(7R,8R,8aS)-8-Hydr-oxy-7-phenyl-per-hydro-indolizin-3-one.

The absolute configuration of the title compound, C(14)H(17)NO(2), was assigned from the synthesis. There are two mol-ecules in the asymmetric unit. Their geometries are very similar and corresponding bond lengths are almost identical [mean deviation for all non-H atoms = 0.015 (2) Å]. The six-membered ring of the indolizine system adopts a chair conformation. In the crystal structure, mol-ecules form chains parallel to the a axis via inter-molecular O-H⋯O hydrogen bonds, which help to stabilize the crystal structure.

Related literature

Polyhydroxy­lated indolizidine alkaloids are excellent inhibitors of biologically important pathways, see: Melo et al. (2006 ▶); Michael (2003 ▶); Lillelund et al. (2002 ▶); Gerber-Lemaire & Juillerat-Jeanneret (2006 ▶); Butters (2002 ▶); Compain & Martin (2001 ▶); Shi et al. (2008 ▶); Fujita et al. (2004 ▶). For indolizines as anti­mycobacterial agents against mycobacterial tuberculosis, see: Gundersen et al. (2003 ▶). For the biological activity of indolizine derivatives, see: Teklu et al. (2005 ▶); Foster et al. (1995 ▶). For their pharmacological applications, see: Couture et al. (2000 ▶); Jorgensen et al. (2000 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For conjugation of the lone-pair electrons in simple amides, see: Brown & Corbridge (1954 ▶); Pedersen (1967 ▶). For bond lengths and angles in related structures, see: Vrábel et al. (2004 ▶); Švorc et al. (2008 ▶). For the synthesis, see: Šafář et al. (2009 ▶).

Experimental

Crystal data

C14H17NO2

M = 231.29

Orthorhombic,

a = 25.3592 (4) Å

b = 16.1467 (2) Å

c = 6.0086 (1) Å

V = 2460.33 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.33 × 0.26 × 0.15 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.965, T max = 0.988

60218 measured reflections

3791 independent reflections

1856 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.097

S = 0.98

3791 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901085X/fj2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901085X/fj2203Isup2.hkl

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

C14H17NO2	F(000) = 992
Mr = 231.29	Dx = 1.249 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 19073 reflections
a = 25.3592 (4) Å	θ = 3.0–29.5°
b = 16.1467 (2) Å	µ = 0.08 mm−1
c = 6.0086 (1) Å	T = 298 K
V = 2460.33 (6) Å3	Block, white
Z = 8	0.33 × 0.26 × 0.15 mm

Oxford Diffraction Gemini R CCD diffractometer	3791 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 10.4340 pixels mm-1	θmax = 29.6°, θmin = 3.0°
Rotation method data acquisition using ω and φ scans	h = −34→34
Absorption correction: analytical (Clark & Reid, 1995)	k = −22→22
Tmin = 0.965, Tmax = 0.988	l = −8→8
60218 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3791 reflections	Δρmax = 0.12 e Å−3
311 parameters	Δρmin = −0.10 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (10)

Experimental. face-indexed (Oxford Diffraction, 2006)

