rac-(Z)-Methyl 1-benzyl-3-[(3-hy-droxy-quinuclidin-2-yl-idene)meth-yl]-1H-indole-6-carboxyl-ate.

In the title compound, C(25)H(26)N(2)O(3), the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enanti-omers. However, the structure is disordered such that the asymmetric unit contains both enanti-omers in unequal amounts [refined occupancies 0.904 (2) and 0.096 (2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07 (3) °. In the crystal, mol-ecules are linked by O-H⋯O(carbon-yl) hydrogen bonds into chains propagating in [110].

Related literature

For background literature, see: Sekhar et al., (2003 ▶), Amudhan et al., (2010 ▶). For the biological activity of N-benzyl indole quinuclidinone, see: Sonar et al. (2007 ▶). For a similar crystal structure, see: Sonar et al., (2004 ▶).

Experimental

Crystal data

C25H26N2O3

M = 402.48

Triclinic,

a = 6.1619 (1) Å

b = 10.3119 (2) Å

c = 16.5959 (3) Å

α = 75.6705 (7)°

β = 80.0939 (7)°

γ = 85.9410 (7)°

V = 1006.04 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.28 × 0.22 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

9126 measured reflections

4597 independent reflections

3831 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.04

4597 reflections

312 parameters

64 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040731/hg5242sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040731/hg5242Isup2.hkl

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

C25H26N2O3	Z = 2
Mr = 402.48	F(000) = 428
Triclinic, P1	Dx = 1.329 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1619 (1) Å	Cell parameters from 4571 reflections
b = 10.3119 (2) Å	θ = 1.0–27.5°
c = 16.5959 (3) Å	µ = 0.09 mm−1
α = 75.6705 (7)°	T = 90 K
β = 80.0939 (7)°	Block, yellow
γ = 85.9410 (7)°	0.28 × 0.22 × 0.12 mm
V = 1006.04 (3) Å3

Nonius KappaCCD diffractometer	3831 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
Detector resolution: 9.1 pixels mm-1	h = −8→8
ω scans at fixed χ = 55°	k = −13→13
9126 measured reflections	l = −21→21
4597 independent 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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.3522P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4597 reflections	Δρmax = 0.27 e Å−3
312 parameters	Δρmin = −0.20 e Å−3
64 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

