2-Hydr-oxy-16-[(E)-4-hydr-oxy-3-methoxy-benzyl-idene]-13-(4-hydr-oxy-3-methoxy-phen-yl)-11-methyl-1,11-diaza-penta-cyclo-[12.3.1.0.0.0]octa-deca-3(8),4,6-triene-9,15-dione.

In the title compound, C(32)H(30)N(2)O(7), the piperidone ring adopts a chair conformation and the five-membered ring of the dihydro-indenone ring system adopts an envelope conformation. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds occur. The dihedral angle between the two hydr-oxy-subsituted methoxy-phenyl rings is 71.12 (5)°. In the crystal structure, mol-ecules are connected by inter-molecular O-H⋯O hydrogen bonds, forming layers parallel to (001). These layers are further connected by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For details of 1,3-dipolar cyclo­addition, see: Padwa (1984 ▶). For applications of pyrrolidines, see: Dalko & Moisan (2004 ▶); Seayad & List (2005 ▶); Natarajan et al. (2006 ▶); O’Hagan (2000 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C32H30N2O7

M = 554.58

Orthorhombic,

a = 14.7989 (11) Å

b = 15.4918 (11) Å

c = 22.9079 (17) Å

V = 5251.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.39 × 0.39 × 0.31 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.969

130228 measured reflections

9672 independent reflections

7897 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.145

S = 1.09

9672 reflections

385 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017216/is2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017216/is2545Isup2.hkl

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

C32H30N2O7	F(000) = 2336
Mr = 554.58	Dx = 1.403 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9860 reflections
a = 14.7989 (11) Å	θ = 2.3–32.6°
b = 15.4918 (11) Å	µ = 0.10 mm−1
c = 22.9079 (17) Å	T = 100 K
V = 5251.9 (7) Å3	Block, yellow
Z = 8	0.39 × 0.39 × 0.31 mm

Bruker APEXII DUO CCD area-detector diffractometer	9672 independent reflections
Radiation source: fine-focus sealed tube	7897 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 32.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→19
Tmin = 0.962, Tmax = 0.969	k = −23→23
130228 measured reflections	l = −33→34

