Diethyl 2,6-dimethyl-4-[4-(3-phenyl-acrylo-yloxy)phen-yl]-1,4-dihydro-pyridine-3,5-dicarboxyl-ate hemihydrate.

In the title ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydro-pyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, mol-ecules are bridged via O-H⋯O hydrogen bonds involving the partially occupied water mol-ecule, and this arrangement is strengthened by a pair of N-H⋯O hydrogen bonds and C-H⋯O inter-actions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).

Related literature

For the biological activity of ester derivatives, see: Bi et al. (2012 ▶); Bartzatt et al. (2004 ▶); Anadu et al. (2006 ▶).

Experimental

Crystal data

C28H29NO6·0.5H2O

M = 484.53

Monoclinic,

a = 25.4905 (11) Å

b = 8.6166 (4) Å

c = 23.2902 (10) Å

β = 92.235 (2)°

V = 5111.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T min = 0.979, T max = 0.983

24059 measured reflections

5036 independent reflections

3271 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.146

S = 1.09

5036 reflections

344 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004108/su2546sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004108/su2546Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004108/su2546Isup3.cml

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

C28H29NO6·0.5H2O	F(000) = 2056
Mr = 484.53	Dx = 1.259 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8834 reflections
a = 25.4905 (11) Å	θ = 2.1–31.2°
b = 8.6166 (4) Å	µ = 0.09 mm−1
c = 23.2902 (10) Å	T = 293 K
β = 92.235 (2)°	Block, colourless
V = 5111.6 (4) Å3	0.25 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	5036 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −31→21
Tmin = 0.979, Tmax = 0.983	k = −10→10
24059 measured reflections	l = −28→27