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-value wR and goodness of fit S are based on F2. Conventional R-values R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-values based on F2 are statistically about twice as large as those based on F, and R-values based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.31767 (16)	0.66937 (10)	0.24130 (6)	0.0190 (2)
O2	1.05912 (15)	0.90627 (9)	0.09629 (6)	0.0280 (2)
O3	1.17472 (13)	0.78520 (8)	0.00096 (5)	0.0213 (2)
C1	0.1919 (2)	0.56139 (12)	0.24673 (7)	0.0196 (2)
H1	0.0613	0.5379	0.2861	0.024*
C2	0.28163 (19)	0.49219 (11)	0.18719 (7)	0.0181 (2)
C3	0.47803 (19)	0.56153 (11)	0.14234 (7)	0.0172 (2)
C4	0.64453 (19)	0.53937 (11)	0.07749 (7)	0.0180 (2)
H4	0.6356	0.4677	0.0517	0.022*
C5	0.82107 (19)	0.62300 (11)	0.05167 (7)	0.0182 (2)
H5	0.9329	0.6092	0.0072	0.022*
C6	0.83869 (19)	0.72871 (11)	0.08999 (7)	0.0171 (2)
C7	0.67658 (19)	0.75346 (11)	0.15415 (7)	0.0181 (2)
H7	0.6879	0.8245	0.1802	0.022*
C8	0.49701 (19)	0.67018 (11)	0.17875 (7)	0.0171 (2)
C9	1.03202 (19)	0.81587 (11)	0.06408 (7)	0.0184 (2)
C10	1.3663 (2)	0.86728 (12)	−0.02905 (8)	0.0230 (3)
H10A	1.3191	0.9616	−0.0455	0.035*
H10B	1.4539	0.8408	−0.0779	0.035*
H10C	1.4557	0.8552	0.0159	0.035*
C11	0.2901 (2)	0.75327 (12)	0.30102 (8)	0.0212 (3)
H11A	0.1373	0.7463	0.3319	0.025*
H11B	0.3117	0.8477	0.2696	0.025*
C12	0.4496 (2)	0.71600 (12)	0.36448 (7)	0.0196 (3)
C13	0.4619 (2)	0.79843 (13)	0.41841 (8)	0.0248 (3)
H13	0.3700	0.8769	0.4156	0.030*
C14	0.6069 (2)	0.76729 (14)	0.47622 (8)	0.0302 (3)
H14	0.6149	0.8250	0.5122	0.036*
C15	0.7402 (2)	0.65246 (15)	0.48175 (8)	0.0307 (3)
H15	0.8390	0.6309	0.5215	0.037*
C16	0.7282 (2)	0.56959 (14)	0.42883 (8)	0.0300 (3)
H16	0.8186	0.4905	0.4325	0.036*
C17	0.5845 (2)	0.60137 (13)	0.37025 (8)	0.0250 (3)
H17	0.5786	0.5441	0.3338	0.030*
C18	0.2112 (2)	0.36924 (12)	0.17230 (7)	0.0203 (3)
H18	0.2905	0.3426	0.1244	0.024*
C19	0.0490 (3)	0.28894 (14)	0.21750 (9)	0.0190 (3)	0.904 (2)
C20	0.0007 (2)	0.15731 (14)	0.19936 (9)	0.0204 (3)	0.904 (2)
H20	−0.0961	0.1753	0.1550	0.025*	0.904 (2)