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
C2	0.70322 (7)	0.68436 (12)	0.1107 (4)	0.0598 (5)
C3	0.74476 (8)	0.61874 (15)	0.0828 (4)	0.0771 (6)
H3A	0.7286	0.5657	0.0504	0.093*
H3B	0.7683	0.6330	−0.0384	0.093*
C4	0.77424 (8)	0.61487 (12)	0.2968 (4)	0.0741 (6)
H4A	0.8116	0.6233	0.2714	0.089*
H4B	0.7693	0.5614	0.3673	0.089*
C5	0.75196 (6)	0.68383 (11)	0.4430 (4)	0.0578 (5)
H5	0.7375	0.6596	0.5796	0.069*
C6	0.79146 (6)	0.75095 (10)	0.5042 (4)	0.0518 (5)
H6	0.8110	0.7671	0.3704	0.062*
C7	0.76420 (7)	0.82764 (11)	0.6015 (4)	0.0574 (5)
H7	0.7480	0.8109	0.7425	0.069*
C8	0.72007 (7)	0.85684 (11)	0.4495 (4)	0.0696 (6)
H8A	0.7351	0.8763	0.3105	0.083*
H8B	0.7020	0.9031	0.5189	0.083*
C9	0.68041 (7)	0.78853 (12)	0.4007 (4)	0.0741 (6)
H9A	0.6622	0.7728	0.5361	0.089*
H9B	0.6545	0.8078	0.2938	0.089*
C10	0.80442 (7)	0.89421 (12)	0.6548 (4)	0.0609 (5)
C11	0.82924 (9)	0.89602 (15)	0.8595 (4)	0.0796 (6)
H11	0.8201	0.8570	0.9667	0.096*
C12	0.86719 (10)	0.95414 (18)	0.9085 (5)	0.0986 (9)
H12	0.8834	0.9539	1.0473	0.118*
C13	0.88119 (10)	1.01244 (18)	0.7536 (6)	0.1037 (10)
H13	0.9069	1.0516	0.7867	0.124*
C14	0.85711 (10)	1.01259 (15)	0.5506 (5)	0.0936 (8)
H14	0.8661	1.0524	0.4453	0.112*
C15	0.81908 (8)	0.95311 (13)	0.5012 (4)	0.0774 (6)
H15	0.8033	0.9532	0.3615	0.093*
C16	1.04902 (7)	0.19922 (13)	1.4431 (4)	0.0621 (5)
C17	1.01297 (9)	0.12496 (14)	1.4512 (5)	0.0835 (7)
H17A	1.0321	0.0762	1.4999	0.100*
H17B	0.9839	0.1347	1.5528	0.100*
C18	0.99320 (11)	0.11388 (12)	1.2193 (4)	0.0875 (7)
H18A	0.9552	0.1074	1.2189	0.105*
H18B	1.0089	0.0651	1.1520	0.105*
C19	1.00905 (7)	0.19155 (10)	1.0914 (4)	0.0585 (5)
H19	1.0265	0.1758	0.9521	0.070*
C20	0.96386 (6)	0.25054 (10)	1.0421 (3)	0.0528 (5)
H20	0.9430	0.2592	1.1775	0.063*
C21	0.98457 (6)	0.33341 (10)	0.9582 (3)	0.0489 (4)
H21	1.0036	0.3227	0.8193	0.059*
C22	1.02418 (7)	0.36991 (10)	1.1231 (4)	0.0573 (5)
H22A	1.0386	0.4207	1.0623	0.069*
H22B	1.0061	0.3835	1.2607	0.069*
C23	1.06905 (7)	0.30999 (11)	1.1726 (4)	0.0644 (5)
H23A	1.0908	0.3029	1.0411	0.077*
H23B	1.0910	0.3319	1.2909	0.077*
C24	0.94118 (7)	0.39470 (10)	0.9057 (3)	0.0503 (5)
C25	0.94124 (8)	0.43858 (12)	0.7092 (4)	0.0663 (6)
H25	0.9676	0.4285	0.6051	0.080*
C26	0.90288 (10)	0.49765 (13)	0.6625 (4)	0.0772 (6)
H26	0.9039	0.5267	0.5290	0.093*
C27	0.86400 (9)	0.51280 (13)	0.8116 (4)	0.0760 (7)
H27	0.8384	0.5525	0.7815	0.091*
C28	0.86265 (8)	0.46921 (12)	1.0066 (4)	0.0744 (6)
H28	0.8358	0.4790	1.1089	0.089*
C29	0.90086 (7)	0.41091 (11)	1.0524 (4)	0.0645 (5)
H29	0.8993	0.3818	1.1858	0.077*
N1	0.70898 (6)	0.71810 (10)	0.3111 (3)	0.0613 (4)
N2	1.04696 (6)	0.23118 (9)	1.2390 (3)	0.0593 (4)
O1	0.66974 (6)	0.70369 (10)	−0.0274 (2)	0.0818 (4)
O2	0.82639 (5)	0.71371 (8)	0.6555 (2)	0.0659 (4)
H2	0.8562	0.7322	0.6361	0.099*
O3	1.07527 (5)	0.22642 (11)	1.5987 (3)	0.0834 (5)
O4	0.93197 (5)	0.21245 (8)	0.8770 (3)	0.0692 (4)
H4	0.9011	0.2126	0.9177	0.104*