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0657P)2 + 3.1726P] where P = (Fo2 + 2Fc2)/3
9672 reflections	(Δ/σ)max = 0.001
385 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.30327 (6)	−0.18897 (6)	0.41100 (4)	0.02184 (18)
O2	0.19750 (6)	0.13975 (5)	0.33372 (4)	0.01979 (17)
O3	0.16366 (7)	−0.05592 (6)	0.48344 (4)	0.02408 (19)
O4	−0.17817 (6)	−0.29718 (6)	0.38154 (4)	0.02209 (18)
O5	−0.21109 (7)	−0.28735 (7)	0.27082 (5)	0.0265 (2)
O6	0.62083 (6)	−0.24385 (6)	0.41434 (5)	0.02473 (19)
O7	0.72935 (6)	−0.13939 (6)	0.35393 (4)	0.02204 (18)
N1	0.22581 (7)	0.00074 (6)	0.29585 (4)	0.01670 (18)
N2	0.27389 (7)	0.09389 (6)	0.43104 (4)	0.01600 (17)
C1	0.18714 (8)	−0.08658 (7)	0.28648 (5)	0.0184 (2)
H1A	0.2167	−0.1127	0.2531	0.022*
H1B	0.1235	−0.0807	0.2771	0.022*
C2	0.19647 (8)	−0.14690 (7)	0.33836 (5)	0.0168 (2)
C3	0.27292 (8)	−0.13242 (7)	0.37943 (5)	0.01594 (19)
C4	0.30624 (7)	−0.03950 (7)	0.38134 (5)	0.01382 (18)
C5	0.31885 (8)	−0.00938 (8)	0.31723 (5)	0.0174 (2)
H5A	0.3514	0.0449	0.3155	0.021*
H5B	0.3513	−0.0523	0.2946	0.021*
C6	0.38290 (8)	−0.02131 (7)	0.42424 (5)	0.01551 (19)
H6A	0.3693	−0.0526	0.4604	0.019*
C7	0.37136 (8)	0.07523 (8)	0.43694 (6)	0.0204 (2)
H7A	0.3919	0.0886	0.4761	0.025*
H7B	0.4060	0.1094	0.4094	0.025*
C8	0.22873 (7)	0.02205 (7)	0.40137 (5)	0.01406 (18)
C9	0.18191 (8)	0.05074 (7)	0.34284 (5)	0.01539 (19)
C10	0.08268 (8)	0.03156 (7)	0.35136 (5)	0.0175 (2)
C11	0.01111 (9)	0.04857 (9)	0.31373 (6)	0.0237 (2)
H11A	0.0207	0.0761	0.2782	0.028*
C12	−0.07522 (9)	0.02326 (10)	0.33061 (7)	0.0294 (3)
H12A	−0.1239	0.0349	0.3062	0.035*
C13	−0.09026 (9)	−0.01932 (10)	0.38355 (7)	0.0281 (3)
H13A	−0.1484	−0.0366	0.3935	0.034*
C14	−0.01931 (9)	−0.03585 (8)	0.42110 (6)	0.0223 (2)
H14A	−0.0289	−0.0638	0.4565	0.027*
C15	0.06727 (8)	−0.00943 (7)	0.40453 (5)	0.0174 (2)
C16	0.15262 (8)	−0.02051 (7)	0.43663 (5)	0.0167 (2)
C17	0.13529 (8)	−0.20654 (7)	0.35528 (5)	0.0180 (2)
H17A	0.1508	−0.2383	0.3882	0.022*
C18	0.04812 (8)	−0.22830 (7)	0.32917 (5)	0.0180 (2)
C19	0.02938 (9)	−0.22466 (8)	0.26938 (6)	0.0216 (2)
H19A	0.0746	−0.2094	0.2432	0.026*
C20	−0.05737 (9)	−0.24393 (8)	0.24901 (6)	0.0228 (2)