O1	0.20291 (17)	0.09447 (10)	0.16992 (7)	0.0268 (3)	0.904 (2)
H1A	0.1766	0.0378	0.1445	0.040*	0.904 (2)
C21	−0.1226 (3)	0.07182 (18)	0.28158 (11)	0.0203 (4)	0.904 (2)
H21	−0.1372	−0.0216	0.2763	0.024*	0.904 (2)
C22	0.0068 (3)	0.07145 (14)	0.35275 (9)	0.0237 (3)	0.904 (2)
H22A	0.1614	0.0414	0.3378	0.028*	0.904 (2)
H22B	−0.0598	0.0092	0.4054	0.028*	0.904 (2)
C23	−0.0005 (3)	0.2159 (2)	0.36551 (10)	0.0232 (3)	0.904 (2)
H23A	−0.0995	0.2201	0.4186	0.028*	0.904 (2)
H23B	0.1488	0.2397	0.3703	0.028*	0.904 (2)
N2	−0.0804 (3)	0.31334 (13)	0.29406 (9)	0.0209 (3)	0.904 (2)
C24	−0.3148 (3)	0.28641 (16)	0.29584 (10)	0.0258 (4)	0.904 (2)
H24A	−0.3657	0.3432	0.2447	0.031*	0.904 (2)
H24B	−0.4054	0.3110	0.3455	0.031*	0.904 (2)
C25	−0.3496 (2)	0.13790 (14)	0.29981 (9)	0.0243 (3)	0.904 (2)
H25A	−0.4259	0.0929	0.3563	0.029*	0.904 (2)
H25B	−0.4408	0.1311	0.2575	0.029*	0.904 (2)
C19'	0.116 (2)	0.2718 (12)	0.2322 (7)	0.013 (3)*	0.096 (2)
C20'	0.080 (3)	0.1336 (14)	0.2189 (9)	0.033 (4)*	0.096 (2)
H20'	0.1935	0.0690	0.2434	0.039*	0.096 (2)
O1'	0.1065 (19)	0.1428 (11)	0.1316 (6)	0.035 (3)*	0.096 (2)
H1'	0.0220	0.0896	0.1222	0.052*	0.096 (2)
C21'	−0.148 (3)	0.0902 (19)	0.2671 (11)	0.039 (5)*	0.096 (2)
H21'	−0.1966	0.0125	0.2494	0.047*	0.096 (2)
C22'	−0.124 (3)	0.0512 (14)	0.3604 (9)	0.036 (4)*	0.096 (2)
H22C	−0.2711	0.0409	0.3964	0.044*	0.096 (2)
H22D	−0.0383	−0.0339	0.3739	0.044*	0.096 (2)
C23'	−0.005 (3)	0.1654 (15)	0.3737 (10)	0.022 (4)*	0.096 (2)
H23C	−0.0666	0.1803	0.4300	0.027*	0.096 (2)
H23D	0.1519	0.1378	0.3743	0.027*	0.096 (2)
N2'	−0.016 (2)	0.2938 (14)	0.3109 (8)	0.021 (3)*	0.096 (2)
C24'	−0.240 (3)	0.3146 (15)	0.2931 (10)	0.022 (4)*	0.096 (2)
H24C	−0.2543	0.4049	0.2558	0.026*	0.096 (2)
H24D	−0.3418	0.3118	0.3465	0.026*	0.096 (2)
C25'	−0.310 (2)	0.2096 (15)	0.2506 (10)	0.036 (4)*	0.096 (2)
H25C	−0.4629	0.1816	0.2752	0.043*	0.096 (2)
H25D	−0.3038	0.2475	0.1893	0.043*	0.096 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0196 (5)	0.0182 (5)	0.0198 (5)	−0.0002 (4)	−0.0017 (4)	−0.0068 (4)
O2	0.0274 (5)	0.0277 (5)	0.0337 (5)	−0.0079 (4)	−0.0019 (4)	−0.0166 (4)
