N,N'-[(8-endo,11-endo-Dihy-droxy-penta-cyclo-[5.4.0.0.0.0]undecane-8,11-di-yl)bis-(methyl-enecarbon-yl)]di-l-phenyl-alanine.

The title compound, C(33)H(36)N(2)O(8), is the first example of a disubstituted peptidic pentacycloundecane (PCU) diol. The structure displays an array of inter- and intra-molecular hydrogen bonding by both amide and alcohol functional groups. This hydrogen-bonding system connects the mol-ecules into a three-dimensional network.

Related literature

For examples of PCU cage structures which exhibit C—C bond lengths that deviate from the norm, see: Flippen-Anderson et al. (1991 ▶); Linden et al. (2005 ▶); Kruger et al. (2005 ▶, 2006 ▶). For analogous PCU cage structures and their packing, see: Kruger et al. (2006); Boyle et al. (2007a ▶,b ▶); Vasquez et al. (2002 ▶); Anderson et al. (2007 ▶). For different cage crystal structures, see: Bott et al. (1998 ▶).

Experimental

Crystal data

C33H36N2O8

M = 588.64

Orthorhombic,

a = 10.6230 (5) Å

b = 14.7773 (6) Å

c = 18.2819 (8) Å

V = 2869.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 100 K

0.33 × 0.28 × 0.18 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.678, T max = 0.875

17910 measured reflections

4968 independent reflections

4892 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.06

4968 reflections

412 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2058 Friedel pairs

Flack parameter: −0.02 (14)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035956/gw2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035956/gw2085Isup2.hkl

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

C33H36N2O8	Dx = 1.362 Mg m−3
Mr = 588.64	Melting point: 414 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54199 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4968 reflections
a = 10.6230 (5) Å	θ = 3.9–67.3°
b = 14.7773 (6) Å	µ = 0.80 mm−1
c = 18.2819 (8) Å	T = 100 K
V = 2869.9 (2) Å3	Needle, colourless
Z = 4	0.33 × 0.28 × 0.18 mm
F(000) = 1248

Bruker Kappa DUO APEXII diffractometer	4968 independent reflections
Radiation source: fine-focus sealed tube	4892 reflections with I > 2σ(I)
graphite	Rint = 0.018
1.2° φ scans and ω scans	θmax = 67.3°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→12
Tmin = 0.678, Tmax = 0.875	k = −17→17
17910 measured reflections	l = −21→21

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.8276P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4968 reflections	Δρmax = 0.63 e Å−3
412 parameters	Δρmin = −0.19 e Å−3
6 restraints	Absolute structure: Flack (1983), 2058 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (14)

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 45 mm; combination of φ and ω scans of 1.2°, 80 s per °, 2 iterations.