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0654P)2 + 1.6916P] where P = (Fo2 + 2Fc2)/3
5036 reflections	(Δ/σ)max = 0.008
344 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O1	0.15295 (6)	0.1181 (2)	0.38244 (6)	0.0831 (6)
O2	0.20401 (5)	0.0099 (2)	0.31780 (6)	0.0765 (6)
O3	0.12749 (6)	0.0181 (2)	0.05234 (7)	0.0902 (7)
O4	0.06211 (5)	−0.14990 (17)	0.04359 (6)	0.0727 (5)
O5	0.03119 (9)	0.5972 (2)	0.17358 (9)	0.1146 (9)
O6	0.10758 (7)	0.50789 (18)	0.14631 (8)	0.0950 (7)
N1	−0.03049 (6)	0.1524 (2)	0.13608 (7)	0.0614 (6)
C1	0.26807 (8)	−0.0271 (3)	0.51329 (8)	0.0651 (7)
C2	0.26107 (10)	0.0205 (4)	0.56879 (10)	0.0966 (10)
C3	0.29518 (13)	−0.0298 (4)	0.61298 (11)	0.1089 (13)
C4	0.33541 (12)	−0.1280 (4)	0.60133 (13)	0.0984 (11)
C5	0.34198 (10)	−0.1753 (3)	0.54686 (13)	0.0945 (11)
C6	0.30910 (8)	−0.1260 (3)	0.50304 (10)	0.0761 (8)
C7	0.23098 (7)	0.0247 (3)	0.46755 (9)	0.0661 (7)
C8	0.23225 (7)	−0.0054 (2)	0.41294 (8)	0.0610 (7)
C9	0.19188 (7)	0.0489 (3)	0.37172 (8)	0.0603 (7)
C10	0.17077 (7)	0.0613 (3)	0.27168 (8)	0.0617 (7)
C11	0.19264 (8)	0.1538 (3)	0.23170 (9)	0.0793 (9)
C12	0.16255 (8)	0.1999 (3)	0.18433 (9)	0.0749 (8)
C13	0.11058 (6)	0.1577 (2)	0.17750 (7)	0.0510 (6)
C14	0.09000 (7)	0.0638 (2)	0.21843 (7)	0.0540 (6)
C15	0.12003 (7)	0.0140 (2)	0.26555 (8)	0.0597 (7)
C16	0.07650 (7)	0.2137 (2)	0.12629 (7)	0.0533 (6)
C17	0.03766 (7)	0.3350 (2)	0.14437 (7)	0.0555 (6)
C18	−0.01294 (8)	0.2973 (2)	0.15185 (8)	0.0583 (7)
C19	−0.00213 (7)	0.0484 (2)	0.10495 (7)	0.0536 (6)
C20	0.04903 (7)	0.0777 (2)	0.09681 (7)	0.0510 (6)
C21	0.08341 (8)	−0.0176 (3)	0.06266 (7)	0.0589 (7)
C22	0.09348 (9)	−0.2500 (3)	0.00904 (10)	0.0840 (9)
C23	0.06010 (12)	−0.3865 (3)	−0.00605 (12)	0.1018 (11)
C24	−0.03430 (8)	−0.0877 (3)	0.08445 (9)	0.0702 (8)
C25	−0.05506 (9)	0.3959 (3)	0.17583 (11)	0.0842 (9)
C26	0.05650 (11)	0.4907 (3)	0.15686 (9)	0.0737 (9)
C27A	0.1365 (2)	0.6471 (6)	0.1590 (2)	0.091 (2)	0.716 (5)
C28A	0.15865 (17)	0.6335 (5)	0.2190 (2)	0.1116 (19)	0.716 (5)
C28B	0.1719 (5)	0.6871 (14)	0.1717 (6)	0.1116 (19)	0.284 (5)
C27B	0.1144 (5)	0.6777 (12)	0.1772 (5)	0.072 (4)	0.284 (5)
O1W	−0.0134 (3)	0.8162 (4)	0.2322 (3)	0.143 (4)	0.500
H3	0.29060	0.00340	0.65040	0.1310*
H4	0.35820	−0.16220	0.63080	0.1180*
H2	0.23350	0.08660	0.57680	0.1160*
H6	0.31440	−0.15950	0.46580	0.0910*
H7	0.20330	0.08640	0.47890	0.0790*
H5	0.36930	−0.24260	0.53910	0.1130*
H11	0.22740	0.18550	0.23630	0.0950*
H12	0.17760	0.26060	0.15640	0.0900*
H14	0.05510	0.03300	0.21440	0.0650*
H15	0.10570	−0.05090	0.29270	0.0720*
H16	0.09960	0.26170	0.09870	0.0640*
H22A	0.12500	−0.28220	0.03050	0.1010*
H8	0.26000	−0.06390	0.39970	0.0730*
H1N	−0.0639 (6)	0.136 (2)	0.1384 (9)	0.0740*
H23B	0.02800	−0.35200	−0.02490	0.1530*
H23C	0.05220	−0.44200	0.02830	0.1530*
H24A	−0.07040	−0.07110	0.09310	0.1050*
H24B	−0.02170	−0.18010	0.10340	0.1050*
H24C	−0.03150	−0.09900	0.04370	0.1050*
H25A	−0.08780	0.34060	0.17370	0.1260*
H25B	−0.05840	0.49020	0.15400	0.1260*
H25C	−0.04600	0.42040	0.21520	0.1260*
H27A	0.11360	0.73670	0.15550	0.1090*	0.716 (5)
H27B	0.16460	0.65930	0.13240	0.1090*	0.716 (5)
H28A	0.13050	0.63070	0.24520	0.1680*	0.716 (5)
H28B	0.18080	0.72120	0.22770	0.1680*	0.716 (5)
H28C	0.17890	0.53980	0.22280	0.1680*	0.716 (5)
H22B	0.10370	−0.19640	−0.02540	0.1010*
H23A	0.07850	−0.45360	−0.03130	0.1530*
H27C	0.09580	0.75920	0.15620	0.0860*	0.284 (5)
H27D	0.10430	0.67670	0.21690	0.0860*	0.284 (5)
H28D	0.18840	0.60140	0.19160	0.1680*	0.284 (5)
H28E	0.18470	0.78280	0.18820	0.1680*	0.284 (5)
H28F	0.18010	0.68320	0.13180	0.1680*	0.284 (5)
H1W	0.01850	0.74420	0.22660	0.2150*