O3	0.0178 (4)	0.0223 (4)	0.0242 (4)	−0.0048 (3)	−0.0004 (3)	−0.0073 (3)
C1	0.0183 (6)	0.0188 (6)	0.0211 (6)	−0.0006 (4)	−0.0034 (5)	−0.0034 (5)
C2	0.0179 (6)	0.0178 (5)	0.0182 (5)	−0.0005 (4)	−0.0045 (4)	−0.0027 (4)
C3	0.0180 (6)	0.0162 (5)	0.0174 (5)	0.0000 (4)	−0.0057 (4)	−0.0023 (4)
C4	0.0208 (6)	0.0173 (5)	0.0177 (5)	−0.0005 (4)	−0.0047 (4)	−0.0061 (4)
C5	0.0176 (6)	0.0194 (6)	0.0182 (5)	0.0007 (4)	−0.0028 (4)	−0.0058 (4)
C6	0.0177 (6)	0.0165 (5)	0.0178 (5)	−0.0008 (4)	−0.0060 (4)	−0.0033 (4)
C7	0.0209 (6)	0.0156 (5)	0.0192 (6)	0.0006 (4)	−0.0063 (5)	−0.0055 (4)
C8	0.0181 (6)	0.0169 (5)	0.0163 (5)	0.0018 (4)	−0.0039 (4)	−0.0038 (4)
C9	0.0186 (6)	0.0181 (6)	0.0194 (6)	0.0008 (4)	−0.0061 (5)	−0.0048 (4)
C10	0.0173 (6)	0.0235 (6)	0.0273 (6)	−0.0051 (5)	−0.0028 (5)	−0.0037 (5)
C11	0.0233 (6)	0.0190 (6)	0.0223 (6)	0.0025 (5)	−0.0014 (5)	−0.0088 (5)
C12	0.0206 (6)	0.0184 (6)	0.0179 (5)	−0.0025 (4)	0.0014 (4)	−0.0034 (4)
C13	0.0289 (7)	0.0210 (6)	0.0245 (6)	−0.0008 (5)	−0.0021 (5)	−0.0070 (5)
C14	0.0375 (8)	0.0316 (7)	0.0244 (7)	−0.0059 (6)	−0.0052 (6)	−0.0106 (5)
C15	0.0287 (7)	0.0395 (8)	0.0236 (6)	−0.0015 (6)	−0.0069 (5)	−0.0052 (6)
C16	0.0288 (7)	0.0320 (7)	0.0263 (7)	0.0078 (6)	−0.0034 (5)	−0.0049 (6)
C17	0.0300 (7)	0.0230 (6)	0.0218 (6)	0.0029 (5)	−0.0030 (5)	−0.0069 (5)
C18	0.0220 (6)	0.0209 (6)	0.0191 (6)	−0.0019 (5)	−0.0033 (5)	−0.0062 (5)
C19	0.0175 (7)	0.0211 (7)	0.0195 (7)	0.0005 (6)	−0.0064 (6)	−0.0048 (5)
C20	0.0179 (7)	0.0246 (7)	0.0207 (7)	−0.0037 (5)	−0.0028 (6)	−0.0082 (5)
O1	0.0232 (5)	0.0290 (6)	0.0325 (6)	−0.0072 (4)	0.0033 (4)	−0.0194 (5)
C21	0.0188 (7)	0.0180 (7)	0.0250 (8)	−0.0030 (5)	−0.0025 (6)	−0.0066 (6)
C22	0.0238 (8)	0.0230 (7)	0.0233 (7)	0.0025 (6)	−0.0058 (6)	−0.0035 (5)
C23	0.0242 (8)	0.0260 (9)	0.0215 (8)	−0.0027 (7)	−0.0035 (5)	−0.0095 (7)
N2	0.0193 (8)	0.0196 (6)	0.0230 (7)	−0.0018 (5)	−0.0001 (6)	−0.0055 (5)
C24	0.0156 (8)	0.0233 (8)	0.0344 (9)	0.0021 (6)	−0.0008 (6)	−0.0025 (6)
C25	0.0174 (7)	0.0251 (7)	0.0302 (8)	−0.0037 (5)	−0.0030 (5)	−0.0059 (6)