H20A	−0.0695	−0.2408	0.2092	0.027*
C21	−0.12563 (8)	−0.26768 (8)	0.28732 (5)	0.0197 (2)
C22	−0.10679 (8)	−0.27274 (7)	0.34744 (5)	0.0173 (2)
C23	−0.02099 (8)	−0.25368 (7)	0.36762 (5)	0.0173 (2)
H23A	−0.0088	−0.2577	0.4073	0.021*
C24	−0.15933 (9)	−0.31881 (9)	0.44084 (6)	0.0241 (2)
H24A	−0.2137	−0.3384	0.4594	0.036*
H24B	−0.1369	−0.2688	0.4609	0.036*
H24C	−0.1147	−0.3638	0.4421	0.036*
C25	0.23206 (9)	0.12884 (9)	0.48352 (6)	0.0251 (3)
H25A	0.1692	0.1397	0.4762	0.038*
H25B	0.2615	0.1818	0.4941	0.038*
H25C	0.2379	0.0880	0.5148	0.038*
C26	0.47590 (7)	−0.04947 (7)	0.40435 (5)	0.01503 (19)
C27	0.50398 (8)	−0.13305 (7)	0.41924 (5)	0.0173 (2)
H27A	0.4659	−0.1684	0.4409	0.021*
C28	0.58767 (8)	−0.16339 (7)	0.40201 (5)	0.0175 (2)
C29	0.64600 (8)	−0.11047 (8)	0.36990 (5)	0.0172 (2)
C30	0.61868 (8)	−0.02804 (8)	0.35443 (5)	0.0192 (2)
H30A	0.6569	0.0072	0.3328	0.023*
C31	0.53351 (8)	0.00208 (7)	0.37139 (5)	0.0182 (2)
H31A	0.5152	0.0572	0.3605	0.022*
C32	0.55997 (10)	−0.30334 (9)	0.44075 (7)	0.0302 (3)
H32A	0.5886	−0.3587	0.4441	0.045*
H32B	0.5067	−0.3085	0.4171	0.045*
H32C	0.5436	−0.2829	0.4789	0.045*
H1O5	−0.2099 (15)	−0.3091 (16)	0.2347 (10)	0.044 (6)*
H1O7	0.7311 (17)	−0.1945 (17)	0.3626 (11)	0.052 (7)*
H1O2	0.2281 (16)	0.1577 (16)	0.3664 (11)	0.049 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0183 (4)	0.0159 (4)	0.0313 (5)	0.0002 (3)	−0.0017 (3)	0.0062 (3)
O2	0.0250 (4)	0.0128 (3)	0.0216 (4)	−0.0027 (3)	−0.0060 (3)	0.0032 (3)
O3	0.0225 (4)	0.0266 (4)	0.0231 (4)	0.0019 (3)	0.0039 (3)	0.0080 (3)
O4	0.0167 (4)	0.0276 (4)	0.0219 (4)	0.0001 (3)	0.0013 (3)	0.0012 (3)
O5	0.0192 (4)	0.0359 (5)	0.0242 (4)	−0.0008 (4)	−0.0032 (3)	−0.0094 (4)
O6	0.0202 (4)	0.0180 (4)	0.0360 (5)	0.0060 (3)	0.0009 (4)	0.0064 (4)
O7	0.0148 (4)	0.0233 (4)	0.0280 (4)	0.0034 (3)	0.0026 (3)	0.0001 (3)
N1	0.0174 (4)	0.0166 (4)	0.0160 (4)	−0.0023 (3)	−0.0005 (3)	0.0009 (3)
N2	0.0147 (4)	0.0148 (4)	0.0185 (4)	0.0008 (3)	−0.0015 (3)	−0.0027 (3)
C1	0.0207 (5)	0.0166 (5)	0.0178 (5)	−0.0025 (4)	−0.0009 (4)	−0.0010 (4)
C2	0.0172 (5)	0.0135 (4)	0.0198 (5)	0.0001 (4)	0.0010 (4)	−0.0012 (4)