	U11	U22	U33	U12	U13	U23
C2	0.0443 (10)	0.0671 (12)	0.0678 (13)	0.0000 (9)	0.0060 (11)	0.0075 (12)
C3	0.0637 (13)	0.0894 (15)	0.0783 (16)	0.0137 (12)	0.0105 (13)	−0.0048 (13)
C4	0.0652 (12)	0.0542 (11)	0.1030 (18)	0.0066 (10)	−0.0122 (13)	−0.0077 (13)
C5	0.0479 (10)	0.0502 (10)	0.0753 (13)	0.0015 (8)	−0.0063 (11)	0.0043 (10)
C6	0.0429 (9)	0.0494 (10)	0.0631 (11)	0.0036 (8)	−0.0035 (9)	0.0078 (9)
C7	0.0499 (10)	0.0588 (11)	0.0634 (12)	0.0020 (9)	0.0018 (10)	−0.0035 (10)
C8	0.0584 (11)	0.0573 (11)	0.0930 (16)	0.0153 (10)	−0.0111 (12)	−0.0116 (12)
C9	0.0505 (10)	0.0715 (13)	0.1002 (16)	0.0164 (10)	−0.0136 (12)	−0.0146 (13)
C10	0.0544 (11)	0.0565 (11)	0.0718 (14)	0.0025 (9)	0.0045 (11)	−0.0122 (12)
C11	0.0749 (14)	0.0838 (14)	0.0801 (16)	−0.0052 (13)	−0.0035 (14)	−0.0180 (14)
C12	0.0767 (16)	0.116 (2)	0.103 (2)	−0.0077 (16)	−0.0070 (16)	−0.044 (2)
C13	0.0757 (17)	0.0922 (19)	0.143 (3)	−0.0177 (15)	0.013 (2)	−0.055 (2)
C14	0.0886 (17)	0.0698 (15)	0.122 (2)	−0.0135 (13)	0.0244 (18)	−0.0141 (16)
C15	0.0773 (14)	0.0700 (13)	0.0849 (16)	−0.0060 (12)	0.0042 (13)	−0.0062 (13)
C16	0.0419 (10)	0.0744 (13)	0.0702 (14)	0.0068 (10)	−0.0016 (11)	−0.0008 (12)
C17	0.0671 (13)	0.0843 (15)	0.0992 (18)	−0.0090 (12)	−0.0081 (14)	0.0254 (15)
C18	0.1003 (16)	0.0486 (12)	0.113 (2)	−0.0054 (12)	−0.0228 (17)	0.0072 (13)
C19	0.0606 (11)	0.0459 (10)	0.0689 (12)	−0.0007 (9)	−0.0091 (11)	−0.0050 (10)
C20	0.0477 (9)	0.0468 (9)	0.0640 (12)	−0.0049 (8)	−0.0023 (10)	−0.0097 (9)
C21	0.0482 (9)	0.0446 (9)	0.0539 (10)	−0.0040 (8)	0.0039 (9)	−0.0045 (9)
C22	0.0554 (10)	0.0480 (10)	0.0686 (13)	−0.0098 (9)	−0.0035 (10)	−0.0005 (10)
C23	0.0546 (11)	0.0628 (12)	0.0757 (13)	−0.0126 (10)	−0.0113 (11)	0.0001 (11)
C24	0.0508 (10)	0.0432 (9)	0.0570 (12)	−0.0029 (8)	0.0003 (10)	−0.0059 (9)
C25	0.0712 (12)	0.0676 (12)	0.0600 (13)	0.0037 (11)	0.0034 (11)	0.0009 (11)
C26	0.0881 (15)	0.0690 (13)	0.0744 (15)	0.0075 (13)	−0.0120 (15)	0.0116 (12)
C27	0.0701 (14)	0.0567 (12)	0.1011 (18)	0.0137 (11)	−0.0146 (15)	−0.0048 (14)
C28	0.0708 (13)	0.0628 (12)	0.0896 (16)	0.0149 (11)	0.0144 (12)	−0.0013 (13)
C29	0.0669 (12)	0.0564 (11)	0.0702 (13)	0.0104 (10)	0.0101 (12)	0.0050 (11)
N1	0.0462 (8)	0.0581 (9)	0.0796 (12)	0.0064 (7)	−0.0119 (9)	−0.0075 (9)
N2	0.0567 (9)	0.0544 (9)	0.0668 (11)	−0.0036 (8)	−0.0117 (9)	0.0039 (9)
O1	0.0653 (8)	0.1100 (11)	0.0702 (9)	0.0164 (8)	−0.0082 (8)	0.0074 (9)
O2	0.0508 (6)	0.0617 (8)	0.0853 (9)	−0.0013 (6)	−0.0141 (8)	0.0166 (8)
O3	0.0571 (8)	0.1266 (13)	0.0666 (9)	−0.0098 (9)	−0.0081 (8)	0.0056 (10)
O4	0.0554 (7)	0.0635 (8)	0.0887 (10)	−0.0042 (7)	−0.0151 (8)	−0.0175 (8)

C2—O1	1.228 (2)	C16—N2	1.332 (3)
C2—N1	1.330 (3)	C16—C17	1.509 (3)
C2—C3	1.504 (3)	C17—C18	1.492 (3)
C3—C4	1.488 (3)	C17—H17A	0.9700
C3—H3A	0.9700	C17—H17B	0.9700
C3—H3B	0.9700	C18—C19	1.525 (3)
C4—C5	1.527 (3)	C18—H18A	0.9700
C4—H4A	0.9700	C18—H18B	0.9700
C4—H4B	0.9700	C19—N2	1.456 (2)
C5—N1	1.457 (2)	C19—C20	1.519 (2)
C5—C6	1.521 (2)	C19—H19	0.9800
C5—H5	0.9800	C20—O4	1.420 (2)
C6—O2	1.405 (2)	C20—C21	1.523 (2)
C6—C7	1.534 (2)	C20—H20	0.9800
C6—H6	0.9800	C21—C24	1.513 (2)
C7—C10	1.516 (3)	C21—C22	1.529 (2)
C7—C8	1.519 (3)	C21—H21	0.9800
C7—H7	0.9800	C22—C23	1.523 (2)
C8—C9	1.521 (3)	C22—H22A	0.9700
C8—H8A	0.9700	C22—H22B	0.9700
C8—H8B	0.9700	C23—N2	1.447 (2)
C9—N1	1.452 (2)	C23—H23A	0.9700
C9—H9A	0.9700	C23—H23B	0.9700
C9—H9B	0.9700	C24—C29	1.375 (2)
C10—C15	1.376 (3)	C24—C25	1.377 (3)
C10—C11	1.382 (3)	C25—C26	1.391 (3)
C11—C12	1.376 (3)	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.354 (3)
C12—C13	1.371 (4)	C26—H26	0.9300
C12—H12	0.9300	C27—C28	1.367 (3)
C13—C14	1.364 (4)	C27—H27	0.9300
C13—H13	0.9300	C28—C29	1.379 (3)
C14—C15	1.393 (3)	C28—H28	0.9300
C14—H14	0.9300	C29—H29	0.9300
C15—H15	0.9300	O2—H2	0.8200
C16—O3	1.229 (2)	O4—H4	0.8200
O1—C2—N1	125.73 (19)	C18—C17—H17A	110.6
O1—C2—C3	126.0 (2)	C16—C17—H17A	110.6
N1—C2—C3	108.22 (18)	C18—C17—H17B	110.6
C4—C3—C2	106.58 (18)	C16—C17—H17B	110.6
C4—C3—H3A	110.4	H17A—C17—H17B	108.8
C2—C3—H3A	110.4	C17—C18—C19	106.47 (18)
C4—C3—H3B	110.4	C17—C18—H18A	110.4
C2—C3—H3B	110.4	C19—C18—H18A	110.4
H3A—C3—H3B	108.6	C17—C18—H18B	110.4
C3—C4—C5	106.30 (16)	C19—C18—H18B	110.4
C3—C4—H4A	110.5	H18A—C18—H18B	108.6
C5—C4—H4A	110.5	N2—C19—C20	109.95 (14)
C3—C4—H4B	110.5	N2—C19—C18	103.20 (16)
C5—C4—H4B	110.5	C20—C19—C18	114.52 (17)
H4A—C4—H4B	108.7	N2—C19—H19	109.7
N1—C5—C6	110.71 (14)	C20—C19—H19	109.7
N1—C5—C4	103.92 (17)	C18—C19—H19	109.7
C6—C5—C4	114.52 (15)	O4—C20—C19	107.11 (14)
N1—C5—H5	109.2	O4—C20—C21	110.21 (16)
C6—C5—H5	109.2	C19—C20—C21	110.79 (13)