	U11	U22	U33	U12	U13	U23
O1	0.0591 (9)	0.1313 (14)	0.0581 (8)	0.0294 (9)	−0.0094 (7)	−0.0096 (8)
O2	0.0594 (8)	0.1200 (13)	0.0496 (8)	0.0294 (8)	−0.0052 (6)	0.0052 (8)
O3	0.0572 (9)	0.1244 (14)	0.0903 (11)	−0.0163 (9)	0.0193 (8)	−0.0238 (10)
O4	0.0681 (9)	0.0813 (10)	0.0693 (9)	−0.0021 (8)	0.0110 (7)	−0.0154 (8)
O5	0.1437 (17)	0.0679 (11)	0.1328 (17)	−0.0098 (12)	0.0121 (14)	−0.0171 (11)
O6	0.0896 (12)	0.0735 (10)	0.1188 (14)	−0.0290 (9)	−0.0366 (10)	0.0151 (9)
N1	0.0445 (8)	0.0724 (11)	0.0672 (10)	−0.0046 (8)	0.0017 (7)	−0.0069 (8)
C1	0.0518 (11)	0.0847 (14)	0.0578 (12)	−0.0103 (10)	−0.0103 (9)	0.0094 (10)
C2	0.0859 (17)	0.139 (2)	0.0634 (15)	0.0026 (16)	−0.0145 (12)	−0.0060 (15)
C3	0.114 (2)	0.151 (3)	0.0594 (15)	−0.025 (2)	−0.0245 (15)	0.0058 (16)
C4	0.0914 (19)	0.105 (2)	0.095 (2)	−0.0268 (16)	−0.0439 (16)	0.0313 (16)
C5	0.0811 (16)	0.0976 (19)	0.102 (2)	0.0023 (14)	−0.0309 (14)	0.0253 (16)
C6	0.0664 (13)	0.0879 (16)	0.0727 (14)	0.0054 (12)	−0.0143 (11)	0.0142 (12)
C7	0.0486 (10)	0.0906 (15)	0.0586 (12)	0.0048 (10)	−0.0059 (9)	0.0010 (10)
C8	0.0473 (10)	0.0794 (14)	0.0559 (11)	0.0081 (9)	−0.0033 (8)	0.0072 (10)
C9	0.0471 (10)	0.0817 (14)	0.0516 (11)	0.0034 (10)	−0.0039 (8)	0.0038 (10)
C10	0.0518 (11)	0.0883 (14)	0.0443 (10)	0.0166 (10)	−0.0059 (8)	0.0008 (10)
C11	0.0454 (11)	0.129 (2)	0.0627 (13)	−0.0076 (12)	−0.0089 (9)	0.0161 (13)
C12	0.0529 (11)	0.1111 (18)	0.0601 (12)	−0.0177 (11)	−0.0072 (9)	0.0241 (12)
C13	0.0466 (9)	0.0619 (11)	0.0440 (9)	−0.0036 (8)	−0.0032 (7)	0.0011 (8)
C14	0.0469 (9)	0.0667 (12)	0.0481 (10)	−0.0043 (8)	−0.0025 (8)	0.0009 (9)
C15	0.0597 (12)	0.0736 (13)	0.0459 (10)	0.0013 (9)	0.0017 (8)	0.0070 (9)
C16	0.0486 (10)	0.0658 (12)	0.0450 (9)	−0.0115 (9)	−0.0052 (7)	0.0077 (8)
C17	0.0606 (11)	0.0602 (11)	0.0444 (9)	−0.0046 (9)	−0.0136 (8)	0.0061 (8)
C18	0.0618 (12)	0.0621 (12)	0.0501 (10)	0.0050 (9)	−0.0097 (8)	0.0007 (9)
C19	0.0493 (10)	0.0658 (12)	0.0454 (9)	−0.0039 (9)	−0.0034 (8)	0.0000 (8)
C20	0.0476 (10)	0.0656 (12)	0.0393 (9)	−0.0069 (8)	−0.0048 (7)	0.0035 (8)
C21	0.0536 (11)	0.0802 (14)	0.0426 (10)	−0.0034 (10)	−0.0036 (8)	0.0012 (9)
C22	0.0838 (15)	0.1019 (18)	0.0666 (13)	0.0154 (14)	0.0085 (11)	−0.0132 (13)
C23	0.135 (2)	0.0873 (18)	0.0831 (17)	0.0083 (17)	0.0029 (16)	−0.0220 (14)
C24	0.0535 (11)	0.0794 (14)	0.0772 (14)	−0.0121 (10)	−0.0018 (10)	−0.0123 (11)
C25	0.0754 (15)	0.0865 (17)	0.0900 (16)	0.0186 (12)	−0.0045 (12)	−0.0134 (13)
C26	0.0996 (18)	0.0606 (14)	0.0589 (12)	−0.0084 (13)	−0.0206 (12)	0.0097 (10)
C27A	0.083 (4)	0.076 (3)	0.113 (4)	−0.016 (3)	0.000 (2)	−0.011 (3)
C28A	0.098 (3)	0.097 (3)	0.136 (4)	−0.003 (2)	−0.044 (3)	−0.029 (3)
C28B	0.098 (3)	0.097 (3)	0.136 (4)	−0.003 (2)	−0.044 (3)	−0.029 (3)
C27B	0.076 (7)	0.059 (6)	0.081 (7)	−0.015 (5)	0.003 (5)	−0.012 (5)
O1W	0.179 (8)	0.082 (2)	0.175 (8)	0.041 (3)	0.095 (6)	0.024 (3)

O1—C9	1.193 (3)	C20—C21	1.459 (3)
O2—C9	1.348 (2)	C22—C23	1.486 (4)
O2—C10	1.413 (2)	C27A—C28A	1.491 (7)
O3—C21	1.198 (3)	C27B—C28B	1.479 (18)
O4—C21	1.332 (3)	C2—H2	0.9300
O4—C22	1.443 (3)	C3—H3	0.9300
O5—C26	1.196 (3)	C4—H4	0.9300
O6—C26	1.343 (3)	C5—H5	0.9300
O6—C27A	1.433 (5)	C6—H6	0.9300
O6—C27B	1.637 (11)	C7—H7	0.9300
O1W—H1W	1.0400	C8—H8	0.9300
O1W—H1Wi	1.1500	C11—H11	0.9300
N1—C19	1.376 (2)	C12—H12	0.9300
N1—C18	1.372 (2)	C14—H14	0.9300
N1—H1N	0.867 (15)	C15—H15	0.9300
C1—C2	1.374 (3)	C16—H16	0.9800
C1—C7	1.466 (3)	C22—H22B	0.9700
C1—C6	1.377 (3)	C22—H22A	0.9700
C2—C3	1.390 (4)	C23—H23A	0.9600
C3—C4	1.365 (5)	C23—H23B	0.9600
C4—C5	1.349 (4)	C23—H23C	0.9600
C5—C6	1.363 (4)	C24—H24A	0.9600
C7—C8	1.300 (3)	C24—H24C	0.9600
C8—C9	1.457 (3)	C24—H24B	0.9600
C10—C15	1.358 (3)	C25—H25B	0.9600
C10—C11	1.362 (3)	C25—H25C	0.9600
C11—C12	1.377 (3)	C25—H25A	0.9600
C12—C13	1.377 (3)	C27A—H27A	0.9700
C13—C16	1.526 (2)	C27A—H27B	0.9700
C13—C14	1.370 (2)	C27B—H27C	0.9700
C14—C15	1.382 (2)	C27B—H27D	0.9700
C16—C17	1.511 (2)	C28A—H28A	0.9600
C16—C20	1.516 (2)	C28A—H28B	0.9600
C17—C26	1.451 (3)	C28A—H28C	0.9600
C17—C18	1.348 (3)	C28B—H28F	0.9600
C18—C25	1.494 (3)	C28B—H28D	0.9600
C19—C24	1.498 (3)	C28B—H28E	0.9600
C19—C20	1.349 (3)
C9—O2—C10	118.53 (16)	C5—C6—H6	120.00
C21—O4—C22	118.05 (16)	C1—C6—H6	120.00
C26—O6—C27A	123.3 (3)	C8—C7—H7	116.00
C26—O6—C27B	96.1 (5)	C1—C7—H7	116.00
H1W—O1W—H1Wi	84.00	C7—C8—H8	119.00
C18—N1—C19	124.16 (16)	C9—C8—H8	119.00
C18—N1—H1N	116.3 (12)	C12—C11—H11	120.00
C19—N1—H1N	117.7 (12)	C10—C11—H11	120.00
C2—C1—C6	118.4 (2)	C11—C12—H12	119.00
C6—C1—C7	122.35 (19)	C13—C12—H12	119.00
C2—C1—C7	119.3 (2)	C15—C14—H14	119.00
C1—C2—C3	120.2 (3)	C13—C14—H14	119.00
C2—C3—C4	119.9 (3)	C10—C15—H15	120.00
C3—C4—C5	119.7 (3)	C14—C15—H15	120.00
C4—C5—C6	121.0 (3)	C13—C16—H16	108.00
C1—C6—C5	120.8 (2)	C17—C16—H16	108.00
C1—C7—C8	127.62 (19)	C20—C16—H16	108.00
C7—C8—C9	122.47 (18)	O4—C22—H22B	110.00
O2—C9—C8	110.62 (16)	C23—C22—H22A	111.00
O1—C9—C8	126.50 (18)	C23—C22—H22B	111.00
O1—C9—O2	122.88 (17)	H22A—C22—H22B	109.00
O2—C10—C11	117.00 (17)	O4—C22—H22A	110.00
O2—C10—C15	121.74 (18)	C22—C23—H23A	109.00
C11—C10—C15	121.16 (18)	C22—C23—H23B	109.00
C10—C11—C12	119.12 (19)	H23A—C23—H23B	110.00
C11—C12—C13	121.3 (2)	H23A—C23—H23C	109.00
C12—C13—C16	121.50 (16)	H23B—C23—H23C	109.00
C14—C13—C16	120.58 (15)	C22—C23—H23C	110.00
C12—C13—C14	117.92 (17)	C19—C24—H24B	109.00
C13—C14—C15	121.38 (16)	C19—C24—H24C	109.00
C10—C15—C14	119.08 (17)	C19—C24—H24A	109.00
C13—C16—C20	110.39 (14)	H24A—C24—H24C	109.00
C17—C16—C20	111.40 (15)	H24B—C24—H24C	110.00
C13—C16—C17	111.11 (13)	H24A—C24—H24B	109.00
C18—C17—C26	120.53 (18)	C18—C25—H25B	109.00
C16—C17—C26	118.71 (17)	C18—C25—H25C	109.00
C16—C17—C18	120.67 (16)	C18—C25—H25A	110.00
N1—C18—C17	119.24 (17)	H25A—C25—H25C	110.00
N1—C18—C25	112.71 (18)	H25B—C25—H25C	109.00
C17—C18—C25	128.05 (17)	H25A—C25—H25B	109.00
C20—C19—C24	128.45 (17)	O6—C27A—H27B	110.00
N1—C19—C24	112.67 (16)	C28A—C27A—H27A	110.00
N1—C19—C20	118.88 (16)	C28A—C27A—H27B	110.00
C16—C20—C19	120.87 (15)	H27A—C27A—H27B	108.00
C16—C20—C21	113.91 (16)	O6—C27A—H27A	110.00
C19—C20—C21	125.15 (17)	O6—C27B—H27D	113.00
O3—C21—O4	121.8 (2)	C28B—C27B—H27C	113.00
O3—C21—C20	123.6 (2)	H27C—C27B—H27D	110.00
O4—C21—C20	114.70 (17)	O6—C27B—H27C	113.00
O4—C22—C23	106.29 (19)	C28B—C27B—H27D	113.00
O5—C26—C17	126.6 (3)	H28A—C28A—H28C	109.00
O5—C26—O6	121.0 (2)	H28B—C28A—H28C	109.00
O6—C26—C17	112.4 (2)	C27A—C28A—H28A	109.00
O6—C27A—C28A	107.5 (4)	C27A—C28A—H28B	110.00
O6—C27B—C28B	95.7 (8)	H28A—C28A—H28B	109.00
C3—C2—H2	120.00	C27A—C28A—H28C	110.00
C1—C2—H2	120.00	C27B—C28B—H28E	110.00
C2—C3—H3	120.00	C27B—C28B—H28F	110.00
C4—C3—H3	120.00	C27B—C28B—H28D	109.00
C5—C4—H4	120.00	H28D—C28B—H28F	109.00
C3—C4—H4	120.00	H28E—C28B—H28F	109.00
C4—C5—H5	120.00	H28D—C28B—H28E	109.00
C6—C5—H5	119.00
C10—O2—C9—O1	3.9 (3)	C11—C12—C13—C16	177.6 (2)