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
O1	0.26914 (11)	0.87395 (8)	0.16405 (6)	0.0244 (2)
H1O	0.299 (2)	0.8757 (16)	0.1144 (7)	0.044 (6)*
O2	0.40843 (12)	0.84037 (9)	0.04589 (7)	0.0301 (3)
O3	0.60107 (13)	0.69337 (9)	−0.04532 (7)	0.0347 (3)
O4	0.64015 (15)	0.80350 (9)	−0.12717 (7)	0.0377 (3)
H4O	0.620 (3)	0.7565 (13)	−0.1617 (12)	0.057 (7)*
O5	0.15544 (11)	0.99230 (8)	0.23485 (6)	0.0230 (2)
H5O	0.181 (2)	0.9478 (13)	0.2006 (12)	0.053 (7)*
O6	0.21685 (12)	1.25096 (8)	0.32318 (7)	0.0291 (3)
O7	−0.06852 (12)	1.28739 (9)	0.24885 (7)	0.0317 (3)
O8	0.03196 (12)	1.40531 (8)	0.20026 (7)	0.0314 (3)
H8O	−0.035 (2)	1.4387 (18)	0.2239 (15)	0.072 (9)*
N1	0.61453 (14)	0.81718 (10)	0.06881 (7)	0.0241 (3)
H1N	0.6770 (17)	0.7959 (15)	0.1017 (11)	0.042 (6)*
N2	0.13816 (14)	1.17823 (9)	0.22652 (7)	0.0237 (3)
H2N	0.120 (2)	1.1205 (10)	0.2053 (13)	0.046 (6)*
C1	0.60049 (19)	1.03551 (14)	0.28800 (11)	0.0371 (4)
H1A	0.6632	1.0307	0.3279	0.045*
H1B	0.6278	1.0809	0.2515	0.045*
C2	0.56791 (17)	0.94515 (12)	0.25429 (10)	0.0298 (4)
H2	0.6403	0.9140	0.2300	0.036*
C3	0.45567 (16)	0.96466 (11)	0.20319 (9)	0.0214 (3)
H3	0.4825	0.9846	0.1533	0.026*
C4	0.38679 (15)	0.87291 (11)	0.20250 (9)	0.0220 (3)
C5	0.37308 (16)	0.85663 (11)	0.28471 (9)	0.0248 (3)
H5	0.3493	0.7934	0.2986	0.030*
C6	0.50323 (18)	0.88894 (13)	0.31455 (10)	0.0320 (4)
H6	0.5556	0.8445	0.3424	0.038*
C7	0.46939 (18)	1.05156 (13)	0.31537 (10)	0.0307 (4)
H7	0.4585	1.1100	0.3422	0.037*
C8	0.38393 (16)	1.04175 (11)	0.24716 (9)	0.0218 (3)
H8	0.3765	1.0993	0.2187	0.026*
C9	0.25780 (16)	1.01308 (10)	0.28335 (9)	0.0216 (3)
C10	0.30414 (16)	0.93324 (11)	0.32961 (9)	0.0232 (3)
H10	0.2433	0.9112	0.3674	0.028*
C11	0.43220 (18)	0.96760 (13)	0.36003 (10)	0.0314 (4)
H11	0.4439	0.9695	0.4143	0.038*
C12	0.46489 (16)	0.79656 (11)	0.16772 (9)	0.0256 (4)
H12A	0.5445	0.7888	0.1952	0.031*
H12B	0.4174	0.7390	0.1704	0.031*
C13	0.49385 (16)	0.81869 (11)	0.08861 (9)	0.0236 (3)
C14	0.65210 (17)	0.84505 (12)	−0.00387 (9)	0.0257 (4)
H14	0.5983	0.8978	−0.0179	0.031*
C15	0.62849 (17)	0.77022 (12)	−0.05975 (10)	0.0276 (4)
C16	0.78958 (17)	0.87780 (12)	−0.00307 (10)	0.0289 (4)
H16A	0.8445	0.8295	0.0167	0.035*
H16B	0.8172	0.8913	−0.0536	0.035*
C17	0.80165 (16)	0.96194 (12)	0.04362 (10)	0.0265 (4)