N1—C1	1.3772 (15)	C19—C20	1.5204 (18)
N1—C8	1.3787 (15)	C20—O1	1.4296 (18)
N1—C11	1.4510 (15)	C20—C21	1.536 (2)
O2—C9	1.2174 (14)	C20—H20	1.0000
O3—C9	1.3334 (14)	O1—H1A	0.8400
O3—C10	1.4450 (14)	C21—C25	1.528 (2)
C1—C2	1.3771 (17)	C21—C22	1.533 (2)
C1—H1	0.9500	C21—H21	1.0000
C2—C3	1.4419 (16)	C22—C23	1.552 (2)
C2—C18	1.4583 (16)	C22—H22A	0.9900
C3—C4	1.4042 (16)	C22—H22B	0.9900
C3—C8	1.4185 (15)	C23—N2	1.483 (2)
C4—C5	1.3784 (16)	C23—H23A	0.9900
C4—H4	0.9500	C23—H23B	0.9900
C5—C6	1.4100 (15)	N2—C24	1.484 (2)
C5—H5	0.9500	C24—C25	1.545 (2)
C6—C7	1.3890 (16)	C24—H24A	0.9900
C6—C9	1.4819 (16)	C24—H24B	0.9900
C7—C8	1.3907 (16)	C25—H25A	0.9900
C7—H7	0.9500	C25—H25B	0.9900
C10—H10A	0.9800	C19'—N2'	1.473 (13)
C10—H10B	0.9800	C19'—C20'	1.532 (14)
C10—H10C	0.9800	C20'—O1'	1.410 (14)
C11—C12	1.5245 (17)	C20'—C21'	1.525 (16)
C11—H11A	0.9900	C20'—H20'	1.0000
C11—H11B	0.9900	O1'—H1'	0.8400
C12—C17	1.3894 (17)	C21'—C22'	1.530 (16)
C12—C13	1.3924 (17)	C21'—C25'	1.534 (16)
C13—C14	1.3871 (19)	C21'—H21'	1.0000
C13—H13	0.9500	C22'—C23'	1.511 (15)
C14—C15	1.386 (2)	C22'—H22C	0.9900
C14—H14	0.9500	C22'—H22D	0.9900
C15—C16	1.382 (2)	C23'—N2'	1.474 (14)
C15—H15	0.9500	C23'—H23C	0.9900
C16—C17	1.3906 (18)	C23'—H23D	0.9900
C16—H16	0.9500	N2'—C24'	1.449 (14)
C17—H17	0.9500	C24'—C25'	1.552 (15)
C18—C19'	1.317 (11)	C24'—H24C	0.9900
C18—C19	1.3414 (18)	C24'—H24D	0.9900
C18—H18	0.9500	C25'—H25C	0.9900
C19—N2	1.4473 (17)	C25'—H25D	0.9900
C1—N1—C8	108.58 (10)	C25—C21—C20	107.91 (15)
C1—N1—C11	125.67 (10)	C22—C21—C20	108.15 (13)
C8—N1—C11	124.84 (10)	C25—C21—H21	110.5
C9—O3—C10	116.16 (9)	C22—C21—H21	110.5
C2—C1—N1	110.67 (11)	C20—C21—H21	110.5
C2—C1—H1	124.7	C21—C22—C23	108.31 (12)
N1—C1—H1	124.7	C21—C22—H22A	110.0
C1—C2—C3	105.81 (10)	C23—C22—H22A	110.0
C1—C2—C18	129.80 (11)	C21—C22—H22B	110.0
C3—C2—C18	124.28 (11)	C23—C22—H22B	110.0
C4—C3—C8	118.63 (10)	H22A—C22—H22B	108.4
C4—C3—C2	134.05 (11)	N2—C23—C22	110.86 (12)
C8—C3—C2	107.24 (10)	N2—C23—H23A	109.5
C5—C4—C3	119.14 (10)	C22—C23—H23A	109.5
C5—C4—H4	120.4	N2—C23—H23B	109.5
C3—C4—H4	120.4	C22—C23—H23B	109.5
C4—C5—C6	121.22 (11)	H23A—C23—H23B	108.1
C4—C5—H5	119.4	C19—N2—C23	107.06 (13)
C6—C5—H5	119.4	C19—N2—C24	109.12 (13)
C7—C6—C5	121.04 (10)	C23—N2—C24	108.13 (12)
C7—C6—C9	117.76 (10)	N2—C24—C25	112.14 (12)
C5—C6—C9	121.20 (10)	N2—C24—H24A	109.2
C6—C7—C8	117.38 (10)	C25—C24—H24A	109.2
C6—C7—H7	121.3	N2—C24—H24B	109.2
C8—C7—H7	121.3	C25—C24—H24B	109.2
N1—C8—C7	129.70 (10)	H24A—C24—H24B	107.9
