Ethyl 4-hydr-oxy-1-(2-morpholinopro-pano-yl)-2,6-diphenyl-1,2,5,6-tetra-hydro-pyridin-3-carboxyl-ate.

In the title compound, C(27)H(32)N(2)O(5), the morpholine ring adopts a chair conformation with two C atoms deviating by -0.656 (4) and 0.679 (3) Å from the least-squares plane defined by the rest of atoms in the ring. The tetra-hydro-pyridine ring adopts a half-chair conformation. The mol-ecular structure is stabilized by a strong intra-molecular O-H⋯O inter-action, generating an S(6) motif. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, generating a C(7) chain along the a axis, and R(2) (2)(20) and R(4) (4)(20) graph-set motifs.

Related literature

For related structures, see: Aridoss et al. (2009a ▶,b ▶); Gayathri et al. (2008 ▶); Kavitha et al. (2007 ▶); Ramachandran et al. (2008 ▶); Subha Nandhini et al. (2003 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C27H32N2O5

M = 464.55

Monoclinic,

a = 8.2251 (2) Å

b = 10.6219 (4) Å

c = 28.7046 (10) Å

β = 92.375 (2)°

V = 2505.66 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (; Bruker 1999 ▶) T min = 0.975, T max = 0.983

22895 measured reflections

4850 independent reflections

3353 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.02

4850 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050259/is2497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050259/is2497Isup2.hkl

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

C27H32N2O5	F(000) = 992
Mr = 464.55	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5113 reflections
a = 8.2251 (2) Å	θ = 2.4–23.3°
b = 10.6219 (4) Å	µ = 0.09 mm−1
c = 28.7046 (10) Å	T = 293 K
β = 92.375 (2)°	Block, colourless
V = 2505.66 (14) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4850 independent reflections
Radiation source: fine-focus sealed tube	3353 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω and φ scan	θmax = 25.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −10→9
Tmin = 0.975, Tmax = 0.983	k = −13→12
22895 measured reflections	l = −35→35