C18	0.85097 (17)	0.95746 (12)	0.11397 (10)	0.0300 (4)
H18	0.8838	0.9018	0.1316	0.036*
C19	0.85280 (18)	1.03328 (13)	0.15874 (11)	0.0323 (4)
H19	0.8856	1.0290	0.2070	0.039*
C20	0.80709 (18)	1.11473 (13)	0.13338 (11)	0.0328 (4)
H20	0.8080	1.1665	0.1641	0.039*
C21	0.76010 (19)	1.12083 (13)	0.06335 (12)	0.0372 (4)
H21	0.7293	1.1770	0.0455	0.045*
C22	0.7578 (2)	1.04459 (13)	0.01874 (11)	0.0357 (4)
H22	0.7256	1.0493	−0.0296	0.043*
C23	0.20364 (16)	1.08852 (11)	0.33230 (9)	0.0243 (3)
H23A	0.1209	1.0686	0.3513	0.029*
H23B	0.2603	1.0970	0.3747	0.029*
C24	0.18689 (15)	1.17912 (11)	0.29397 (9)	0.0219 (3)
C25	0.12644 (16)	1.26173 (11)	0.18574 (9)	0.0235 (3)
H25	0.2069	1.2964	0.1899	0.028*
C26	0.01960 (16)	1.31895 (11)	0.21642 (9)	0.0235 (3)
C27	0.09994 (16)	1.24235 (12)	0.10448 (9)	0.0262 (4)
H27A	0.0140	1.2172	0.0995	0.031*
H27B	0.1032	1.2999	0.0768	0.031*
C28	0.19323 (18)	1.17667 (12)	0.07203 (9)	0.0275 (4)
C29	0.31774 (19)	1.20072 (14)	0.06228 (10)	0.0341 (4)
H29	0.3443	1.2605	0.0737	0.041*
C30	0.4044 (2)	1.13836 (18)	0.03599 (11)	0.0459 (5)
H30	0.4901	1.1552	0.0303	0.055*
C31	0.3659 (2)	1.05186 (16)	0.01803 (11)	0.0469 (6)
H31	0.4250	1.0094	−0.0006	0.056*
C32	0.2418 (2)	1.02721 (14)	0.02720 (10)	0.0416 (5)
H32	0.2151	0.9677	0.0152	0.050*
C33	0.1566 (2)	1.08942 (13)	0.05394 (9)	0.0328 (4)
H33	0.0711	1.0721	0.0601	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0231 (6)	0.0249 (6)	0.0253 (6)	−0.0010 (5)	0.0020 (5)	−0.0041 (5)
O2	0.0264 (6)	0.0355 (7)	0.0285 (6)	0.0043 (5)	−0.0009 (5)	−0.0052 (5)
O3	0.0393 (7)	0.0267 (7)	0.0380 (7)	−0.0044 (6)	0.0108 (6)	−0.0073 (5)
O4	0.0549 (8)	0.0342 (7)	0.0240 (6)	−0.0080 (6)	0.0032 (6)	−0.0060 (5)
O5	0.0231 (6)	0.0207 (6)	0.0254 (6)	0.0004 (4)	−0.0005 (4)	−0.0017 (5)
O6	0.0350 (7)	0.0229 (6)	0.0292 (6)	0.0004 (5)	−0.0051 (5)	−0.0043 (5)
O7	0.0315 (7)	0.0298 (6)	0.0338 (6)	0.0024 (5)	0.0089 (6)	0.0043 (5)
O8	0.0316 (7)	0.0207 (6)	0.0420 (7)	0.0030 (5)	0.0059 (5)	0.0029 (5)
N1	0.0251 (7)	0.0242 (7)	0.0230 (7)	−0.0002 (6)	0.0005 (5)	−0.0011 (6)
N2	0.0285 (7)	0.0196 (7)	0.0230 (7)	0.0009 (6)	−0.0019 (5)	−0.0012 (6)
C1	0.0339 (10)	0.0427 (10)	0.0348 (10)	−0.0041 (9)	−0.0032 (8)	−0.0030 (9)
C2	0.0249 (9)	0.0286 (9)	0.0358 (9)	0.0007 (7)	−0.0038 (7)	0.0017 (7)