C10—O2—C9—C8	−176.27 (18)	C12—C13—C14—C15	0.7 (3)
C9—O2—C10—C11	119.8 (2)	C16—C13—C14—C15	−178.96 (16)
C9—O2—C10—C15	−63.7 (3)	C12—C13—C16—C17	−107.2 (2)
C22—O4—C21—O3	−0.8 (3)	C12—C13—C16—C20	128.71 (19)
C22—O4—C21—C20	179.46 (16)	C14—C13—C16—C17	72.5 (2)
C21—O4—C22—C23	−179.81 (18)	C14—C13—C16—C20	−51.6 (2)
C27A—O6—C26—O5	6.0 (4)	C13—C14—C15—C10	1.0 (3)
C27A—O6—C26—C17	−175.4 (3)	C13—C16—C17—C18	−101.32 (19)
C26—O6—C27A—C28A	89.2 (4)	C13—C16—C17—C26	75.0 (2)
C19—N1—C18—C17	−10.2 (3)	C20—C16—C17—C18	22.2 (2)
C19—N1—C18—C25	169.52 (18)	C20—C16—C17—C26	−161.42 (16)
C18—N1—C19—C20	11.1 (3)	C13—C16—C20—C19	102.65 (18)
C18—N1—C19—C24	−169.25 (17)	C13—C16—C20—C21	−74.51 (18)
C6—C1—C2—C3	0.6 (4)	C17—C16—C20—C19	−21.3 (2)
C7—C1—C2—C3	178.7 (3)	C17—C16—C20—C21	161.55 (15)
C2—C1—C6—C5	−0.1 (4)	C16—C17—C18—N1	−8.0 (3)
C7—C1—C6—C5	−178.1 (2)	C16—C17—C18—C25	172.33 (19)
C2—C1—C7—C8	178.2 (3)	C26—C17—C18—N1	175.67 (17)
C6—C1—C7—C8	−3.8 (4)	C26—C17—C18—C25	−4.0 (3)
C1—C2—C3—C4	−0.7 (5)	C16—C17—C26—O5	−177.1 (2)
C2—C3—C4—C5	0.3 (5)	C16—C17—C26—O6	4.4 (3)
C3—C4—C5—C6	0.3 (5)	C18—C17—C26—O5	−0.7 (3)
C4—C5—C6—C1	−0.4 (4)	C18—C17—C26—O6	−179.25 (18)
C1—C7—C8—C9	177.9 (2)	N1—C19—C20—C16	6.2 (2)
C7—C8—C9—O1	−3.8 (4)	N1—C19—C20—C21	−177.00 (17)
C7—C8—C9—O2	176.4 (2)	C24—C19—C20—C16	−173.42 (17)
O2—C10—C11—C12	176.5 (2)	C24—C19—C20—C21	3.4 (3)
C15—C10—C11—C12	0.1 (4)	C16—C20—C21—O3	−9.3 (3)
O2—C10—C15—C14	−177.68 (18)	C16—C20—C21—O4	170.37 (15)
C11—C10—C15—C14	−1.4 (3)	C19—C20—C21—O3	173.65 (19)
C10—C11—C12—C13	1.8 (4)	C19—C20—C21—O4	−6.7 (3)
C11—C12—C13—C14	−2.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (2)	2.31 (2)	3.148 (2)	163 (2)
O1W—H1W···O5	1.04	1.81	2.615 (6)	132
C14—H14···O1Wii	0.93	2.50	3.140 (6)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (2)	2.31 (2)	3.148 (2)	163 (2)
O1W—H1W⋯O5	1.04	1.81	2.615 (6)	132
C14—H14⋯O1W ii	0.93	2.50	3.140 (6)	126

Symmetry codes: (i) ; (ii) .