N6—C32—O6	170.8 (5)	C26—C27—C31—N6	176.9 (4)
C31—N6—C32—O5	−167.4 (6)	C28—C27—C31—N6	−55.3 (6)
C31—N6—C32—O6	14.0 (8)	C27—C28—C29—C30	−54.6 (6)
C30—N6—C31—C27	52.9 (6)	C28—C29—C30—N6	51.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N2i	0.97	2.61	3.352 (7)	133
C18—H18A···N1i	0.96	2.61	3.490 (9)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N2i	0.97	2.61	3.352 (7)	133
C18—H18A⋯N1i	0.96	2.61	3.490 (9)	153

Symmetry code: (i) .