C3	0.0148 (5)	0.0136 (4)	0.0194 (5)	−0.0003 (3)	0.0020 (4)	0.0006 (4)
C4	0.0131 (4)	0.0125 (4)	0.0159 (4)	0.0000 (3)	0.0006 (3)	0.0009 (3)
C5	0.0164 (5)	0.0189 (5)	0.0170 (5)	−0.0018 (4)	0.0014 (4)	0.0023 (4)
C6	0.0137 (4)	0.0149 (4)	0.0179 (4)	0.0011 (3)	−0.0007 (4)	0.0003 (4)
C7	0.0152 (5)	0.0171 (5)	0.0290 (6)	0.0006 (4)	−0.0022 (4)	−0.0055 (4)
C8	0.0132 (4)	0.0128 (4)	0.0161 (4)	0.0003 (3)	−0.0005 (3)	0.0009 (3)
C9	0.0162 (5)	0.0123 (4)	0.0177 (4)	−0.0015 (3)	−0.0017 (4)	0.0021 (3)
C10	0.0158 (5)	0.0159 (5)	0.0208 (5)	0.0000 (4)	−0.0023 (4)	−0.0021 (4)
C11	0.0196 (5)	0.0277 (6)	0.0238 (5)	0.0008 (4)	−0.0056 (4)	−0.0026 (5)
C12	0.0182 (6)	0.0388 (7)	0.0310 (7)	−0.0002 (5)	−0.0062 (5)	−0.0086 (6)
C13	0.0165 (5)	0.0340 (7)	0.0337 (7)	−0.0048 (5)	0.0012 (5)	−0.0092 (5)
C14	0.0178 (5)	0.0221 (5)	0.0271 (6)	−0.0030 (4)	0.0045 (4)	−0.0041 (4)
C15	0.0150 (5)	0.0153 (4)	0.0221 (5)	0.0003 (4)	0.0015 (4)	−0.0018 (4)
C16	0.0157 (5)	0.0147 (4)	0.0197 (5)	0.0008 (4)	0.0029 (4)	0.0005 (4)
C17	0.0177 (5)	0.0129 (4)	0.0235 (5)	−0.0007 (4)	0.0000 (4)	−0.0009 (4)
C18	0.0181 (5)	0.0135 (4)	0.0224 (5)	−0.0010 (4)	−0.0006 (4)	−0.0011 (4)
C19	0.0229 (6)	0.0205 (5)	0.0212 (5)	−0.0046 (4)	0.0016 (4)	−0.0039 (4)
C20	0.0263 (6)	0.0234 (5)	0.0186 (5)	−0.0029 (5)	−0.0009 (4)	−0.0037 (4)
C21	0.0187 (5)	0.0190 (5)	0.0215 (5)	0.0009 (4)	−0.0025 (4)	−0.0052 (4)
C22	0.0160 (5)	0.0148 (4)	0.0211 (5)	0.0016 (4)	0.0013 (4)	−0.0010 (4)
C23	0.0174 (5)	0.0144 (4)	0.0201 (5)	0.0009 (4)	−0.0011 (4)	−0.0001 (4)
C24	0.0236 (6)	0.0276 (6)	0.0209 (5)	0.0023 (5)	0.0024 (4)	0.0006 (5)
C25	0.0214 (6)	0.0282 (6)	0.0258 (6)	0.0013 (5)	0.0021 (5)	−0.0103 (5)
C26	0.0130 (4)	0.0142 (4)	0.0178 (4)	0.0004 (3)	−0.0005 (4)	0.0003 (3)
C27	0.0144 (5)	0.0158 (4)	0.0217 (5)	0.0007 (4)	−0.0006 (4)	0.0034 (4)
C28	0.0160 (5)	0.0152 (4)	0.0212 (5)	0.0024 (4)	−0.0024 (4)	0.0013 (4)
C29	0.0127 (4)	0.0189 (5)	0.0201 (5)	0.0006 (4)	−0.0007 (4)	−0.0018 (4)
C30	0.0170 (5)	0.0170 (5)	0.0235 (5)	−0.0020 (4)	0.0028 (4)	−0.0002 (4)
C31	0.0172 (5)	0.0136 (4)	0.0237 (5)	−0.0002 (4)	0.0012 (4)	0.0007 (4)
C32	0.0312 (7)	0.0188 (5)	0.0406 (7)	0.0033 (5)	0.0011 (6)	0.0099 (5)