C3	0.0225 (8)	0.0206 (7)	0.0210 (8)	−0.0006 (6)	0.0013 (6)	0.0008 (6)
C4	0.0231 (8)	0.0194 (7)	0.0235 (8)	−0.0003 (6)	0.0022 (6)	0.0002 (6)
C5	0.0275 (8)	0.0199 (7)	0.0268 (8)	0.0020 (6)	0.0048 (7)	0.0036 (7)
C6	0.0302 (9)	0.0404 (10)	0.0253 (8)	0.0043 (8)	−0.0007 (7)	0.0044 (8)
C7	0.0309 (9)	0.0382 (10)	0.0230 (8)	−0.0071 (8)	−0.0012 (7)	−0.0032 (8)
C8	0.0264 (8)	0.0178 (7)	0.0212 (7)	−0.0012 (6)	0.0015 (7)	0.0006 (6)
C9	0.0252 (8)	0.0189 (8)	0.0208 (7)	0.0014 (6)	0.0015 (6)	0.0006 (6)
C10	0.0273 (8)	0.0210 (8)	0.0211 (7)	0.0014 (7)	0.0054 (6)	0.0030 (6)
C11	0.0335 (10)	0.0322 (9)	0.0286 (9)	0.0016 (8)	−0.0060 (7)	0.0049 (7)
C12	0.0273 (9)	0.0207 (8)	0.0288 (9)	0.0000 (7)	0.0031 (7)	−0.0011 (7)
C13	0.0260 (8)	0.0183 (7)	0.0266 (8)	−0.0006 (7)	0.0011 (7)	−0.0045 (6)
C14	0.0277 (9)	0.0260 (8)	0.0236 (8)	−0.0016 (7)	0.0016 (7)	−0.0015 (7)
C15	0.0262 (9)	0.0264 (9)	0.0303 (9)	−0.0012 (7)	0.0051 (7)	−0.0040 (7)
C16	0.0276 (9)	0.0297 (9)	0.0294 (9)	−0.0013 (7)	0.0024 (7)	−0.0010 (7)
C17	0.0239 (8)	0.0258 (8)	0.0297 (8)	−0.0047 (7)	0.0052 (7)	0.0008 (7)
C18	0.0270 (9)	0.0276 (9)	0.0354 (9)	−0.0016 (7)	0.0005 (7)	0.0052 (8)
C19	0.0298 (9)	0.0365 (10)	0.0306 (9)	−0.0045 (8)	−0.0027 (8)	−0.0002 (8)
C20	0.0282 (9)	0.0268 (9)	0.0436 (10)	−0.0066 (7)	0.0046 (8)	−0.0066 (8)
C21	0.0360 (10)	0.0244 (9)	0.0512 (12)	−0.0021 (8)	−0.0058 (9)	0.0059 (8)
C22	0.0405 (11)	0.0323 (10)	0.0343 (9)	−0.0064 (8)	−0.0089 (8)	0.0053 (8)
C23	0.0278 (8)	0.0246 (8)	0.0204 (7)	0.0030 (7)	0.0012 (7)	0.0004 (7)
C24	0.0197 (7)	0.0233 (8)	0.0228 (7)	0.0033 (6)	0.0025 (6)	−0.0026 (7)
C25	0.0245 (8)	0.0210 (8)	0.0249 (8)	0.0003 (6)	−0.0002 (7)	0.0010 (7)
C26	0.0265 (8)	0.0237 (8)	0.0202 (7)	0.0001 (7)	−0.0021 (6)	0.0010 (6)
C27	0.0274 (8)	0.0288 (8)	0.0225 (8)	0.0015 (7)	−0.0007 (7)	0.0032 (7)
C28	0.0344 (9)	0.0306 (9)	0.0177 (7)	0.0047 (8)	0.0015 (6)	0.0044 (7)
C29	0.0338 (10)	0.0417 (11)	0.0268 (9)	−0.0012 (8)	0.0027 (7)	0.0031 (8)
C30	0.0336 (10)	0.0732 (16)	0.0308 (10)	0.0105 (11)	0.0078 (8)	0.0135 (10)
C31	0.0612 (15)	0.0535 (13)	0.0259 (9)	0.0258 (11)	0.0061 (9)	0.0050 (9)
C32	0.0649 (14)	0.0374 (11)	0.0225 (8)	0.0111 (10)	−0.0015 (9)	−0.0019 (8)
C33	0.0441 (11)	0.0332 (10)	0.0210 (8)	0.0015 (8)	−0.0001 (7)	0.0007 (7)

