Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

The title compound, C(39)H(37)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.61 (5)° between the two carboxyl-ate groups. The crystal packing is stabilized by the weak C-H⋯O hydrogen bonds.

Related literature

For general background to the design, synthesis, chemical properties and applications of macrocyclic ligands in coordination chemistry, see: Hiraoka (1978 ▶); Pedersen (1988 ▶); Schwan & Warkentin (1988 ▶); Gokel & Murillo (1996 ▶); Bradshaw & Izatt (1997 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Anh et al. (2008 ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶).

Experimental

Crystal data

C39H37NO8

M = 647.70

Triclinic,

a = 10.9914 (6) Å

b = 11.7868 (6) Å

c = 13.7725 (7) Å

α = 114.306 (1)°

β = 91.211 (1)°

γ = 91.984 (1)°

V = 1623.91 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.975, T max = 0.982

19532 measured reflections

8601 independent reflections

7062 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.00

8601 reflections

435 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015206/cv5280sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015206/cv5280Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015206/cv5280Isup3.cml

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

C39H37NO8	Z = 2
Mr = 647.70	F(000) = 684
Triclinic, P1	Dx = 1.325 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9914 (6) Å	Cell parameters from 8458 reflections
b = 11.7868 (6) Å	θ = 2.4–32.6°
c = 13.7725 (7) Å	µ = 0.09 mm−1
α = 114.306 (1)°	T = 100 K
β = 91.211 (1)°	Prism, colourless
γ = 91.984 (1)°	0.28 × 0.22 × 0.20 mm
V = 1623.91 (15) Å3

Bruker APEXII CCD diffractometer	8601 independent reflections
Radiation source: fine-focus sealed tube	7062 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 29.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.975, Tmax = 0.982	k = −16→16
19532 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.049P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
8601 reflections	(Δ/σ)max = 0.001
435 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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	0.81524 (10)	1.05479 (9)	0.57180 (7)	0.0297 (2)
O2	0.75693 (9)	0.74987 (9)	−0.10597 (7)	0.0250 (2)
O3	0.72502 (8)	0.57344 (8)	−0.08306 (7)	0.01937 (18)
O4	0.51599 (9)	0.71161 (10)	0.19678 (7)	0.0273 (2)
O5	0.52850 (8)	0.70160 (8)	0.03110 (7)	0.01941 (18)
C1	0.77006 (10)	0.78011 (10)	0.32029 (9)	0.0143 (2)
H1	0.6900	0.7604	0.3444	0.017*
C2	0.83008 (11)	0.65818 (11)	0.26061 (9)	0.0155 (2)
C3	0.77594 (11)	0.54883 (11)	0.25838 (10)	0.0189 (2)
H3	0.7002	0.5521	0.2912	0.023*
C4	0.82952 (12)	0.43446 (12)	0.20946 (11)	0.0239 (3)
H4	0.7917	0.3611	0.2102	0.029*
C5	0.93852 (13)	0.42927 (12)	0.15987 (11)	0.0268 (3)
H5	0.9751	0.3515	0.1253	0.032*
C6	0.99528 (12)	0.53692 (12)	0.16008 (11)	0.0229 (3)
H6	1.0698	0.5324	0.1252	0.028*
C7	0.94239 (11)	0.65107 (11)	0.21156 (9)	0.0174 (2)
O8	0.99408 (8)	0.76150 (8)	0.21894 (7)	0.01886 (18)
C9	1.10551 (11)	0.76050 (12)	0.16679 (11)	0.0224 (3)
H9A	1.0964	0.7037	0.0902	0.027*
H9B	1.1721	0.7320	0.1995	0.027*
C10	1.13320 (11)	0.89193 (12)	0.18009 (10)	0.0221 (3)
H10A	1.1332	0.9495	0.2565	0.027*
H10B	1.2147	0.8986	0.1532	0.027*
O11	1.04269 (8)	0.92460 (8)	0.12188 (7)	0.01924 (18)
C12	1.02925 (12)	1.05545 (12)	0.16091 (11)	0.0231 (3)
H12A	1.0920	1.0931	0.1312	0.028*
H12B	1.0400	1.0943	0.2396	0.028*
C13	0.90450 (12)	1.07848 (12)	0.12842 (11)	0.0232 (3)
H13A	0.8981	1.1676	0.1429	0.028*
H13B	0.8875	1.0279	0.0514	0.028*
O14	0.82056 (8)	1.04353 (8)	0.19004 (7)	0.01873 (18)
C15	0.69884 (11)	1.05639 (11)	0.17862 (9)	0.0171 (2)
C16	0.64916 (13)	1.10929 (11)	0.11422 (10)	0.0219 (3)
H16	0.7004	1.1358	0.0721	0.026*
C17	0.52405 (13)	1.12324 (12)	0.11168 (11)	0.0251 (3)
H17	0.4903	1.1604	0.0683	0.030*
C18	0.44833 (12)	1.08351 (12)	0.17164 (11)	0.0237 (3)
H18	0.3631	1.0939	0.1702	0.028*
C19	0.49853 (11)	1.02807 (11)	0.23404 (10)	0.0194 (2)
H19	0.4464	0.9996	0.2743	0.023*
C20	0.62324 (11)	1.01343 (10)	0.23881 (9)	0.0155 (2)
C21	0.67458 (10)	0.95795 (10)	0.31156 (9)	0.0142 (2)
H21	0.6051	0.9316	0.3445	0.017*
C22	0.75899 (11)	1.05411 (10)	0.40273 (9)	0.0148 (2)
H22	0.8318	1.0718	0.3680	0.018*
C23	0.80526 (11)	0.99655 (11)	0.47590 (9)	0.0173 (2)
C24	0.84906 (10)	0.86418 (11)	0.42172 (9)	0.0152 (2)
H24	0.9333	0.8709	0.3979	0.018*
N25	0.74589 (9)	0.84833 (9)	0.25395 (7)	0.01416 (19)
C26	0.69852 (10)	1.17631 (10)	0.45793 (9)	0.0154 (2)
C27	0.72415 (11)	1.27232 (11)	0.42612 (9)	0.0181 (2)
H27	0.7821	1.2609	0.3730	0.022*
C28	0.66661 (12)	1.38434 (12)	0.47051 (10)	0.0222 (3)
H28	0.6854	1.4489	0.4480	0.027*
C29	0.58174 (12)	1.40171 (12)	0.54767 (10)	0.0228 (3)
H29	0.5423	1.4783	0.5786	0.027*
C30	0.55464 (11)	1.30695 (12)	0.57959 (10)	0.0217 (3)
H30	0.4960	1.3186	0.6322	0.026*
C31	0.61253 (11)	1.19494 (12)	0.53530 (9)	0.0191 (2)
H31	0.5933	1.1306	0.5579	0.023*
C32	0.85723 (11)	0.79886 (11)	0.49579 (9)	0.0162 (2)
C33	0.75722 (12)	0.79095 (12)	0.55415 (10)	0.0202 (2)
H33	0.6861	0.8338	0.5526	0.024*
C34	0.76049 (13)	0.72117 (13)	0.61443 (10)	0.0257 (3)
H34	0.6922	0.7170	0.6541	0.031*
C35	0.86378 (14)	0.65763 (13)	0.61657 (11)	0.0276 (3)
H35	0.8661	0.6094	0.6573	0.033*
C36	0.96326 (13)	0.66473 (12)	0.55933 (11)	0.0255 (3)
H36	1.0339	0.6211	0.5607	0.031*
C37	0.96060 (11)	0.73542 (11)	0.49962 (10)	0.0196 (2)
H37	1.0298	0.7405	0.4612	0.023*
C38	0.70379 (10)	0.77556 (10)	0.14631 (9)	0.0145 (2)
C39	0.77988 (11)	0.75955 (10)	0.06806 (9)	0.0156 (2)
H39	0.8610	0.7924	0.0891	0.019*
C40	0.75136 (10)	0.69577 (11)	−0.04851 (9)	0.0163 (2)
C41	0.68623 (13)	0.51164 (13)	−0.19471 (10)	0.0246 (3)
H41A	0.6577	0.4258	−0.2111	0.037*
H41B	0.7549	0.5110	−0.2391	0.037*
H41C	0.6198	0.5565	−0.2093	0.037*
C42	0.57397 (11)	0.72587 (11)	0.12884 (9)	0.0166 (2)
C43	0.40551 (12)	0.64856 (14)	0.00728 (11)	0.0258 (3)
H43A	0.3821	0.6318	−0.0666	0.039*
H43B	0.3501	0.7073	0.0556	0.039*
H43C	0.4008	0.5705	0.0167	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0505 (6)	0.0199 (5)	0.0154 (4)	0.0054 (4)	−0.0083 (4)	0.0039 (4)
O2	0.0340 (5)	0.0243 (5)	0.0195 (4)	−0.0045 (4)	−0.0008 (4)	0.0124 (4)
O3	0.0254 (4)	0.0162 (4)	0.0143 (4)	−0.0019 (3)	−0.0010 (3)	0.0044 (3)
O4	0.0246 (5)	0.0382 (6)	0.0198 (4)	−0.0119 (4)	−0.0015 (4)	0.0140 (4)
O5	0.0159 (4)	0.0261 (5)	0.0174 (4)	−0.0025 (3)	−0.0027 (3)	0.0104 (4)
C1	0.0160 (5)	0.0134 (5)	0.0144 (5)	−0.0004 (4)	−0.0005 (4)	0.0069 (4)
C2	0.0175 (5)	0.0148 (5)	0.0139 (5)	0.0007 (4)	−0.0022 (4)	0.0058 (4)
C3	0.0205 (6)	0.0168 (5)	0.0194 (6)	−0.0011 (4)	−0.0018 (4)	0.0076 (5)
C4	0.0284 (7)	0.0145 (6)	0.0289 (7)	−0.0006 (5)	−0.0023 (5)	0.0092 (5)
C5	0.0314 (7)	0.0162 (6)	0.0309 (7)	0.0065 (5)	0.0028 (6)	0.0075 (5)
C6	0.0223 (6)	0.0214 (6)	0.0254 (6)	0.0051 (5)	0.0040 (5)	0.0095 (5)
C7	0.0193 (6)	0.0156 (5)	0.0181 (5)	0.0001 (4)	−0.0012 (4)	0.0078 (4)
O8	0.0176 (4)	0.0174 (4)	0.0226 (4)	0.0005 (3)	0.0043 (3)	0.0091 (3)
C9	0.0177 (6)	0.0265 (6)	0.0262 (6)	0.0031 (5)	0.0054 (5)	0.0137 (5)
C10	0.0178 (6)	0.0275 (7)	0.0227 (6)	−0.0040 (5)	−0.0008 (5)	0.0125 (5)
O11	0.0222 (4)	0.0162 (4)	0.0182 (4)	−0.0015 (3)	−0.0001 (3)	0.0062 (3)
C12	0.0260 (6)	0.0158 (6)	0.0256 (6)	−0.0035 (5)	0.0063 (5)	0.0065 (5)
C13	0.0295 (7)	0.0194 (6)	0.0257 (6)	0.0016 (5)	0.0093 (5)	0.0139 (5)
O14	0.0206 (4)	0.0205 (4)	0.0181 (4)	−0.0010 (3)	0.0021 (3)	0.0110 (3)
C15	0.0226 (6)	0.0121 (5)	0.0148 (5)	0.0008 (4)	−0.0011 (4)	0.0039 (4)
C16	0.0322 (7)	0.0166 (6)	0.0181 (6)	0.0000 (5)	−0.0013 (5)	0.0087 (5)
C17	0.0350 (7)	0.0190 (6)	0.0226 (6)	0.0040 (5)	−0.0058 (5)	0.0099 (5)
C18	0.0240 (6)	0.0207 (6)	0.0251 (6)	0.0043 (5)	−0.0051 (5)	0.0082 (5)
C19	0.0221 (6)	0.0162 (5)	0.0183 (6)	0.0013 (4)	−0.0009 (5)	0.0055 (5)
C20	0.0213 (6)	0.0112 (5)	0.0128 (5)	0.0008 (4)	−0.0022 (4)	0.0039 (4)
C21	0.0161 (5)	0.0138 (5)	0.0127 (5)	0.0000 (4)	−0.0004 (4)	0.0056 (4)
C22	0.0174 (5)	0.0136 (5)	0.0131 (5)	−0.0007 (4)	−0.0006 (4)	0.0054 (4)
C23	0.0198 (6)	0.0155 (5)	0.0163 (5)	−0.0018 (4)	−0.0029 (4)	0.0066 (4)
C24	0.0163 (5)	0.0156 (5)	0.0144 (5)	−0.0002 (4)	−0.0009 (4)	0.0071 (4)
N25	0.0176 (5)	0.0122 (4)	0.0120 (4)	0.0008 (3)	−0.0016 (3)	0.0044 (4)
C26	0.0172 (5)	0.0135 (5)	0.0133 (5)	−0.0008 (4)	−0.0025 (4)	0.0037 (4)
C27	0.0210 (6)	0.0168 (5)	0.0161 (5)	−0.0003 (4)	0.0020 (4)	0.0064 (4)
C28	0.0293 (7)	0.0168 (6)	0.0208 (6)	0.0009 (5)	−0.0016 (5)	0.0081 (5)
C29	0.0256 (6)	0.0197 (6)	0.0189 (6)	0.0067 (5)	−0.0014 (5)	0.0035 (5)
C30	0.0182 (6)	0.0260 (6)	0.0168 (6)	0.0011 (5)	0.0010 (4)	0.0047 (5)
C31	0.0217 (6)	0.0195 (6)	0.0159 (5)	−0.0023 (4)	0.0001 (4)	0.0074 (5)
C32	0.0203 (6)	0.0140 (5)	0.0139 (5)	−0.0014 (4)	−0.0030 (4)	0.0055 (4)
C33	0.0219 (6)	0.0195 (6)	0.0179 (6)	0.0000 (5)	0.0005 (5)	0.0064 (5)
C34	0.0335 (7)	0.0241 (6)	0.0193 (6)	−0.0071 (5)	0.0014 (5)	0.0093 (5)
C35	0.0405 (8)	0.0204 (6)	0.0255 (7)	−0.0078 (5)	−0.0087 (6)	0.0143 (5)
C36	0.0290 (7)	0.0181 (6)	0.0294 (7)	−0.0010 (5)	−0.0103 (5)	0.0103 (5)
C37	0.0197 (6)	0.0172 (5)	0.0204 (6)	−0.0003 (4)	−0.0031 (5)	0.0065 (5)
C38	0.0173 (5)	0.0121 (5)	0.0143 (5)	−0.0005 (4)	−0.0020 (4)	0.0060 (4)
C39	0.0170 (5)	0.0135 (5)	0.0164 (5)	−0.0003 (4)	−0.0014 (4)	0.0067 (4)
C40	0.0140 (5)	0.0180 (5)	0.0163 (5)	0.0001 (4)	0.0020 (4)	0.0064 (4)
C41	0.0307 (7)	0.0230 (6)	0.0148 (6)	−0.0048 (5)	−0.0036 (5)	0.0030 (5)
C42	0.0189 (5)	0.0140 (5)	0.0166 (5)	−0.0003 (4)	−0.0009 (4)	0.0061 (4)
C43	0.0185 (6)	0.0328 (7)	0.0259 (7)	−0.0056 (5)	−0.0059 (5)	0.0127 (6)

O1—C23	1.2125 (15)	C19—C20	1.3909 (17)
O2—C40	1.2048 (14)	C19—H19	0.9500
O3—C40	1.3378 (14)	C20—C21	1.5135 (15)
O3—C41	1.4511 (14)	C21—N25	1.4717 (14)
O4—C42	1.2072 (15)	C21—C22	1.5584 (16)
O5—C42	1.3373 (14)	C21—H21	1.0000
O5—C43	1.4422 (15)	C22—C26	1.5101 (16)
C1—N25	1.4703 (14)	C22—C23	1.5164 (16)
C1—C2	1.5141 (16)	C22—H22	1.0000
C1—C24	1.5610 (16)	C23—C24	1.5269 (16)
C1—H1	1.0000	C24—C32	1.5129 (15)
C2—C3	1.3892 (16)	C24—H24	1.0000
C2—C7	1.4081 (17)	N25—C38	1.4297 (14)
C3—C4	1.3935 (17)	C26—C31	1.3934 (16)
C3—H3	0.9500	C26—C27	1.3939 (16)
C4—C5	1.382 (2)	C27—C28	1.3881 (17)
C4—H4	0.9500	C27—H27	0.9500
C5—C6	1.3934 (19)	C28—C29	1.3847 (19)
C5—H5	0.9500	C28—H28	0.9500
C6—C7	1.3918 (17)	C29—C30	1.3844 (19)
C6—H6	0.9500	C29—H29	0.9500
C7—O8	1.3656 (14)	C30—C31	1.3898 (18)
O8—C9	1.4308 (14)	C30—H30	0.9500
C9—C10	1.5025 (18)	C31—H31	0.9500
C9—H9A	0.9900	C32—C37	1.3935 (17)
C9—H9B	0.9900	C32—C33	1.3982 (17)
C10—O11	1.4240 (15)	C33—C34	1.3892 (18)
C10—H10A	0.9900	C33—H33	0.9500
C10—H10B	0.9900	C34—C35	1.388 (2)
O11—C12	1.4234 (15)	C34—H34	0.9500
C12—C13	1.5013 (19)	C35—C36	1.381 (2)
C12—H12A	0.9900	C35—H35	0.9500
C12—H12B	0.9900	C36—C37	1.3914 (18)
C13—O14	1.4268 (14)	C36—H36	0.9500
C13—H13A	0.9900	C37—H37	0.9500
C13—H13B	0.9900	C38—C39	1.3335 (16)
O14—C15	1.3647 (15)	C38—C42	1.4995 (16)
C15—C16	1.3901 (16)	C39—C40	1.4866 (16)
C15—C20	1.4070 (16)	C39—H39	0.9500
C16—C17	1.3921 (19)	C41—H41A	0.9800
C16—H16	0.9500	C41—H41B	0.9800
C17—C18	1.384 (2)	C41—H41C	0.9800
C17—H17	0.9500	C43—H43A	0.9800
C18—C19	1.3919 (17)	C43—H43B	0.9800
C18—H18	0.9500	C43—H43C	0.9800
C40—O3—C41	114.59 (9)	C26—C22—C21	111.27 (9)
C42—O5—C43	115.98 (10)	C23—C22—C21	110.24 (9)
N25—C1—C2	113.05 (9)	C26—C22—H22	106.6
N25—C1—C24	110.14 (9)	C23—C22—H22	106.6
C2—C1—C24	110.35 (9)	C21—C22—H22	106.6
N25—C1—H1	107.7	O1—C23—C22	122.18 (11)
C2—C1—H1	107.7	O1—C23—C24	121.31 (11)
C24—C1—H1	107.7	C22—C23—C24	116.32 (10)
C3—C2—C7	118.04 (11)	C32—C24—C23	113.21 (9)
C3—C2—C1	119.03 (10)	C32—C24—C1	108.91 (9)
C7—C2—C1	122.84 (10)	C23—C24—C1	113.21 (9)
C2—C3—C4	121.92 (12)	C32—C24—H24	107.0
C2—C3—H3	119.0	C23—C24—H24	107.0
C4—C3—H3	119.0	C1—C24—H24	107.0
C5—C4—C3	119.04 (12)	C38—N25—C1	116.67 (9)
C5—C4—H4	120.5	C38—N25—C21	114.50 (9)
C3—C4—H4	120.5	C1—N25—C21	110.81 (9)
C4—C5—C6	120.66 (12)	C31—C26—C27	118.32 (11)
C4—C5—H5	119.7	C31—C26—C22	122.69 (10)
C6—C5—H5	119.7	C27—C26—C22	118.88 (10)
C7—C6—C5	119.73 (12)	C28—C27—C26	121.26 (11)
C7—C6—H6	120.1	C28—C27—H27	119.4
C5—C6—H6	120.1	C26—C27—H27	119.4
O8—C7—C6	123.51 (11)	C29—C28—C27	119.77 (12)
O8—C7—C2	115.92 (10)	C29—C28—H28	120.1
C6—C7—C2	120.57 (11)	C27—C28—H28	120.1
C7—O8—C9	118.88 (9)	C30—C29—C28	119.69 (12)
O8—C9—C10	106.65 (10)	C30—C29—H29	120.2
O8—C9—H9A	110.4	C28—C29—H29	120.2
C10—C9—H9A	110.4	C29—C30—C31	120.50 (12)
O8—C9—H9B	110.4	C29—C30—H30	119.7
C10—C9—H9B	110.4	C31—C30—H30	119.7
H9A—C9—H9B	108.6	C30—C31—C26	120.46 (11)
O11—C10—C9	108.74 (10)	C30—C31—H31	119.8
O11—C10—H10A	109.9	C26—C31—H31	119.8
C9—C10—H10A	109.9	C37—C32—C33	118.52 (11)
O11—C10—H10B	109.9	C37—C32—C24	120.51 (11)
C9—C10—H10B	109.9	C33—C32—C24	120.70 (11)
H10A—C10—H10B	108.3	C34—C33—C32	120.85 (12)
C12—O11—C10	113.17 (10)	C34—C33—H33	119.6
O11—C12—C13	108.94 (10)	C32—C33—H33	119.6
O11—C12—H12A	109.9	C35—C34—C33	119.87 (13)
C13—C12—H12A	109.9	C35—C34—H34	120.1
O11—C12—H12B	109.9	C33—C34—H34	120.1
C13—C12—H12B	109.9	C36—C35—C34	119.87 (12)
H12A—C12—H12B	108.3	C36—C35—H35	120.1
O14—C13—C12	106.48 (10)	C34—C35—H35	120.1
O14—C13—H13A	110.4	C35—C36—C37	120.37 (12)
C12—C13—H13A	110.4	C35—C36—H36	119.8
O14—C13—H13B	110.4	C37—C36—H36	119.8
C12—C13—H13B	110.4	C36—C37—C32	120.52 (12)
H13A—C13—H13B	108.6	C36—C37—H37	119.7
C15—O14—C13	119.73 (10)	C32—C37—H37	119.7
O14—C15—C16	124.16 (11)	C39—C38—N25	118.66 (10)
O14—C15—C20	115.34 (10)	C39—C38—C42	124.16 (10)
C16—C15—C20	120.50 (11)	N25—C38—C42	117.15 (10)
C15—C16—C17	119.74 (12)	C38—C39—C40	126.99 (11)
C15—C16—H16	120.1	C38—C39—H39	116.5
C17—C16—H16	120.1	C40—C39—H39	116.5
C18—C17—C16	120.65 (12)	O2—C40—O3	123.95 (11)
C18—C17—H17	119.7	O2—C40—C39	122.18 (11)
C16—C17—H17	119.7	O3—C40—C39	113.80 (10)
C17—C18—C19	119.21 (12)	O3—C41—H41A	109.5
C17—C18—H18	120.4	O3—C41—H41B	109.5
C19—C18—H18	120.4	H41A—C41—H41B	109.5
C20—C19—C18	121.55 (12)	O3—C41—H41C	109.5
C20—C19—H19	119.2	H41A—C41—H41C	109.5
C18—C19—H19	119.2	H41B—C41—H41C	109.5
C19—C20—C15	118.32 (11)	O4—C42—O5	123.60 (11)
C19—C20—C21	119.78 (11)	O4—C42—C38	123.36 (11)
C15—C20—C21	121.84 (10)	O5—C42—C38	113.02 (10)
N25—C21—C20	112.36 (9)	O5—C43—H43A	109.5
N25—C21—C22	107.51 (9)	O5—C43—H43B	109.5
C20—C21—C22	111.79 (9)	H43A—C43—H43B	109.5
N25—C21—H21	108.4	O5—C43—H43C	109.5
C20—C21—H21	108.4	H43A—C43—H43C	109.5
C22—C21—H21	108.4	H43B—C43—H43C	109.5
C26—C22—C23	115.04 (9)
N25—C1—C2—C3	−125.05 (11)	N25—C1—C24—C32	171.97 (9)
C24—C1—C2—C3	111.10 (12)	C2—C1—C24—C32	−62.52 (12)
N25—C1—C2—C7	58.41 (14)	N25—C1—C24—C23	45.09 (13)
C24—C1—C2—C7	−65.44 (14)	C2—C1—C24—C23	170.60 (9)
C7—C2—C3—C4	−0.05 (18)	C2—C1—N25—C38	39.74 (13)
C1—C2—C3—C4	−176.75 (11)	C24—C1—N25—C38	163.70 (9)
C2—C3—C4—C5	−1.30 (19)	C2—C1—N25—C21	173.16 (9)
C3—C4—C5—C6	1.0 (2)	C24—C1—N25—C21	−62.87 (12)
C4—C5—C6—C7	0.6 (2)	C20—C21—N25—C38	−32.35 (13)
C5—C6—C7—O8	177.52 (12)	C22—C21—N25—C38	−155.76 (9)
C5—C6—C7—C2	−2.00 (19)	C20—C21—N25—C1	−166.85 (9)
C3—C2—C7—O8	−177.85 (10)	C22—C21—N25—C1	69.74 (11)
C1—C2—C7—O8	−1.28 (16)	C23—C22—C26—C31	−46.14 (15)
C3—C2—C7—C6	1.70 (17)	C21—C22—C26—C31	80.13 (13)
C1—C2—C7—C6	178.27 (11)	C23—C22—C26—C27	137.69 (11)
C6—C7—O8—C9	3.25 (17)	C21—C22—C26—C27	−96.03 (12)
C2—C7—O8—C9	−177.21 (10)	C31—C26—C27—C28	0.48 (18)
C7—O8—C9—C10	174.76 (10)	C22—C26—C27—C28	176.81 (11)
O8—C9—C10—O11	−66.55 (13)	C26—C27—C28—C29	−0.20 (19)
C9—C10—O11—C12	156.09 (10)	C27—C28—C29—C30	−0.26 (19)
C10—O11—C12—C13	−156.89 (10)	C28—C29—C30—C31	0.43 (19)
O11—C12—C13—O14	70.43 (12)	C29—C30—C31—C26	−0.14 (19)
C12—C13—O14—C15	178.94 (10)	C27—C26—C31—C30	−0.31 (18)
C13—O14—C15—C16	−4.04 (17)	C22—C26—C31—C30	−176.49 (11)
C13—O14—C15—C20	176.88 (10)	C23—C24—C32—C37	−132.76 (11)
O14—C15—C16—C17	−177.13 (11)	C1—C24—C32—C37	100.36 (12)
C20—C15—C16—C17	1.91 (18)	C23—C24—C32—C33	53.27 (15)
C15—C16—C17—C18	−0.82 (19)	C1—C24—C32—C33	−73.60 (13)
C16—C17—C18—C19	−0.6 (2)	C37—C32—C33—C34	−0.18 (18)
C17—C18—C19—C20	1.01 (19)	C24—C32—C33—C34	173.90 (11)
C18—C19—C20—C15	0.06 (17)	C32—C33—C34—C35	−0.40 (19)
C18—C19—C20—C21	177.24 (11)	C33—C34—C35—C36	0.4 (2)
O14—C15—C20—C19	177.59 (10)	C34—C35—C36—C37	0.1 (2)
C16—C15—C20—C19	−1.53 (17)	C35—C36—C37—C32	−0.70 (19)
O14—C15—C20—C21	0.48 (16)	C33—C32—C37—C36	0.73 (18)
C16—C15—C20—C21	−178.64 (11)	C24—C32—C37—C36	−173.36 (11)
C19—C20—C21—N25	124.26 (11)	C1—N25—C38—C39	−107.40 (12)
C15—C20—C21—N25	−58.67 (14)	C21—N25—C38—C39	120.86 (11)
C19—C20—C21—C22	−114.76 (12)	C1—N25—C38—C42	74.83 (13)
C15—C20—C21—C22	62.31 (14)	C21—N25—C38—C42	−56.91 (13)
N25—C21—C22—C26	173.02 (9)	N25—C38—C39—C40	−175.09 (10)
C20—C21—C22—C26	49.26 (13)	C42—C38—C39—C40	2.52 (19)
N25—C21—C22—C23	−58.10 (11)	C41—O3—C40—O2	−8.29 (17)
C20—C21—C22—C23	178.15 (9)	C41—O3—C40—C39	174.69 (10)
C26—C22—C23—O1	−14.07 (17)	C38—C39—C40—O2	116.68 (14)
C21—C22—C23—O1	−140.87 (12)	C38—C39—C40—O3	−66.24 (15)
C26—C22—C23—C24	170.95 (10)	C43—O5—C42—O4	−3.85 (17)
C21—C22—C23—C24	44.14 (13)	C43—O5—C42—C38	177.49 (10)
O1—C23—C24—C32	22.51 (16)	C39—C38—C42—O4	159.93 (12)
C22—C23—C24—C32	−162.46 (10)	N25—C38—C42—O4	−22.44 (17)
O1—C23—C24—C1	147.08 (12)	C39—C38—C42—O5	−21.41 (16)
C22—C23—C24—C1	−37.89 (14)	N25—C38—C42—O5	156.22 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.58	3.3982 (16)	145
C10—H10A···O1ii	0.99	2.44	3.2433 (16)	138
C12—H12A···O2iii	0.99	2.58	3.5345 (18)	162
C17—H17···O5iv	0.95	2.53	3.4409 (18)	160
C30—H30···O4v	0.95	2.53	3.2834 (16)	136
C41—H41A···O4vi	0.98	2.52	3.3758 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.95	2.58	3.3982 (16)	145
C10—H10A⋯O1ii	0.99	2.44	3.2433 (16)	138
C12—H12A⋯O2iii	0.99	2.58	3.5345 (18)	162
C17—H17⋯O5iv	0.95	2.53	3.4409 (18)	160
C30—H30⋯O4v	0.95	2.53	3.2834 (16)	136
C41—H41A⋯O4vi	0.98	2.52	3.3758 (19)	145

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