O1—C3	1.2216 (14)	C11—C12	1.391 (2)
O2—C9	1.4137 (13)	C11—H11A	0.9300
O2—H1O2	0.92 (2)	C12—C13	1.398 (2)
O3—C16	1.2154 (15)	C12—H12A	0.9300
O4—C22	1.3674 (15)	C13—C14	1.381 (2)
O4—C24	1.4266 (16)	C13—H13A	0.9300
O5—C21	1.3547 (15)	C14—C15	1.3975 (17)
O5—H1O5	0.89 (2)	C14—H14A	0.9300
O6—C28	1.3690 (14)	C15—C16	1.4717 (17)
O6—C32	1.4235 (17)	C17—C18	1.4613 (16)
O7—C29	1.3624 (14)	C17—H17A	0.9300
O7—H1O7	0.88 (3)	C18—C19	1.3987 (17)
N1—C5	1.4699 (15)	C18—C23	1.4059 (17)
N1—C9	1.4768 (15)	C19—C20	1.3982 (18)
N1—C1	1.4844 (15)	C19—H19A	0.9300
N2—C25	1.4567 (16)	C20—C21	1.3879 (18)
N2—C8	1.4653 (14)	C20—H20A	0.9300
N2—C7	1.4773 (15)	C21—C22	1.4072 (17)
C1—C2	1.5181 (17)	C22—C23	1.3831 (16)
C1—H1A	0.9700	C23—H23A	0.9300
C1—H1B	0.9700	C24—H24A	0.9600
C2—C17	1.3504 (16)	C24—H24B	0.9600
C2—C3	1.4885 (16)	C24—H24C	0.9600
C3—C4	1.5222 (15)	C25—H25A	0.9600
C4—C6	1.5271 (16)	C25—H25B	0.9600
C4—C5	1.5522 (16)	C25—H25C	0.9600
C4—C8	1.5606 (15)	C26—C31	1.3909 (16)
C5—H5A	0.9700	C26—C27	1.4020 (15)
C5—H5B	0.9700	C27—C28	1.3822 (16)
C6—C26	1.5141 (15)	C27—H27A	0.9300
C6—C7	1.5331 (16)	C28—C29	1.3995 (17)
C6—H6A	0.9800	C29—C30	1.3854 (17)
C7—H7A	0.9700	C30—C31	1.3992 (16)
C7—H7B	0.9700	C30—H30A	0.9300
C8—C16	1.5349 (16)	C31—H31A	0.9300
C8—C9	1.5734 (15)	C32—H32A	0.9600
C9—C10	1.5109 (16)	C32—H32B	0.9600
C10—C11	1.3908 (17)	C32—H32C	0.9600
C10—C15	1.3924 (17)
C9—O2—H1O2	104.8 (15)	C14—C13—H13A	119.8
C22—O4—C24	117.27 (10)	C12—C13—H13A	119.8
C21—O5—H1O5	109.0 (14)	C13—C14—C15	118.26 (13)
C28—O6—C32	116.76 (10)	C13—C14—H14A	120.9
C29—O7—H1O7	106.6 (16)	C15—C14—H14A	120.9
C5—N1—C9	103.00 (9)	C10—C15—C14	121.42 (11)
C5—N1—C1	108.19 (9)	C10—C15—C16	110.47 (10)
C9—N1—C1	114.44 (9)	C14—C15—C16	128.10 (11)
C25—N2—C8	118.12 (10)	O3—C16—C15	127.50 (11)
C25—N2—C7	114.33 (10)	O3—C16—C8	124.03 (11)
C8—N2—C7	109.82 (9)	C15—C16—C8	108.47 (9)
N1—C1—C2	114.38 (9)	C2—C17—C18	129.21 (11)
N1—C1—H1A	108.7	C2—C17—H17A	115.4
C2—C1—H1A	108.7	C18—C17—H17A	115.4
N1—C1—H1B	108.7	C19—C18—C23	118.72 (11)
C2—C1—H1B	108.7	C19—C18—C17	124.51 (11)
H1A—C1—H1B	107.6	C23—C18—C17	116.77 (11)
C17—C2—C3	115.55 (10)	C20—C19—C18	120.02 (12)
C17—C2—C1	125.79 (11)	C20—C19—H19A	120.0
C3—C2—C1	118.11 (10)	C18—C19—H19A	120.0
O1—C3—C2	123.06 (10)	C21—C20—C19	120.93 (12)
O1—C3—C4	122.82 (10)	C21—C20—H20A	119.5
C2—C3—C4	114.01 (9)	C19—C20—H20A	119.5
C3—C4—C6	115.70 (9)	O5—C21—C20	124.24 (11)
C3—C4—C5	107.22 (9)	O5—C21—C22	116.47 (11)
C6—C4—C5	117.65 (9)	C20—C21—C22	119.29 (11)
C3—C4—C8	110.37 (9)	O4—C22—C23	125.26 (11)
C6—C4—C8	104.12 (9)	O4—C22—C21	114.93 (11)
C5—C4—C8	100.54 (9)	C23—C22—C21	119.82 (11)
N1—C5—C4	103.58 (9)	C22—C23—C18	121.21 (11)
N1—C5—H5A	111.0	C22—C23—H23A	119.4
C4—C5—H5A	111.0	C18—C23—H23A	119.4