N1—C8—C3	107.67 (10)	C21—C25—C24	107.59 (12)
C7—C8—C3	122.56 (11)	C21—C25—H25A	110.2
O2—C9—O3	123.10 (11)	C24—C25—H25A	110.2
O2—C9—C6	124.16 (11)	C21—C25—H25B	110.2
O3—C9—C6	112.74 (9)	C24—C25—H25B	110.2
O3—C10—H10A	109.5	H25A—C25—H25B	108.5
O3—C10—H10B	109.5	C18—C19'—N2'	123.0 (10)
H10A—C10—H10B	109.5	C18—C19'—C20'	123.3 (9)
O3—C10—H10C	109.5	N2'—C19'—C20'	112.0 (9)
H10A—C10—H10C	109.5	O1'—C20'—C21'	114.7 (13)
H10B—C10—H10C	109.5	O1'—C20'—C19'	108.5 (11)
N1—C11—C12	113.36 (10)	C21'—C20'—C19'	107.0 (12)
N1—C11—H11A	108.9	O1'—C20'—H20'	108.8
C12—C11—H11A	108.9	C21'—C20'—H20'	108.8
N1—C11—H11B	108.9	C19'—C20'—H20'	108.8
C12—C11—H11B	108.9	C20'—O1'—H1'	109.5
H11A—C11—H11B	107.7	C20'—C21'—C22'	106.2 (13)
C17—C12—C13	118.55 (11)	C20'—C21'—C25'	108.6 (14)
C17—C12—C11	121.83 (11)	C22'—C21'—C25'	109.8 (14)
C13—C12—C11	119.62 (11)	C20'—C21'—H21'	110.7
C14—C13—C12	120.72 (12)	C22'—C21'—H21'	110.7
C14—C13—H13	119.6	C25'—C21'—H21'	110.7
C12—C13—H13	119.6	C23'—C22'—C21'	104.9 (12)
C15—C14—C13	120.31 (12)	C23'—C22'—H22C	110.8
C15—C14—H14	119.8	C21'—C22'—H22C	110.8
C13—C14—H14	119.8	C23'—C22'—H22D	110.8
C16—C15—C14	119.39 (12)	C21'—C22'—H22D	110.8
C16—C15—H15	120.3	H22C—C22'—H22D	108.8
C14—C15—H15	120.3	N2'—C23'—C22'	116.0 (12)
C15—C16—C17	120.38 (13)	N2'—C23'—H23C	108.3
C15—C16—H16	119.8	C22'—C23'—H23C	108.3
C17—C16—H16	119.8	N2'—C23'—H23D	108.3
C12—C17—C16	120.65 (12)	C22'—C23'—H23D	108.3
C12—C17—H17	119.7	H23C—C23'—H23D	107.4
C16—C17—H17	119.7	C24'—N2'—C23'	107.8 (12)
C19'—C18—C2	123.8 (5)	C24'—N2'—C19'	104.4 (11)
C19—C18—C2	128.40 (12)	C23'—N2'—C19'	105.6 (11)
C19'—C18—H18	115.1	N2'—C24'—C25'	113.8 (11)
C19—C18—H18	115.8	N2'—C24'—H24C	108.8
C2—C18—H18	115.8	C25'—C24'—H24C	108.8
C18—C19—N2	122.23 (12)	N2'—C24'—H24D	108.8
C18—C19—C20	123.71 (12)	C25'—C24'—H24D	108.8
N2—C19—C20	113.72 (11)	H24C—C24'—H24D	107.7
O1—C20—C19	109.43 (11)	C21'—C25'—C24'	106.2 (12)
O1—C20—C21	112.52 (13)	C21'—C25'—H25C	110.5
C19—C20—C21	106.93 (11)	C24'—C25'—H25C	110.5
O1—C20—H20	109.3	C21'—C25'—H25D	110.5
C19—C20—H20	109.3	C24'—C25'—H25D	110.5
C21—C20—H20	109.3	H25C—C25'—H25D	108.7
C25—C21—C22	109.07 (13)
C8—N1—C1—C2	−1.61 (13)	C2—C18—C19—C20	−175.48 (13)
C11—N1—C1—C2	−171.05 (10)	C18—C19—C20—O1	35.0 (2)
N1—C1—C2—C3	0.62 (13)	N2—C19—C20—O1	−138.42 (14)
N1—C1—C2—C18	176.88 (11)	C18—C19—C20—C21	157.16 (17)
C1—C2—C3—C4	177.33 (12)	N2—C19—C20—C21	−16.29 (19)
C18—C2—C3—C4	0.8 (2)	O1—C20—C21—C25	−171.58 (11)