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0554P)2 + 1.1339P] where P = (Fo2 + 2Fc2)/3
4850 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 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	−0.09176 (19)	0.60293 (18)	0.27695 (5)	0.0644 (5)
N2	0.2969 (2)	0.54061 (17)	0.28207 (6)	0.0498 (5)
C1	0.2028 (2)	0.6983 (2)	0.36715 (7)	0.0444 (5)
H1A	0.2803	0.7179	0.3432	0.053*
C2	0.2787 (3)	0.5948 (2)	0.39704 (8)	0.0509 (5)
H2A	0.3412	0.5401	0.3775	0.061*
H2B	0.3535	0.6323	0.4201	0.061*
O2	0.4987 (2)	0.32639 (18)	0.27766 (9)	0.0972 (7)
O3	0.2277 (2)	0.44389 (18)	0.45418 (6)	0.0688 (5)
H3A	0.1594	0.3950	0.4637	0.118 (15)*
C3	0.1586 (3)	0.5184 (2)	0.42121 (7)	0.0502 (5)
O4	−0.0581 (2)	0.36103 (18)	0.46520 (6)	0.0758 (5)
C4	−0.0018 (3)	0.5187 (2)	0.40991 (7)	0.0491 (5)
O5	−0.2586 (2)	0.43166 (18)	0.41704 (7)	0.0763 (5)
C5	−0.0748 (2)	0.6014 (2)	0.37157 (7)	0.0445 (5)
H5A	−0.1409	0.5455	0.3513	0.053*
N1	0.05448 (19)	0.65010 (16)	0.34259 (5)	0.0433 (4)
C6	0.0380 (3)	0.6339 (2)	0.29554 (7)	0.0486 (5)
C7	0.1903 (3)	0.6443 (2)	0.26673 (7)	0.0509 (5)
H7A	0.2453	0.7233	0.2753	0.061*
C8	0.2302 (3)	0.4162 (2)	0.27172 (10)	0.0669 (7)
H8A	0.2218	0.4036	0.2382	0.080*
H8B	0.1219	0.4096	0.2837	0.080*
C9	0.3375 (3)	0.3183 (3)	0.29354 (13)	0.0853 (9)
H9A	0.3400	0.3282	0.3272	0.102*
H9B	0.2933	0.2356	0.2861	0.102*
C10	0.5629 (3)	0.4474 (3)	0.28766 (12)	0.0811 (9)
H10A	0.6724	0.4527	0.2765	0.097*
H10B	0.5690	0.4600	0.3212	0.097*
C11	0.4610 (3)	0.5486 (2)	0.26541 (9)	0.0634 (7)
H11A	0.5074	0.6303	0.2731	0.076*
H11B	0.4584	0.5390	0.2318	0.076*
C12	−0.1901 (2)	0.7031 (2)	0.38781 (7)	0.0454 (5)
C13	−0.2138 (3)	0.7287 (3)	0.43393 (8)	0.0654 (7)
H13A	−0.1534	0.6855	0.4569	0.078*
C14	−0.3262 (3)	0.8179 (3)	0.44672 (11)	0.0777 (8)
H14A	−0.3411	0.8335	0.4781	0.093*
C15	−0.4147 (3)	0.8827 (3)	0.41383 (12)	0.0761 (8)
H15A	−0.4900	0.9427	0.4225	0.091*
C16	−0.3922 (3)	0.8588 (3)	0.36786 (12)	0.0791 (8)
H16A	−0.4518	0.9034	0.3451	0.095*
C17	−0.2821 (3)	0.7691 (3)	0.35491 (9)	0.0647 (7)
H17A	−0.2696	0.7528	0.3234	0.078*
C18	0.1703 (2)	0.8208 (2)	0.39239 (7)	0.0456 (5)
C19	0.1431 (3)	0.9284 (2)	0.36661 (9)	0.0683 (7)
H19A	0.1400	0.9239	0.3342	0.082*
C20	0.1205 (4)	1.0428 (3)	0.38800 (12)	0.0894 (10)
H20A	0.1021	1.1148	0.3701	0.107*
C21	0.1254 (4)	1.0502 (3)	0.43555 (12)	0.0841 (9)
H21A	0.1099	1.1274	0.4500	0.101*
C22	0.1524 (3)	0.9460 (3)	0.46159 (9)	0.0727 (8)
H22A	0.1563	0.9515	0.4940	0.087*
C23	0.1744 (3)	0.8312 (2)	0.44022 (8)	0.0577 (6)
H23A	0.1923	0.7598	0.4584	0.069*
C24	0.1449 (3)	0.6501 (3)	0.21484 (8)	0.0750 (8)
H24A	0.2419	0.6567	0.1976	0.113*
H24B	0.0771	0.7222	0.2086	0.113*
H24C	0.0870	0.5750	0.2057	0.113*
C25	−0.1051 (3)	0.4311 (2)	0.43333 (9)	0.0593 (6)
C26	−0.3741 (4)	0.3489 (3)	0.43944 (13)	0.0938 (10)
H26A	−0.3403	0.3369	0.4719	0.113*
H26B	−0.4810	0.3875	0.4383	0.113*
C27	−0.3819 (6)	0.2296 (4)	0.41630 (19)	0.1500 (18)
H27A	−0.4578	0.1761	0.4313	0.225*
H27B	−0.2762	0.1912	0.4177	0.225*
H27C	−0.4169	0.2416	0.3843	0.225*