N1—C5—H5B	111.0	O4—C24—H24A	109.5
C4—C5—H5B	111.0	O4—C24—H24B	109.5
H5A—C5—H5B	109.0	H24A—C24—H24B	109.5
C26—C6—C4	115.37 (9)	O4—C24—H24C	109.5
C26—C6—C7	116.08 (9)	H24A—C24—H24C	109.5
C4—C6—C7	102.67 (9)	H24B—C24—H24C	109.5
C26—C6—H6A	107.4	N2—C25—H25A	109.5
C4—C6—H6A	107.4	N2—C25—H25B	109.5
C7—C6—H6A	107.4	H25A—C25—H25B	109.5
N2—C7—C6	106.40 (9)	N2—C25—H25C	109.5
N2—C7—H7A	110.4	H25A—C25—H25C	109.5
C6—C7—H7A	110.4	H25B—C25—H25C	109.5
N2—C7—H7B	110.4	C31—C26—C27	118.73 (10)
C6—C7—H7B	110.4	C31—C26—C6	123.71 (10)
H7A—C7—H7B	108.6	C27—C26—C6	117.54 (10)
N2—C8—C16	114.64 (9)	C28—C27—C26	120.67 (11)
N2—C8—C4	105.38 (9)	C28—C27—H27A	119.7
C16—C8—C4	115.57 (9)	C26—C27—H27A	119.7
N2—C8—C9	112.43 (9)	O6—C28—C27	124.88 (11)
C16—C8—C9	104.28 (9)	O6—C28—C29	114.88 (10)
C4—C8—C9	104.23 (9)	C27—C28—C29	120.23 (10)
O2—C9—N1	109.40 (9)	O7—C29—C30	119.90 (11)
O2—C9—C10	111.68 (9)	O7—C29—C28	120.46 (10)
N1—C9—C10	114.75 (9)	C30—C29—C28	119.64 (11)
O2—C9—C8	109.24 (9)	C29—C30—C31	119.95 (11)
N1—C9—C8	106.22 (9)	C29—C30—H30A	120.0
C10—C9—C8	105.21 (9)	C31—C30—H30A	120.0
C11—C10—C15	120.26 (11)	C26—C31—C30	120.76 (11)
C11—C10—C9	128.52 (11)	C26—C31—H31A	119.6
C15—C10—C9	111.22 (10)	C30—C31—H31A	119.6
C10—C11—C12	118.26 (13)	O6—C32—H32A	109.5
C10—C11—H11A	120.9	O6—C32—H32B	109.5
C12—C11—H11A	120.9	H32A—C32—H32B	109.5
C11—C12—C13	121.34 (13)	O6—C32—H32C	109.5
C11—C12—H12A	119.3	H32A—C32—H32C	109.5
C13—C12—H12A	119.3	H32B—C32—H32C	109.5
C14—C13—C12	120.43 (13)
C5—N1—C1—C2	51.33 (13)	O2—C9—C10—C15	−122.63 (10)
C9—N1—C1—C2	−62.84 (13)	N1—C9—C10—C15	112.13 (11)
N1—C1—C2—C17	144.18 (12)	C8—C9—C10—C15	−4.23 (12)
N1—C1—C2—C3	−26.93 (15)	C15—C10—C11—C12	−0.28 (19)
C17—C2—C3—O1	30.82 (17)	C9—C10—C11—C12	178.73 (12)
C1—C2—C3—O1	−157.16 (11)	C10—C11—C12—C13	−0.9 (2)
C17—C2—C3—C4	−145.65 (10)	C11—C12—C13—C14	1.3 (2)
C1—C2—C3—C4	26.36 (14)	C12—C13—C14—C15	−0.4 (2)
O1—C3—C4—C6	1.84 (16)	C11—C10—C15—C14	1.15 (18)
C2—C3—C4—C6	178.33 (9)	C9—C10—C15—C14	−178.02 (11)
O1—C3—C4—C5	135.34 (12)	C11—C10—C15—C16	179.93 (11)
C2—C3—C4—C5	−48.17 (12)	C9—C10—C15—C16	0.77 (13)
O1—C3—C4—C8	−116.04 (12)	C13—C14—C15—C10	−0.79 (18)
C2—C3—C4—C8	60.45 (12)	C13—C14—C15—C16	−179.35 (12)
C9—N1—C5—C4	47.67 (10)	C10—C15—C16—O3	−177.64 (12)
C1—N1—C5—C4	−73.85 (11)	C14—C15—C16—O3	1.0 (2)
C3—C4—C5—N1	72.33 (11)	C10—C15—C16—C8	3.18 (13)
C6—C4—C5—N1	−155.22 (9)	C14—C15—C16—C8	−178.14 (11)
C8—C4—C5—N1	−43.03 (10)	N2—C8—C16—O3	−61.39 (15)
C3—C4—C6—C26	77.77 (12)	C4—C8—C16—O3	61.50 (15)
C5—C4—C6—C26	−50.77 (13)	C9—C8—C16—O3	175.26 (11)
C8—C4—C6—C26	−160.93 (9)	N2—C8—C16—C15	117.83 (10)
C3—C4—C6—C7	−154.99 (10)	C4—C8—C16—C15	−119.28 (10)
C5—C4—C6—C7	76.47 (12)	C9—C8—C16—C15	−5.52 (11)