O1—C4	1.434 (2)	C10—H10	1.0000
O1—H1O	0.961 (10)	C11—H11	1.0000
O2—C13	1.239 (2)	C12—C13	1.514 (2)
O3—C15	1.202 (2)	C12—H12A	0.9900
O4—C15	1.333 (2)	C12—H12B	0.9900
O4—H4O	0.961 (10)	C14—C15	1.526 (2)
O5—C9	1.436 (2)	C14—C16	1.539 (2)
O5—H5O	0.949 (10)	C14—H14	1.0000
O6—C24	1.230 (2)	C16—C17	1.514 (2)
O7—C26	1.202 (2)	C16—H16A	0.9900
O8—C26	1.316 (2)	C16—H16B	0.9900
O8—H8O	0.968 (10)	C17—C22	1.384 (3)
N1—C13	1.332 (2)	C17—C18	1.390 (3)
N1—C14	1.447 (2)	C18—C19	1.388 (3)
N1—H1N	0.950 (10)	C18—H18	0.9500
N2—C24	1.337 (2)	C19—C20	1.378 (3)
N2—C25	1.447 (2)	C19—H19	0.9500
N2—H2N	0.956 (10)	C20—C21	1.377 (3)
C1—C7	1.499 (3)	C20—H20	0.9500
C1—C2	1.511 (3)	C21—C22	1.391 (3)
C1—H1A	0.9900	C21—H21	0.9500
C1—H1B	0.9900	C22—H22	0.9500
C2—C6	1.541 (3)	C23—C24	1.522 (2)
C2—C3	1.542 (2)	C23—H23A	0.9900
C2—H2	1.0000	C23—H23B	0.9900
C3—C4	1.541 (2)	C25—C26	1.522 (2)
C3—C8	1.589 (2)	C25—C27	1.539 (2)
C3—H3	1.0000	C25—H25	1.0000
C4—C5	1.529 (2)	C27—C28	1.509 (2)
C4—C12	1.538 (2)	C27—H27A	0.9900
C5—C6	1.561 (3)	C27—H27B	0.9900
C5—C10	1.579 (2)	C28—C29	1.381 (3)
C5—H5	1.0000	C28—C33	1.387 (3)
C6—C11	1.616 (3)	C29—C30	1.388 (3)
C6—H6	1.0000	C29—H29	0.9500
C7—C11	1.537 (3)	C30—C31	1.381 (4)
C7—C8	1.549 (2)	C30—H30	0.9500
C7—H7	1.0000	C31—C32	1.378 (4)
C8—C9	1.553 (2)	C31—H31	0.9500
C8—H8	1.0000	C32—C33	1.380 (3)
C9—C10	1.533 (2)	C32—H32	0.9500
C9—C23	1.541 (2)	C33—H33	0.9500
C10—C11	1.555 (3)
C4—O1—H1O	100.1 (15)	C4—C12—H12B	109.6
C15—O4—H4O	108.7 (16)	H12A—C12—H12B	108.1
C9—O5—H5O	109.6 (17)	O2—C13—N1	122.52 (16)
C26—O8—H8O	108.7 (18)	O2—C13—C12	120.59 (15)
C13—N1—C14	120.67 (14)	N1—C13—C12	116.83 (15)
C13—N1—H1N	120.4 (15)	N1—C14—C15	111.29 (14)
C14—N1—H1N	118.9 (15)	N1—C14—C16	110.04 (14)
C24—N2—C25	120.00 (14)	C15—C14—C16	112.97 (14)
C24—N2—H2N	117.4 (15)	N1—C14—H14	107.4
C25—N2—H2N	122.3 (15)	C15—C14—H14	107.4
C7—C1—C2	93.63 (15)	C16—C14—H14	107.4
C7—C1—H1A	113.0	O3—C15—O4	125.04 (17)
C2—C1—H1A	113.0	O3—C15—C14	125.29 (16)
C7—C1—H1B	113.0	O4—C15—C14	109.65 (14)
C2—C1—H1B	113.0	C17—C16—C14	110.13 (14)
H1A—C1—H1B	110.4	C17—C16—H16A	109.6
C1—C2—C6	106.67 (16)	C14—C16—H16A	109.6
C1—C2—C3	105.01 (15)	C17—C16—H16B	109.6
C6—C2—C3	100.90 (14)	C14—C16—H16B	109.6
C1—C2—H2	114.3	H16A—C16—H16B	108.1
C6—C2—H2	114.3	C22—C17—C18	118.22 (17)
C3—C2—H2	114.3	C22—C17—C16	120.73 (16)
C4—C3—C2	101.98 (13)	C18—C17—C16	120.96 (16)
C4—C3—C8	114.03 (13)	C19—C18—C17	120.83 (17)
C2—C3—C8	101.45 (13)	C19—C18—H18	119.6
C4—C3—H3	112.8	C17—C18—H18	119.6
C2—C3—H3	112.8	C20—C19—C18	120.12 (17)
C8—C3—H3	112.8	C20—C19—H19	119.9
O1—C4—C5	113.61 (13)	C18—C19—H19	119.9
O1—C4—C12	105.98 (13)	C21—C20—C19	119.85 (18)
C5—C4—C12	110.02 (13)	C21—C20—H20	120.1
O1—C4—C3	114.11 (13)	C19—C20—H20	120.1
C5—C4—C3	100.11 (13)	C20—C21—C22	119.90 (18)
C12—C4—C3	113.13 (13)	C20—C21—H21	120.1
C4—C5—C6	102.18 (13)	C22—C21—H21	120.1
C4—C5—C10	116.27 (13)	C17—C22—C21	121.07 (17)
C6—C5—C10	90.56 (13)	C17—C22—H22	119.5
C4—C5—H5	114.9	C21—C22—H22	119.5
C6—C5—H5	114.9	C24—C23—C9	114.38 (13)
C10—C5—H5	114.9	C24—C23—H23A	108.7
C2—C6—C5	108.05 (14)	C9—C23—H23A	108.7
C2—C6—C11	100.85 (15)	C24—C23—H23B	108.7
C5—C6—C11	89.21 (13)	C9—C23—H23B	108.7
C2—C6—H6	118.0	H23A—C23—H23B	107.6
C5—C6—H6	118.0	O6—C24—N2	120.59 (15)
C11—C6—H6	118.0	O6—C24—C23	121.95 (14)
C1—C7—C11	106.77 (16)	N2—C24—C23	117.47 (14)
C1—C7—C8	105.12 (15)	N2—C25—C26	110.36 (13)
C11—C7—C8	101.62 (14)	N2—C25—C27	110.76 (13)
C1—C7—H7	114.1	C26—C25—C27	108.83 (13)
C11—C7—H7	114.1	N2—C25—H25	109.0
C8—C7—H7	114.1	C26—C25—H25	109.0
C7—C8—C9	100.84 (13)	C27—C25—H25	109.0
C7—C8—C3	101.14 (13)	O7—C26—O8	124.36 (16)
C9—C8—C3	115.70 (13)	O7—C26—C25	123.14 (15)
C7—C8—H8	112.6	O8—C26—C25	112.42 (14)
C9—C8—H8	112.6	C28—C27—C25	112.28 (14)
C3—C8—H8	112.6	C28—C27—H27A	109.1
O5—C9—C10	114.79 (13)	C25—C27—H27A	109.1
O5—C9—C23	103.32 (13)	C28—C27—H27B	109.1
C10—C9—C23	110.87 (13)	C25—C27—H27B	109.1
O5—C9—C8	116.65 (13)	H27A—C27—H27B	107.9
C10—C9—C8	99.67 (13)	C29—C28—C33	118.50 (18)
C23—C9—C8	111.85 (13)	C29—C28—C27	120.95 (17)
C9—C10—C11	103.12 (13)	C33—C28—C27	120.50 (17)
C9—C10—C5	114.46 (13)	C28—C29—C30	120.6 (2)
C11—C10—C5	90.82 (13)	C28—C29—H29	119.7
C9—C10—H10	115.1	C30—C29—H29	119.7
C11—C10—H10	115.1	C31—C30—C29	120.1 (2)
C5—C10—H10	115.1	C31—C30—H30	120.0
C7—C11—C10	107.37 (14)	C29—C30—H30	120.0
C7—C11—C6	100.80 (14)	C32—C31—C30	119.9 (2)
C10—C11—C6	89.41 (13)	C32—C31—H31	120.1
C7—C11—H11	118.2	C30—C31—H31	120.1
C10—C11—H11	118.2	C31—C32—C33	119.7 (2)
C6—C11—H11	118.2	C31—C32—H32	120.2
C13—C12—C4	110.24 (13)	C33—C32—H32	120.2
C13—C12—H12A	109.6	C32—C33—C28	121.3 (2)
C4—C12—H12A	109.6	C32—C33—H33	119.3
C13—C12—H12B	109.6	C28—C33—H33	119.3
C7—C1—C2—C6	−52.22 (17)	C5—C10—C11—C7	100.82 (14)
C7—C1—C2—C3	54.33 (17)	C9—C10—C11—C6	−115.68 (13)
C1—C2—C3—C4	−152.25 (15)	C5—C10—C11—C6	−0.31 (12)
C6—C2—C3—C4	−41.51 (16)	C2—C6—C11—C7	0.97 (16)
C1—C2—C3—C8	−34.36 (17)	C5—C6—C11—C7	−107.27 (14)
C6—C2—C3—C8	76.38 (15)	C2—C6—C11—C10	108.55 (14)
C2—C3—C4—O1	174.09 (13)	C5—C6—C11—C10	0.31 (12)
C8—C3—C4—O1	65.62 (17)	O1—C4—C12—C13	64.48 (16)
C2—C3—C4—C5	52.38 (15)	C5—C4—C12—C13	−172.31 (14)
C8—C3—C4—C5	−56.08 (16)	C3—C4—C12—C13	−61.28 (18)
C2—C3—C4—C12	−64.64 (17)	C14—N1—C13—O2	2.7 (2)
C8—C3—C4—C12	−173.11 (13)	C14—N1—C13—C12	−174.58 (14)
O1—C4—C5—C6	−162.75 (13)	C4—C12—C13—O2	−51.7 (2)
C12—C4—C5—C6	78.63 (16)	C4—C12—C13—N1	125.61 (16)
C3—C4—C5—C6	−40.69 (15)	C13—N1—C14—C15	−79.26 (19)
O1—C4—C5—C10	−65.99 (18)	C13—N1—C14—C16	154.73 (15)
C12—C4—C5—C10	175.39 (14)	N1—C14—C15—O3	−10.9 (3)
C3—C4—C5—C10	56.07 (17)	C16—C14—C15—O3	113.5 (2)
C1—C2—C6—C5	125.34 (16)	N1—C14—C15—O4	167.77 (15)
C3—C2—C6—C5	15.89 (18)	C16—C14—C15—O4	−67.9 (2)
C1—C2—C6—C11	32.60 (17)	N1—C14—C16—C17	−64.59 (18)
C3—C2—C6—C11	−76.85 (16)	C15—C14—C16—C17	170.36 (14)
C4—C5—C6—C2	15.59 (17)	C14—C16—C17—C22	−74.1 (2)
C10—C5—C6—C2	−101.47 (15)	C14—C16—C17—C18	102.51 (18)
C4—C5—C6—C11	116.75 (13)	C22—C17—C18—C19	1.8 (3)
C10—C5—C6—C11	−0.31 (12)	C16—C17—C18—C19	−174.88 (17)
C2—C1—C7—C11	53.08 (17)	C17—C18—C19—C20	−1.0 (3)
C2—C1—C7—C8	−54.34 (17)	C18—C19—C20—C21	−0.3 (3)
C1—C7—C8—C9	153.91 (15)	C19—C20—C21—C22	0.6 (3)
C11—C7—C8—C9	42.77 (16)	C18—C17—C22—C21	−1.5 (3)
C1—C7—C8—C3	34.72 (17)	C16—C17—C22—C21	175.23 (17)
C11—C7—C8—C3	−76.42 (15)	C20—C21—C22—C17	0.3 (3)
C4—C3—C8—C7	108.78 (15)	O5—C9—C23—C24	−71.60 (17)
C2—C3—C8—C7	−0.01 (15)	C10—C9—C23—C24	164.95 (13)
C4—C3—C8—C9	0.87 (19)	C8—C9—C23—C24	54.67 (18)
C2—C3—C8—C9	−107.93 (15)	C25—N2—C24—O6	3.3 (2)
C7—C8—C9—O5	−176.46 (13)	C25—N2—C24—C23	−176.58 (14)
C3—C8—C9—O5	−68.37 (18)	C9—C23—C24—O6	−136.58 (16)
C7—C8—C9—C10	−52.31 (15)	C9—C23—C24—N2	43.3 (2)
C3—C8—C9—C10	55.78 (16)	C24—N2—C25—C26	−73.50 (18)
C7—C8—C9—C23	64.93 (16)	C24—N2—C25—C27	165.92 (14)
C3—C8—C9—C23	173.02 (13)	N2—C25—C26—O7	−25.6 (2)
O5—C9—C10—C11	165.98 (13)	C27—C25—C26—O7	96.15 (19)
C23—C9—C10—C11	−77.43 (16)	N2—C25—C26—O8	157.55 (14)
C8—C9—C10—C11	40.54 (14)	C27—C25—C26—O8	−80.72 (17)
O5—C9—C10—C5	68.97 (18)	N2—C25—C27—C28	−51.65 (19)
C23—C9—C10—C5	−174.44 (14)	C26—C25—C27—C28	−173.14 (14)
C8—C9—C10—C5	−56.47 (16)	C25—C27—C28—C29	−68.3 (2)
C4—C5—C10—C9	1.2 (2)	C25—C27—C28—C33	109.20 (18)
C6—C5—C10—C9	105.14 (15)	C33—C28—C29—C30	−0.9 (3)
C4—C5—C10—C11	−103.58 (15)	C27—C28—C29—C30	176.60 (16)
C6—C5—C10—C11	0.32 (13)	C28—C29—C30—C31	1.2 (3)
C1—C7—C11—C10	−127.46 (15)	C29—C30—C31—C32	−0.9 (3)
C8—C7—C11—C10	−17.57 (18)	C30—C31—C32—C33	0.3 (3)
C1—C7—C11—C6	−34.67 (17)	C31—C32—C33—C28	−0.1 (3)
C8—C7—C11—C6	75.21 (16)	C29—C28—C33—C32	0.4 (3)
C9—C10—C11—C7	−14.54 (17)	C27—C28—C33—C32	−177.14 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6i	0.95 (1)	1.90 (1)	2.8399 (18)	172 (2)
N2—H2N···O5	0.96 (1)	2.01 (2)	2.7579 (18)	134 (2)
O1—H1O···O2	0.96 (1)	1.79 (2)	2.6649 (16)	150 (2)
O5—H5O···O1	0.95 (1)	1.58 (1)	2.4886 (16)	158 (3)
O4—H4O···O7ii	0.96 (1)	1.84 (2)	2.7425 (18)	154 (2)
O8—H8O···O5iii	0.97 (1)	1.68 (1)	2.6501 (17)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6i	0.95 (1)	1.90 (1)	2.8399 (18)	172 (2)
N2—H2N⋯O5	0.96 (1)	2.01 (2)	2.7579 (18)	134 (2)
O1—H1O⋯O2	0.96 (1)	1.79 (2)	2.6649 (16)	150 (2)
O5—H5O⋯O1	0.95 (1)	1.58 (1)	2.4886 (16)	158 (3)
O4—H4O⋯O7ii	0.96 (1)	1.84 (2)	2.7425 (18)	154 (2)
O8—H8O⋯O5iii	0.97 (1)	1.68 (1)	2.6501 (17)	177 (3)

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