	U11	U22	U33	U12	U13	U23
O1	0.0516 (9)	0.0898 (13)	0.0509 (9)	−0.0112 (9)	−0.0078 (7)	−0.0060 (8)
N2	0.0478 (10)	0.0492 (11)	0.0528 (10)	−0.0081 (8)	0.0058 (8)	−0.0110 (8)
C1	0.0400 (11)	0.0524 (13)	0.0408 (10)	−0.0027 (9)	0.0002 (8)	−0.0027 (9)
C2	0.0457 (12)	0.0547 (13)	0.0518 (12)	0.0047 (10)	−0.0029 (9)	−0.0057 (10)
O2	0.0619 (12)	0.0616 (12)	0.169 (2)	0.0010 (9)	0.0195 (12)	−0.0312 (13)
O3	0.0628 (10)	0.0734 (12)	0.0696 (11)	0.0181 (10)	−0.0053 (9)	0.0206 (9)
C3	0.0548 (13)	0.0490 (13)	0.0466 (12)	0.0115 (10)	−0.0001 (10)	−0.0004 (10)
O4	0.0742 (12)	0.0752 (12)	0.0780 (12)	0.0057 (10)	0.0046 (9)	0.0336 (10)
C4	0.0472 (12)	0.0507 (13)	0.0493 (12)	0.0049 (10)	0.0022 (9)	0.0051 (10)
O5	0.0573 (10)	0.0811 (13)	0.0902 (13)	−0.0100 (9)	0.0009 (9)	0.0335 (10)
C5	0.0411 (11)	0.0482 (12)	0.0438 (11)	−0.0037 (9)	−0.0013 (9)	0.0040 (9)
N1	0.0397 (9)	0.0502 (10)	0.0399 (9)	−0.0025 (8)	−0.0006 (7)	−0.0016 (8)
C6	0.0494 (12)	0.0520 (13)	0.0439 (11)	−0.0026 (10)	−0.0020 (9)	−0.0026 (10)
C7	0.0557 (13)	0.0551 (14)	0.0420 (11)	−0.0060 (11)	0.0029 (9)	−0.0028 (10)
C8	0.0549 (14)	0.0582 (15)	0.0883 (18)	−0.0127 (12)	0.0102 (13)	−0.0190 (14)
C9	0.0709 (18)	0.0493 (16)	0.137 (3)	−0.0089 (13)	0.0176 (18)	−0.0140 (17)
C10	0.0524 (15)	0.0664 (18)	0.125 (3)	−0.0077 (13)	0.0122 (15)	−0.0193 (17)
C11	0.0523 (13)	0.0639 (16)	0.0748 (16)	−0.0151 (12)	0.0146 (12)	−0.0146 (13)
C12	0.0364 (10)	0.0493 (12)	0.0505 (12)	−0.0039 (9)	0.0012 (9)	0.0070 (10)
C13	0.0607 (14)	0.0823 (18)	0.0530 (13)	0.0145 (13)	−0.0005 (11)	−0.0028 (13)
C14	0.0641 (16)	0.093 (2)	0.0767 (18)	0.0074 (16)	0.0106 (14)	−0.0208 (16)
C15	0.0513 (15)	0.0607 (17)	0.117 (3)	0.0051 (12)	0.0178 (15)	−0.0037 (17)
C16	0.0612 (16)	0.078 (2)	0.099 (2)	0.0209 (14)	0.0122 (15)	0.0306 (17)
C17	0.0573 (14)	0.0737 (17)	0.0636 (15)	0.0108 (13)	0.0070 (11)	0.0185 (13)
C18	0.0378 (11)	0.0509 (13)	0.0476 (12)	−0.0014 (9)	−0.0027 (9)	−0.0040 (10)
C19	0.0879 (19)	0.0577 (16)	0.0577 (14)	0.0038 (13)	−0.0153 (13)	−0.0019 (12)
C20	0.118 (3)	0.0547 (17)	0.093 (2)	0.0152 (16)	−0.0289 (19)	−0.0008 (16)
C21	0.091 (2)	0.0642 (19)	0.095 (2)	0.0138 (16)	−0.0131 (17)	−0.0268 (17)
C22	0.0827 (19)	0.075 (2)	0.0602 (15)	0.0021 (15)	0.0043 (13)	−0.0204 (15)
C23	0.0636 (14)	0.0596 (15)	0.0502 (13)	−0.0008 (12)	0.0064 (11)	−0.0055 (11)
C24	0.0797 (18)	0.101 (2)	0.0441 (13)	−0.0055 (16)	0.0046 (12)	0.0004 (14)
C25	0.0559 (14)	0.0597 (15)	0.0625 (14)	0.0066 (12)	0.0047 (11)	0.0135 (12)
C26	0.0666 (18)	0.096 (3)	0.119 (3)	−0.0084 (17)	0.0110 (17)	0.041 (2)
C27	0.161 (4)	0.083 (3)	0.206 (5)	−0.035 (3)	0.016 (4)	0.014 (3)

O1—C6	1.219 (2)	C10—H10B	0.9700
N2—C11	1.453 (3)	C11—H11A	0.9700
N2—C8	1.457 (3)	C11—H11B	0.9700
N2—C7	1.464 (3)	C12—C13	1.373 (3)
C1—N1	1.475 (2)	C12—C17	1.377 (3)
C1—C2	1.513 (3)	C13—C14	1.384 (4)
C1—C18	1.518 (3)	C13—H13A	0.9300
C1—H1A	0.9800	C14—C15	1.356 (4)
C2—C3	1.474 (3)	C14—H14A	0.9300
C2—H2A	0.9700	C15—C16	1.364 (4)
C2—H2B	0.9700	C15—H15A	0.9300
O2—C10	1.414 (3)	C16—C17	1.376 (4)
O2—C9	1.423 (3)	C16—H16A	0.9300
O3—C3	1.342 (3)	C17—H17A	0.9300
O3—H3A	0.8200	C18—C19	1.375 (3)
C3—C4	1.345 (3)	C18—C23	1.376 (3)
O4—C25	1.229 (3)	C19—C20	1.378 (4)
C4—C25	1.445 (3)	C19—H19A	0.9300
C4—C5	1.513 (3)	C20—C21	1.366 (4)
O5—C25	1.328 (3)	C20—H20A	0.9300
O5—C26	1.463 (3)	C21—C22	1.349 (4)
C5—N1	1.471 (2)	C21—H21A	0.9300
C5—C12	1.524 (3)	C22—C23	1.380 (3)
C5—H5A	0.9800	C22—H22A	0.9300
N1—C6	1.363 (3)	C23—H23A	0.9300
C6—C7	1.533 (3)	C24—H24A	0.9600
C7—C24	1.522 (3)	C24—H24B	0.9600
C7—H7A	0.9800	C24—H24C	0.9600
C8—C9	1.486 (4)	C26—C27	1.430 (5)
C8—H8A	0.9700	C26—H26A	0.9700
C8—H8B	0.9700	C26—H26B	0.9700
C9—H9A	0.9700	C27—H27A	0.9600
C9—H9B	0.9700	C27—H27B	0.9600
C10—C11	1.491 (4)	C27—H27C	0.9600
C10—H10A	0.9700
C11—N2—C8	109.46 (18)	C10—C11—H11A	109.8
C11—N2—C7	114.22 (18)	N2—C11—H11B	109.8
C8—N2—C7	113.89 (18)	C10—C11—H11B	109.8
N1—C1—C2	109.42 (17)	H11A—C11—H11B	108.3
N1—C1—C18	111.54 (16)	C13—C12—C17	117.7 (2)
C2—C1—C18	115.37 (17)	C13—C12—C5	123.4 (2)
N1—C1—H1A	106.7	C17—C12—C5	118.8 (2)
C2—C1—H1A	106.7	C12—C13—C14	120.9 (2)
C18—C1—H1A	106.7	C12—C13—H13A	119.5
C3—C2—C1	113.42 (17)	C14—C13—H13A	119.5
C3—C2—H2A	108.9	C15—C14—C13	120.6 (3)
C1—C2—H2A	108.9	C15—C14—H14A	119.7
C3—C2—H2B	108.9	C13—C14—H14A	119.7
C1—C2—H2B	108.9	C14—C15—C16	119.3 (3)
H2A—C2—H2B	107.7	C14—C15—H15A	120.4
C10—O2—C9	109.6 (2)	C16—C15—H15A	120.4
C3—O3—H3A	109.5	C15—C16—C17	120.5 (3)
O3—C3—C4	123.6 (2)	C15—C16—H16A	119.8
O3—C3—C2	112.59 (19)	C17—C16—H16A	119.8
C4—C3—C2	123.7 (2)	C12—C17—C16	121.1 (2)
C3—C4—C25	118.4 (2)	C12—C17—H17A	119.5
C3—C4—C5	122.17 (19)	C16—C17—H17A	119.5
C25—C4—C5	119.27 (19)	C19—C18—C23	117.8 (2)
C25—O5—C26	117.9 (2)	C19—C18—C1	118.91 (19)
N1—C5—C4	109.94 (16)	C23—C18—C1	123.2 (2)
N1—C5—C12	113.43 (17)	C18—C19—C20	121.0 (2)
C4—C5—C12	114.99 (17)	C18—C19—H19A	119.5
N1—C5—H5A	105.9	C20—C19—H19A	119.5
C4—C5—H5A	105.9	C21—C20—C19	119.8 (3)
C12—C5—H5A	105.9	C21—C20—H20A	120.1
C6—N1—C5	118.14 (16)	C19—C20—H20A	120.1
C6—N1—C1	124.31 (17)	C22—C21—C20	120.2 (3)
C5—N1—C1	117.05 (15)	C22—C21—H21A	119.9
O1—C6—N1	121.15 (19)	C20—C21—H21A	119.9
O1—C6—C7	120.23 (19)	C21—C22—C23	120.0 (3)
N1—C6—C7	118.41 (18)	C21—C22—H22A	120.0
N2—C7—C24	116.4 (2)	C23—C22—H22A	120.0
N2—C7—C6	106.06 (17)	C18—C23—C22	121.1 (2)
C24—C7—C6	110.97 (18)	C18—C23—H23A	119.5
N2—C7—H7A	107.7	C22—C23—H23A	119.5
C24—C7—H7A	107.7	C7—C24—H24A	109.5
C6—C7—H7A	107.7	C7—C24—H24B	109.5
N2—C8—C9	109.7 (2)	H24A—C24—H24B	109.5
N2—C8—H8A	109.7	C7—C24—H24C	109.5
C9—C8—H8A	109.7	H24A—C24—H24C	109.5
N2—C8—H8B	109.7	H24B—C24—H24C	109.5
C9—C8—H8B	109.7	O4—C25—O5	122.0 (2)
H8A—C8—H8B	108.2	O4—C25—C4	124.3 (2)
O2—C9—C8	111.6 (2)	O5—C25—C4	113.7 (2)
O2—C9—H9A	109.3	C27—C26—O5	110.2 (3)
C8—C9—H9A	109.3	C27—C26—H26A	109.6
O2—C9—H9B	109.3	O5—C26—H26A	109.6
C8—C9—H9B	109.3	C27—C26—H26B	109.6
H9A—C9—H9B	108.0	O5—C26—H26B	109.6
O2—C10—C11	111.7 (2)	H26A—C26—H26B	108.1
O2—C10—H10A	109.3	C26—C27—H27A	109.5
C11—C10—H10A	109.3	C26—C27—H27B	109.5
O2—C10—H10B	109.3	H27A—C27—H27B	109.5
C11—C10—H10B	109.3	C26—C27—H27C	109.5
H10A—C10—H10B	107.9	H27A—C27—H27C	109.5
N2—C11—C10	109.3 (2)	H27B—C27—H27C	109.5
N2—C11—H11A	109.8
N1—C1—C2—C3	−40.7 (2)	C9—O2—C10—C11	−58.4 (3)
C18—C1—C2—C3	86.0 (2)	C8—N2—C11—C10	−57.6 (3)
C1—C2—C3—O3	−167.93 (18)	C7—N2—C11—C10	173.3 (2)
C1—C2—C3—C4	15.2 (3)	O2—C10—C11—N2	58.9 (3)
O3—C3—C4—C25	−2.2 (3)	N1—C5—C12—C13	−120.7 (2)
C2—C3—C4—C25	174.4 (2)	C4—C5—C12—C13	7.0 (3)
O3—C3—C4—C5	−178.2 (2)	N1—C5—C12—C17	62.6 (3)
C2—C3—C4—C5	−1.6 (3)	C4—C5—C12—C17	−169.6 (2)
C3—C4—C5—N1	14.9 (3)	C17—C12—C13—C14	0.0 (4)
C25—C4—C5—N1	−161.11 (19)	C5—C12—C13—C14	−176.7 (2)
C3—C4—C5—C12	−114.6 (2)	C12—C13—C14—C15	−0.5 (4)
C25—C4—C5—C12	69.4 (3)	C13—C14—C15—C16	0.2 (4)
C4—C5—N1—C6	127.7 (2)	C14—C15—C16—C17	0.6 (4)
C12—C5—N1—C6	−102.0 (2)	C13—C12—C17—C16	0.9 (4)
C4—C5—N1—C1	−44.5 (2)	C5—C12—C17—C16	177.7 (2)
C12—C5—N1—C1	85.8 (2)	C15—C16—C17—C12	−1.2 (4)
C2—C1—N1—C6	−113.0 (2)	N1—C1—C18—C19	−71.5 (2)
C18—C1—N1—C6	118.1 (2)	C2—C1—C18—C19	162.9 (2)
C2—C1—N1—C5	58.7 (2)	N1—C1—C18—C23	111.8 (2)
C18—C1—N1—C5	−70.1 (2)	C2—C1—C18—C23	−13.8 (3)
C5—N1—C6—O1	14.1 (3)	C23—C18—C19—C20	−0.1 (4)
C1—N1—C6—O1	−174.3 (2)	C1—C18—C19—C20	−177.0 (3)
C5—N1—C6—C7	−160.63 (18)	C18—C19—C20—C21	0.2 (5)
C1—N1—C6—C7	11.0 (3)	C19—C20—C21—C22	0.1 (5)
C11—N2—C7—C24	67.5 (3)	C20—C21—C22—C23	−0.4 (5)
C8—N2—C7—C24	−59.3 (3)	C19—C18—C23—C22	−0.1 (3)
C11—N2—C7—C6	−168.57 (18)	C1—C18—C23—C22	176.6 (2)
C8—N2—C7—C6	64.6 (2)	C21—C22—C23—C18	0.4 (4)
O1—C6—C7—N2	−110.6 (2)	C26—O5—C25—O4	2.3 (4)
N1—C6—C7—N2	64.2 (2)	C26—O5—C25—C4	−178.2 (2)
O1—C6—C7—C24	16.7 (3)	C3—C4—C25—O4	4.8 (4)
N1—C6—C7—C24	−168.6 (2)	C5—C4—C25—O4	−179.1 (2)
C11—N2—C8—C9	57.5 (3)	C3—C4—C25—O5	−174.8 (2)
C7—N2—C8—C9	−173.2 (2)	C5—C4—C25—O5	1.4 (3)
C10—O2—C9—C8	58.0 (3)	C25—O5—C26—C27	−91.5 (4)
N2—C8—C9—O2	−58.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.83	2.542 (2)	145
C10—H10A···O1i	0.97	2.51	3.311 (3)	140
C11—H11A···O2ii	0.97	2.54	3.222 (3)	127
C26—H26B···O3iii	0.97	2.53	3.470 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.83	2.542 (2)	145
C10—H10A⋯O1i	0.97	2.51	3.311 (3)	140
C11—H11A⋯O2ii	0.97	2.54	3.222 (3)	127
C26—H26B⋯O3iii	0.97	2.53	3.470 (4)	163

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