C8—C4—C6—C7	−33.69 (11)	C3—C2—C17—C18	171.74 (11)
C25—N2—C7—C6	121.00 (11)	C1—C2—C17—C18	0.4 (2)
C8—N2—C7—C6	−14.46 (13)	C2—C17—C18—C19	33.3 (2)
C26—C6—C7—N2	156.85 (10)	C2—C17—C18—C23	−146.11 (13)
C4—C6—C7—N2	30.06 (12)	C23—C18—C19—C20	1.62 (18)
C25—N2—C8—C16	−12.37 (14)	C17—C18—C19—C20	−177.73 (11)
C7—N2—C8—C16	121.19 (10)	C18—C19—C20—C21	−0.68 (19)
C25—N2—C8—C4	−140.60 (10)	C19—C20—C21—O5	−179.90 (12)
C7—N2—C8—C4	−7.03 (12)	C19—C20—C21—C22	−0.30 (19)
C25—N2—C8—C9	106.50 (12)	C24—O4—C22—C23	−11.19 (17)
C7—N2—C8—C9	−119.94 (10)	C24—O4—C22—C21	168.71 (11)
C3—C4—C8—N2	150.54 (9)	O5—C21—C22—O4	0.03 (16)
C6—C4—C8—N2	25.76 (11)	C20—C21—C22—O4	−179.60 (11)
C5—C4—C8—N2	−96.49 (9)	O5—C21—C22—C23	179.94 (11)
C3—C4—C8—C16	22.88 (13)	C20—C21—C22—C23	0.30 (17)
C6—C4—C8—C16	−101.90 (10)	O4—C22—C23—C18	−179.43 (11)
C5—C4—C8—C16	135.85 (10)	C21—C22—C23—C18	0.67 (17)
C3—C4—C8—C9	−90.91 (10)	C19—C18—C23—C22	−1.63 (17)
C6—C4—C8—C9	144.31 (8)	C17—C18—C23—C22	177.77 (10)
C5—C4—C8—C9	22.07 (10)	C4—C6—C26—C31	88.03 (13)
C5—N1—C9—O2	85.36 (10)	C7—C6—C26—C31	−32.12 (16)
C1—N1—C9—O2	−157.46 (9)	C4—C6—C26—C27	−90.59 (12)
C5—N1—C9—C10	−148.22 (9)	C7—C6—C26—C27	149.25 (11)
C1—N1—C9—C10	−31.04 (13)	C31—C26—C27—C28	0.63 (17)
C5—N1—C9—C8	−32.44 (10)	C6—C26—C27—C28	179.32 (11)
C1—N1—C9—C8	84.75 (11)	C32—O6—C28—C27	7.83 (19)
N2—C8—C9—O2	1.02 (13)	C32—O6—C28—C29	−172.71 (12)
C16—C8—C9—O2	125.80 (10)	C26—C27—C28—O6	−179.88 (11)
C4—C8—C9—O2	−112.59 (10)	C26—C27—C28—C29	0.70 (18)
N2—C8—C9—N1	118.92 (10)	O6—C28—C29—O7	−0.94 (16)
C16—C8—C9—N1	−116.30 (9)	C27—C28—C29—O7	178.54 (11)
C4—C8—C9—N1	5.30 (11)	O6—C28—C29—C30	179.21 (11)
N2—C8—C9—C10	−119.01 (10)	C27—C28—C29—C30	−1.31 (18)
C16—C8—C9—C10	5.77 (11)	O7—C29—C30—C31	−179.27 (11)
C4—C8—C9—C10	127.37 (9)	C28—C29—C30—C31	0.59 (18)
O2—C9—C10—C11	58.29 (16)	C27—C26—C31—C30	−1.36 (18)
N1—C9—C10—C11	−66.94 (16)	C6—C26—C31—C30	−179.97 (11)
C8—C9—C10—C11	176.69 (12)	C29—C30—C31—C26	0.76 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O2i	0.89 (2)	1.77 (2)	2.6554 (14)	173 (2)
O7—H1O7···O4ii	0.88 (3)	2.13 (3)	2.8720 (13)	143 (2)
O2—H1O2···N2	0.92 (3)	1.91 (2)	2.5987 (13)	131 (2)
C1—H1A···O7iii	0.97	2.49	3.3771 (16)	151
C13—H13A···O7iv	0.93	2.57	3.3237 (17)	138
C27—H27A···O1	0.93	2.52	3.0998 (15)	121
C32—H32A···O3v	0.96	2.40	3.1819 (17)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O2i	0.89 (2)	1.77 (2)	2.6554 (14)	173 (2)
O7—H1O7⋯O4ii	0.88 (3)	2.13 (3)	2.8720 (13)	143 (2)
O2—H1O2⋯N2	0.92 (3)	1.91 (2)	2.5987 (13)	131 (2)
C1—H1A⋯O7iii	0.97	2.49	3.3771 (16)	151
C13—H13A⋯O7iv	0.93	2.57	3.3237 (17)	138
C27—H27A⋯O1	0.93	2.52	3.0998 (15)	121
C32—H32A⋯O3v	0.96	2.40	3.1819 (17)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .