Dimethyl 2-[22,24-dimethyl-23-oxo-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(29)H(33)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96 (5)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-H⋯O hydrogen bonds.

Related literature

For general background to the design, synthesis, chemical properties and applications of macrocyclic ligands for 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 ▶, 2012 ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶).

Experimental

Crystal data

C29H33NO8

M = 523.56

Triclinic,

a = 8.8135 (4) Å

b = 8.9469 (4) Å

c = 18.3067 (9) Å

α = 79.077 (1)°

β = 78.218 (1)°

γ = 69.800 (1)°

V = 1315.05 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.972, T max = 0.976

17255 measured reflections

7669 independent reflections

6322 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.00

7669 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.26 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/S1600536812018867/cv5289sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018867/cv5289Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018867/cv5289Isup3.cml

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

C29H33NO8	Z = 2
Mr = 523.56	F(000) = 556
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8135 (4) Å	Cell parameters from 7696 reflections
b = 8.9469 (4) Å	θ = 2.3–32.6°
c = 18.3067 (9) Å	µ = 0.10 mm−1
α = 79.077 (1)°	T = 100 K
β = 78.218 (1)°	Prism, yellow
γ = 69.800 (1)°	0.30 × 0.25 × 0.25 mm
V = 1315.05 (11) Å3

Bruker APEXII CCD diffractometer	7669 independent reflections
Radiation source: fine-focus sealed tube	6322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.972, Tmax = 0.976	k = −12→12
17255 measured reflections	l = −25→25

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.545P] where P = (Fo2 + 2Fc2)/3
7669 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.26 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	1.13161 (11)	−0.16633 (12)	0.31814 (5)	0.0276 (2)
O2	0.92344 (12)	−0.11393 (13)	0.41308 (5)	0.0310 (2)
O3	1.00781 (15)	0.19034 (13)	0.35751 (6)	0.0359 (3)
O4	0.85150 (11)	0.41619 (10)	0.29707 (5)	0.01918 (17)
O5	0.47470 (11)	0.60218 (10)	0.08211 (5)	0.02019 (18)
C1	0.81920 (13)	0.31443 (12)	0.14927 (6)	0.01163 (19)
H1	0.8403	0.4119	0.1582	0.014*
C2	0.98327 (13)	0.19396 (13)	0.12362 (6)	0.01201 (19)
C3	1.12344 (13)	0.23975 (13)	0.10998 (6)	0.0146 (2)
H3	1.1152	0.3423	0.1208	0.018*
C4	1.27594 (14)	0.13916 (14)	0.08085 (7)	0.0172 (2)
H4	1.3694	0.1739	0.0709	0.021*
C5	1.28898 (14)	−0.01176 (14)	0.06661 (6)	0.0168 (2)
H5	1.3922	−0.0814	0.0472	0.020*
C6	1.15144 (13)	−0.06216 (13)	0.08057 (6)	0.0153 (2)
H6	1.1615	−0.1663	0.0713	0.018*
C7	0.99921 (13)	0.04013 (13)	0.10818 (6)	0.01280 (19)
O8	0.85858 (9)	0.00052 (9)	0.12206 (5)	0.01476 (16)
C9	0.86878 (14)	−0.15809 (13)	0.11310 (7)	0.0161 (2)
H9A	0.9469	−0.2391	0.1441	0.019*
H9B	0.9060	−0.1764	0.0598	0.019*
C10	0.69933 (14)	−0.16997 (14)	0.13859 (7)	0.0176 (2)
H10A	0.6193	−0.0781	0.1131	0.021*
H10B	0.6944	−0.2704	0.1254	0.021*
O11	0.66061 (10)	−0.16906 (10)	0.21772 (5)	0.01780 (17)
C12	0.48952 (14)	−0.13173 (14)	0.24487 (7)	0.0183 (2)
H12A	0.4585	−0.2308	0.2550	0.022*
H12B	0.4261	−0.0563	0.2066	0.022*
C13	0.45236 (15)	−0.05669 (14)	0.31593 (7)	0.0190 (2)
H13A	0.3363	−0.0381	0.3384	0.023*
H13B	0.5221	−0.1275	0.3531	0.023*
O14	0.48591 (11)	0.09270 (10)	0.29488 (5)	0.01821 (17)
C15	0.46024 (14)	0.18691 (14)	0.34945 (6)	0.0164 (2)
C16	0.39367 (15)	0.15084 (15)	0.42393 (7)	0.0212 (2)
H16	0.3667	0.0544	0.4394	0.025*
C17	0.36684 (16)	0.25667 (17)	0.47570 (7)	0.0240 (3)
H17	0.3216	0.2319	0.5264	0.029*
C18	0.40564 (16)	0.39754 (16)	0.45368 (7)	0.0233 (3)
H18	0.3852	0.4706	0.4888	0.028*
C19	0.47515 (15)	0.43101 (15)	0.37938 (7)	0.0191 (2)
H19	0.5033	0.5269	0.3646	0.023*
C20	0.50442 (13)	0.32768 (13)	0.32630 (6)	0.0153 (2)
C21	0.57630 (13)	0.37356 (13)	0.24585 (6)	0.01339 (19)
H21	0.5980	0.4769	0.2439	0.016*
C22	0.45975 (13)	0.40020 (13)	0.18780 (6)	0.0150 (2)
H22	0.4553	0.2934	0.1812	0.018*
C23	0.53992 (13)	0.47026 (13)	0.11450 (6)	0.0138 (2)
C24	0.71063 (13)	0.36643 (13)	0.08583 (6)	0.01280 (19)
H24	0.7019	0.2674	0.0717	0.015*
N25	0.73307 (11)	0.25314 (11)	0.22023 (5)	0.01215 (17)
C26	0.83687 (13)	0.17022 (13)	0.27554 (6)	0.01333 (19)
C27	0.87169 (13)	0.01127 (13)	0.29155 (6)	0.0148 (2)
H27	0.8154	−0.0378	0.2695	0.018*
C28	0.99175 (14)	−0.09596 (14)	0.34131 (6)	0.0165 (2)
C29	1.0350 (2)	−0.2151 (2)	0.46417 (8)	0.0398 (4)
H29A	0.9748	−0.2231	0.5153	0.060*
H29B	1.1207	−0.1680	0.4634	0.060*
H29C	1.0849	−0.3224	0.4484	0.060*
C30	0.90969 (15)	0.25603 (14)	0.31496 (6)	0.0180 (2)
C31	0.89526 (17)	0.51070 (16)	0.34025 (7)	0.0243 (3)
H31A	0.8661	0.6228	0.3167	0.036*
H31B	1.0132	0.4685	0.3416	0.036*
H31C	0.8361	0.5049	0.3917	0.036*
C32	0.28641 (15)	0.50733 (16)	0.21208 (7)	0.0231 (2)
H32A	0.2222	0.5306	0.1711	0.035*
H32B	0.2901	0.6080	0.2242	0.035*
H32C	0.2355	0.4522	0.2566	0.035*
C33	0.78760 (14)	0.45247 (14)	0.01605 (6)	0.0161 (2)
H33A	0.7183	0.4816	−0.0234	0.024*
H33B	0.8962	0.3813	−0.0020	0.024*
H33C	0.7979	0.5499	0.0286	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0192 (4)	0.0318 (5)	0.0246 (5)	0.0014 (4)	−0.0035 (3)	−0.0044 (4)
O2	0.0206 (5)	0.0405 (6)	0.0195 (4)	−0.0025 (4)	−0.0026 (3)	0.0111 (4)
O3	0.0498 (7)	0.0263 (5)	0.0397 (6)	−0.0101 (5)	−0.0305 (5)	−0.0021 (4)
O4	0.0235 (4)	0.0171 (4)	0.0210 (4)	−0.0094 (3)	−0.0050 (3)	−0.0045 (3)
O5	0.0182 (4)	0.0139 (4)	0.0251 (4)	−0.0013 (3)	−0.0047 (3)	−0.0001 (3)
C1	0.0116 (4)	0.0106 (4)	0.0123 (4)	−0.0034 (4)	−0.0010 (3)	−0.0018 (3)
C2	0.0114 (4)	0.0120 (5)	0.0117 (4)	−0.0028 (4)	−0.0017 (3)	−0.0011 (3)
C3	0.0144 (5)	0.0140 (5)	0.0162 (5)	−0.0058 (4)	−0.0024 (4)	−0.0010 (4)
C4	0.0123 (5)	0.0181 (5)	0.0206 (5)	−0.0052 (4)	−0.0018 (4)	−0.0011 (4)
C5	0.0115 (5)	0.0176 (5)	0.0186 (5)	−0.0020 (4)	−0.0012 (4)	−0.0024 (4)
C6	0.0144 (5)	0.0126 (5)	0.0170 (5)	−0.0023 (4)	−0.0013 (4)	−0.0030 (4)
C7	0.0121 (5)	0.0128 (5)	0.0134 (5)	−0.0042 (4)	−0.0016 (4)	−0.0015 (4)
O8	0.0120 (4)	0.0109 (3)	0.0219 (4)	−0.0044 (3)	0.0003 (3)	−0.0052 (3)
C9	0.0161 (5)	0.0115 (5)	0.0220 (5)	−0.0048 (4)	−0.0016 (4)	−0.0052 (4)
C10	0.0185 (5)	0.0163 (5)	0.0212 (5)	−0.0084 (4)	−0.0015 (4)	−0.0061 (4)
O11	0.0150 (4)	0.0192 (4)	0.0191 (4)	−0.0060 (3)	−0.0012 (3)	−0.0026 (3)
C12	0.0155 (5)	0.0170 (5)	0.0239 (6)	−0.0081 (4)	0.0001 (4)	−0.0041 (4)
C13	0.0216 (6)	0.0161 (5)	0.0205 (5)	−0.0107 (4)	0.0010 (4)	−0.0012 (4)
O14	0.0242 (4)	0.0152 (4)	0.0174 (4)	−0.0111 (3)	0.0023 (3)	−0.0039 (3)
C15	0.0148 (5)	0.0171 (5)	0.0174 (5)	−0.0053 (4)	−0.0001 (4)	−0.0042 (4)
C16	0.0224 (6)	0.0226 (6)	0.0186 (5)	−0.0107 (5)	0.0021 (4)	−0.0019 (4)
C17	0.0237 (6)	0.0315 (7)	0.0160 (5)	−0.0106 (5)	0.0031 (4)	−0.0045 (5)
C18	0.0239 (6)	0.0285 (6)	0.0190 (6)	−0.0101 (5)	0.0036 (4)	−0.0108 (5)
C19	0.0186 (5)	0.0194 (5)	0.0201 (5)	−0.0072 (4)	0.0016 (4)	−0.0069 (4)
C20	0.0135 (5)	0.0165 (5)	0.0154 (5)	−0.0047 (4)	0.0005 (4)	−0.0037 (4)
C21	0.0125 (5)	0.0121 (5)	0.0151 (5)	−0.0040 (4)	0.0007 (4)	−0.0036 (4)
C22	0.0118 (5)	0.0151 (5)	0.0177 (5)	−0.0041 (4)	−0.0009 (4)	−0.0029 (4)
C23	0.0131 (5)	0.0128 (5)	0.0171 (5)	−0.0042 (4)	−0.0038 (4)	−0.0039 (4)
C24	0.0132 (5)	0.0115 (4)	0.0132 (5)	−0.0027 (4)	−0.0026 (4)	−0.0020 (3)
N25	0.0113 (4)	0.0119 (4)	0.0116 (4)	−0.0025 (3)	−0.0006 (3)	−0.0013 (3)
C26	0.0128 (5)	0.0155 (5)	0.0116 (4)	−0.0047 (4)	−0.0007 (4)	−0.0023 (4)
C27	0.0135 (5)	0.0160 (5)	0.0143 (5)	−0.0046 (4)	−0.0013 (4)	−0.0015 (4)
C28	0.0177 (5)	0.0153 (5)	0.0175 (5)	−0.0065 (4)	−0.0040 (4)	−0.0007 (4)
C29	0.0299 (7)	0.0530 (10)	0.0234 (7)	−0.0045 (7)	−0.0089 (6)	0.0145 (6)
C30	0.0213 (5)	0.0184 (5)	0.0161 (5)	−0.0074 (4)	−0.0036 (4)	−0.0033 (4)
C31	0.0294 (6)	0.0251 (6)	0.0251 (6)	−0.0148 (5)	−0.0011 (5)	−0.0111 (5)
C32	0.0130 (5)	0.0273 (6)	0.0247 (6)	−0.0018 (4)	−0.0006 (4)	−0.0046 (5)
C33	0.0164 (5)	0.0156 (5)	0.0143 (5)	−0.0037 (4)	−0.0020 (4)	−0.0005 (4)

O1—C28	1.2031 (15)	C15—C16	1.3947 (16)
O2—C28	1.3335 (14)	C15—C20	1.4094 (16)
O2—C29	1.4495 (16)	C16—C17	1.3944 (18)
O3—C30	1.2045 (15)	C16—H16	0.9500
O4—C30	1.3442 (14)	C17—C18	1.3845 (19)
O4—C31	1.4461 (14)	C17—H17	0.9500
O5—C23	1.2167 (14)	C18—C19	1.3954 (17)
C1—N25	1.4761 (13)	C18—H18	0.9500
C1—C2	1.5203 (14)	C19—C20	1.3924 (16)
C1—C24	1.5564 (14)	C19—H19	0.9500
C1—H1	1.0000	C20—C21	1.5194 (15)
C2—C3	1.3932 (15)	C21—N25	1.4794 (13)
C2—C7	1.4113 (15)	C21—C22	1.5563 (15)
C3—C4	1.3981 (15)	C21—H21	1.0000
C3—H3	0.9500	C22—C23	1.5142 (15)
C4—C5	1.3851 (16)	C22—C32	1.5242 (16)
C4—H4	0.9500	C22—H22	1.0000
C5—C6	1.3948 (16)	C23—C24	1.5163 (15)
C5—H5	0.9500	C24—C33	1.5227 (15)
C6—C7	1.3940 (15)	C24—H24	1.0000
C6—H6	0.9500	N25—C26	1.4274 (13)
C7—O8	1.3664 (13)	C26—C27	1.3341 (15)
O8—C9	1.4292 (13)	C26—C30	1.5037 (16)
C9—C10	1.5052 (16)	C27—C28	1.4937 (15)
C9—H9A	0.9900	C27—H27	0.9500
C9—H9B	0.9900	C29—H29A	0.9800
C10—O11	1.4198 (14)	C29—H29B	0.9800
C10—H10A	0.9900	C29—H29C	0.9800
C10—H10B	0.9900	C31—H31A	0.9800
O11—C12	1.4288 (14)	C31—H31B	0.9800
C12—C13	1.5017 (17)	C31—H31C	0.9800
C12—H12A	0.9900	C32—H32A	0.9800
C12—H12B	0.9900	C32—H32B	0.9800
C13—O14	1.4331 (13)	C32—H32C	0.9800
C13—H13A	0.9900	C33—H33A	0.9800
C13—H13B	0.9900	C33—H33B	0.9800
O14—C15	1.3619 (14)	C33—H33C	0.9800
C28—O2—C29	114.81 (10)	C20—C19—H19	119.1
C30—O4—C31	115.93 (10)	C18—C19—H19	119.1
N25—C1—C2	112.76 (8)	C19—C20—C15	118.01 (10)
N25—C1—C24	110.82 (8)	C19—C20—C21	119.09 (10)
C2—C1—C24	109.93 (8)	C15—C20—C21	122.86 (10)
N25—C1—H1	107.7	N25—C21—C20	112.83 (9)
C2—C1—H1	107.7	N25—C21—C22	107.37 (8)
C24—C1—H1	107.7	C20—C21—C22	113.45 (9)
C3—C2—C7	117.97 (10)	N25—C21—H21	107.6
C3—C2—C1	119.08 (9)	C20—C21—H21	107.6
C7—C2—C1	122.83 (9)	C22—C21—H21	107.6
C2—C3—C4	121.90 (10)	C23—C22—C32	112.42 (9)
C2—C3—H3	119.0	C23—C22—C21	105.42 (9)
C4—C3—H3	119.0	C32—C22—C21	112.95 (9)
C5—C4—C3	119.14 (10)	C23—C22—H22	108.6
C5—C4—H4	120.4	C32—C22—H22	108.6
C3—C4—H4	120.4	C21—C22—H22	108.6
C4—C5—C6	120.41 (10)	O5—C23—C22	122.66 (10)
C4—C5—H5	119.8	O5—C23—C24	122.31 (10)
C6—C5—H5	119.8	C22—C23—C24	114.99 (9)
C7—C6—C5	120.08 (10)	C23—C24—C33	111.37 (9)
C7—C6—H6	120.0	C23—C24—C1	110.07 (9)
C5—C6—H6	120.0	C33—C24—C1	111.12 (9)
O8—C7—C6	123.53 (10)	C23—C24—H24	108.0
O8—C7—C2	115.99 (9)	C33—C24—H24	108.0
C6—C7—C2	120.48 (10)	C1—C24—H24	108.0
C7—O8—C9	118.60 (8)	C26—N25—C1	113.70 (8)
O8—C9—C10	106.33 (9)	C26—N25—C21	116.78 (8)
O8—C9—H9A	110.5	C1—N25—C21	112.17 (8)
C10—C9—H9A	110.5	C27—C26—N25	118.50 (10)
O8—C9—H9B	110.5	C27—C26—C30	119.42 (10)
C10—C9—H9B	110.5	N25—C26—C30	122.07 (10)
H9A—C9—H9B	108.7	C26—C27—C28	125.47 (10)
O11—C10—C9	108.85 (9)	C26—C27—H27	117.3
O11—C10—H10A	109.9	C28—C27—H27	117.3
C9—C10—H10A	109.9	O1—C28—O2	123.98 (11)
O11—C10—H10B	109.9	O1—C28—C27	123.42 (11)
C9—C10—H10B	109.9	O2—C28—C27	112.43 (10)
H10A—C10—H10B	108.3	O2—C29—H29A	109.5
C10—O11—C12	113.40 (9)	O2—C29—H29B	109.5
O11—C12—C13	108.73 (9)	H29A—C29—H29B	109.5
O11—C12—H12A	109.9	O2—C29—H29C	109.5
C13—C12—H12A	109.9	H29A—C29—H29C	109.5
O11—C12—H12B	109.9	H29B—C29—H29C	109.5
C13—C12—H12B	109.9	O3—C30—O4	123.78 (11)
H12A—C12—H12B	108.3	O3—C30—C26	124.56 (11)
O14—C13—C12	106.22 (9)	O4—C30—C26	111.67 (10)
O14—C13—H13A	110.5	O4—C31—H31A	109.5
C12—C13—H13A	110.5	O4—C31—H31B	109.5
O14—C13—H13B	110.5	H31A—C31—H31B	109.5
C12—C13—H13B	110.5	O4—C31—H31C	109.5
H13A—C13—H13B	108.7	H31A—C31—H31C	109.5
C15—O14—C13	118.32 (9)	H31B—C31—H31C	109.5
O14—C15—C16	123.61 (10)	C22—C32—H32A	109.5
O14—C15—C20	115.78 (10)	C22—C32—H32B	109.5
C16—C15—C20	120.60 (11)	H32A—C32—H32B	109.5
C17—C16—C15	119.83 (11)	C22—C32—H32C	109.5
C17—C16—H16	120.1	H32A—C32—H32C	109.5
C15—C16—H16	120.1	H32B—C32—H32C	109.5
C18—C17—C16	120.47 (11)	C24—C33—H33A	109.5
C18—C17—H17	119.8	C24—C33—H33B	109.5
C16—C17—H17	119.8	H33A—C33—H33B	109.5
C17—C18—C19	119.25 (11)	C24—C33—H33C	109.5
C17—C18—H18	120.4	H33A—C33—H33C	109.5
C19—C18—H18	120.4	H33B—C33—H33C	109.5
C20—C19—C18	121.80 (11)
N25—C1—C2—C3	−124.90 (10)	N25—C21—C22—C23	−63.60 (10)
C24—C1—C2—C3	110.89 (11)	C20—C21—C22—C23	171.03 (9)
N25—C1—C2—C7	59.33 (13)	N25—C21—C22—C32	173.28 (9)
C24—C1—C2—C7	−64.88 (12)	C20—C21—C22—C32	47.91 (13)
C7—C2—C3—C4	0.94 (16)	C32—C22—C23—O5	4.30 (15)
C1—C2—C3—C4	−175.04 (10)	C21—C22—C23—O5	−119.16 (11)
C2—C3—C4—C5	−1.41 (17)	C32—C22—C23—C24	−177.93 (9)
C3—C4—C5—C6	0.54 (17)	C21—C22—C23—C24	58.60 (11)
C4—C5—C6—C7	0.76 (17)	O5—C23—C24—C33	2.98 (15)
C5—C6—C7—O8	178.88 (10)	C22—C23—C24—C33	−174.79 (9)
C5—C6—C7—C2	−1.24 (16)	O5—C23—C24—C1	126.69 (11)
C3—C2—C7—O8	−179.72 (9)	C22—C23—C24—C1	−51.08 (12)
C1—C2—C7—O8	−3.90 (15)	N25—C1—C24—C23	47.70 (11)
C3—C2—C7—C6	0.40 (15)	C2—C1—C24—C23	173.02 (8)
C1—C2—C7—C6	176.21 (10)	N25—C1—C24—C33	171.55 (8)
C6—C7—O8—C9	4.66 (15)	C2—C1—C24—C33	−63.13 (11)
C2—C7—O8—C9	−175.22 (9)	C2—C1—N25—C26	42.83 (12)
C7—O8—C9—C10	175.16 (9)	C24—C1—N25—C26	166.55 (9)
O8—C9—C10—O11	−69.40 (11)	C2—C1—N25—C21	178.07 (8)
C9—C10—O11—C12	162.34 (9)	C24—C1—N25—C21	−58.22 (11)
C10—O11—C12—C13	−152.82 (9)	C20—C21—N25—C26	−33.60 (13)
O11—C12—C13—O14	65.01 (12)	C22—C21—N25—C26	−159.34 (9)
C12—C13—O14—C15	179.28 (9)	C20—C21—N25—C1	−167.36 (9)
C13—O14—C15—C16	−4.05 (17)	C22—C21—N25—C1	66.89 (10)
C13—O14—C15—C20	176.40 (10)	C1—N25—C26—C27	−109.15 (11)
O14—C15—C16—C17	−178.01 (11)	C21—N25—C26—C27	117.77 (11)
C20—C15—C16—C17	1.53 (18)	C1—N25—C26—C30	69.80 (13)
C15—C16—C17—C18	0.1 (2)	C21—N25—C26—C30	−63.28 (13)
C16—C17—C18—C19	−1.3 (2)	N25—C26—C27—C28	172.93 (10)
C17—C18—C19—C20	0.99 (19)	C30—C26—C27—C28	−6.05 (17)
C18—C19—C20—C15	0.57 (18)	C29—O2—C28—O1	5.6 (2)
C18—C19—C20—C21	178.40 (11)	C29—O2—C28—C27	−179.12 (12)
O14—C15—C20—C19	177.74 (10)	C26—C27—C28—O1	−94.78 (16)
C16—C15—C20—C19	−1.83 (17)	C26—C27—C28—O2	89.87 (14)
O14—C15—C20—C21	0.00 (16)	C31—O4—C30—O3	−8.58 (18)
C16—C15—C20—C21	−179.57 (11)	C31—O4—C30—C26	171.27 (9)
C19—C20—C21—N25	121.39 (11)	C27—C26—C30—O3	5.07 (19)
C15—C20—C21—N25	−60.89 (14)	N25—C26—C30—O3	−173.87 (12)
C19—C20—C21—C22	−116.21 (12)	C27—C26—C30—O4	−174.78 (10)
C15—C20—C21—C22	61.51 (14)	N25—C26—C30—O4	6.28 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.99	2.56	3.2877 (18)	130
C29—H29A···O3ii	0.98	2.44	3.2498 (18)	139
C33—H33A···O5iii	0.98	2.56	3.4092 (16)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.99	2.56	3.2877 (18)	130
C29—H29A⋯O3ii	0.98	2.44	3.2498 (18)	139
C33—H33A⋯O5iii	0.98	2.56	3.4092 (16)	145

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