C1—C2—C3—C8	0.56 (12)	C19—C20—C21—C25	68.25 (16)
C18—C2—C3—C8	−175.96 (10)	O1—C20—C21—C22	70.56 (15)
C8—C3—C4—C5	0.38 (16)	C19—C20—C21—C22	−49.60 (17)
C2—C3—C4—C5	−176.11 (12)	C25—C21—C22—C23	−51.32 (16)
C3—C4—C5—C6	0.94 (17)	C20—C21—C22—C23	65.79 (16)
C4—C5—C6—C7	−1.10 (17)	C21—C22—C23—N2	−13.47 (17)
C4—C5—C6—C9	178.01 (11)	C18—C19—N2—C23	−104.06 (18)
C5—C6—C7—C8	−0.11 (16)	C20—C19—N2—C23	69.50 (18)
C9—C6—C7—C8	−179.26 (10)	C18—C19—N2—C24	139.14 (17)
C1—N1—C8—C7	−175.07 (12)	C20—C19—N2—C24	−47.30 (18)
C11—N1—C8—C7	−5.52 (19)	C22—C23—N2—C19	−50.65 (16)
C1—N1—C8—C3	1.92 (12)	C22—C23—N2—C24	66.81 (15)
C11—N1—C8—C3	171.47 (10)	C19—N2—C24—C25	64.01 (16)
C6—C7—C8—N1	178.07 (11)	C23—N2—C24—C25	−52.12 (16)
C6—C7—C8—C3	1.47 (16)	C22—C21—C25—C24	65.38 (16)
C4—C3—C8—N1	−178.88 (10)	C20—C21—C25—C24	−51.89 (16)
C2—C3—C8—N1	−1.52 (12)	N2—C24—C25—C21	−12.01 (18)
C4—C3—C8—C7	−1.63 (17)	C19—C18—C19'—N2'	−82.4 (17)
C2—C3—C8—C7	175.73 (10)	C2—C18—C19'—N2'	27.3 (16)
C10—O3—C9—O2	−0.86 (16)	C19—C18—C19'—C20'	81.5 (17)
C10—O3—C9—C6	178.94 (9)	C2—C18—C19'—C20'	−168.7 (10)
C7—C6—C9—O2	1.15 (17)	C18—C19'—C20'—O1'	−16.1 (19)
C5—C6—C9—O2	−177.99 (11)	N2'—C19'—C20'—O1'	149.4 (13)
C7—C6—C9—O3	−178.65 (10)	C18—C19'—C20'—C21'	−140.4 (14)
C5—C6—C9—O3	2.21 (15)	N2'—C19'—C20'—C21'	25.1 (17)
C1—N1—C11—C12	98.55 (13)	O1'—C20'—C21'—C22'	165.5 (13)
C8—N1—C11—C12	−69.23 (14)	C19'—C20'—C21'—C22'	−74.1 (15)
N1—C11—C12—C17	−8.29 (16)	O1'—C20'—C21'—C25'	−76.4 (17)
N1—C11—C12—C13	171.63 (11)	C19'—C20'—C21'—C25'	44.0 (16)
C17—C12—C13—C14	0.46 (19)	C20'—C21'—C22'—C23'	48.1 (17)
C11—C12—C13—C14	−179.46 (12)	C25'—C21'—C22'—C23'	−69.2 (17)
C12—C13—C14—C15	−0.7 (2)	C21'—C22'—C23'—N2'	21 (2)
C13—C14—C15—C16	0.3 (2)	C22'—C23'—N2'—C24'	42.2 (18)
C14—C15—C16—C17	0.3 (2)	C22'—C23'—N2'—C19'	−68.9 (17)
C13—C12—C17—C16	0.21 (19)	C18—C19'—N2'—C24'	92.0 (15)
C11—C12—C17—C16	−179.87 (12)	C20'—C19'—N2'—C24'	−73.5 (15)
C15—C16—C17—C12	−0.6 (2)	C18—C19'—N2'—C23'	−154.4 (13)
C1—C2—C18—C19'	−32.0 (8)	C20'—C19'—N2'—C23'	40.0 (15)
C3—C2—C18—C19'	143.6 (8)	C23'—N2'—C24'—C25'	−64.7 (16)
C1—C2—C18—C19	−5.1 (2)	C19'—N2'—C24'—C25'	47.2 (16)
C3—C2—C18—C19	170.57 (14)	C20'—C21'—C25'—C24'	−67.2 (16)
C19'—C18—C19—N2	83.7 (14)	C22'—C21'—C25'—C24'	48.5 (17)
C2—C18—C19—N2	−2.6 (2)	N2'—C24'—C25'—C21'	18.4 (18)
C19'—C18—C19—C20	−89.2 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.84	1.97	2.7989 (13)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.84	1.97	2.7989 (13)	169

Symmetry code: (i) .