C4—C5—H5	109.2	O4—C20—H20	109.6
O2—C6—C5	105.47 (13)	C19—C20—H20	109.6
O2—C6—C7	112.52 (16)	C21—C20—H20	109.6
C5—C6—C7	111.74 (13)	C24—C21—C20	113.13 (13)
O2—C6—H6	109.0	C24—C21—C22	111.15 (13)
C5—C6—H6	109.0	C20—C21—C22	110.54 (15)
C7—C6—H6	109.0	C24—C21—H21	107.2
C10—C7—C8	113.73 (16)	C20—C21—H21	107.2
C10—C7—C6	110.46 (13)	C22—C21—H21	107.2
C8—C7—C6	110.69 (16)	C23—C22—C21	111.86 (15)
C10—C7—H7	107.2	C23—C22—H22A	109.2
C8—C7—H7	107.2	C21—C22—H22A	109.2
C6—C7—H7	107.2	C23—C22—H22B	109.2
C7—C8—C9	112.20 (16)	C21—C22—H22B	109.2
C7—C8—H8A	109.2	H22A—C22—H22B	107.9
C9—C8—H8A	109.2	N2—C23—C22	108.88 (14)
C7—C8—H8B	109.2	N2—C23—H23A	109.9
C9—C8—H8B	109.2	C22—C23—H23A	109.9
H8A—C8—H8B	107.9	N2—C23—H23B	109.9
N1—C9—C8	108.03 (14)	C22—C23—H23B	109.9
N1—C9—H9A	110.1	H23A—C23—H23B	108.3
C8—C9—H9A	110.1	C29—C24—C25	116.89 (17)
N1—C9—H9B	110.1	C29—C24—C21	122.11 (17)
C8—C9—H9B	110.1	C25—C24—C21	120.98 (17)
H9A—C9—H9B	108.4	C24—C25—C26	121.7 (2)
C15—C10—C11	117.3 (2)	C24—C25—H25	119.2
C15—C10—C7	122.0 (2)	C26—C25—H25	119.2
C11—C10—C7	120.6 (2)	C27—C26—C25	120.0 (2)
C12—C11—C10	121.6 (3)	C27—C26—H26	120.0
C12—C11—H11	119.2	C25—C26—H26	120.0
C10—C11—H11	119.2	C26—C27—C28	119.5 (2)
C13—C12—C11	120.3 (3)	C26—C27—H27	120.3
C13—C12—H12	119.9	C28—C27—H27	120.3
C11—C12—H12	119.9	C27—C28—C29	120.3 (2)
C14—C13—C12	119.5 (3)	C27—C28—H28	119.8
C14—C13—H13	120.2	C29—C28—H28	119.8
C12—C13—H13	120.2	C24—C29—C28	121.7 (2)
C13—C14—C15	120.0 (3)	C24—C29—H29	119.2
C13—C14—H14	120.0	C28—C29—H29	119.2
C15—C14—H14	120.0	C2—N1—C9	127.00 (18)
C10—C15—C14	121.3 (2)	C2—N1—C5	114.79 (16)
C10—C15—H15	119.3	C9—N1—C5	117.98 (17)
C14—C15—H15	119.3	C16—N2—C23	125.44 (17)
O3—C16—N2	125.70 (19)	C16—N2—C19	114.63 (16)
O3—C16—C17	126.0 (2)	C23—N2—C19	118.29 (16)
N2—C16—C17	108.29 (19)	C6—O2—H2	109.5
C18—C17—C16	105.60 (19)	C20—O4—H4	109.5
O1—C2—C3—C4	−177.3 (2)	C19—C20—C21—C24	179.82 (15)
N1—C2—C3—C4	2.8 (2)	O4—C20—C21—C22	−173.17 (13)
C2—C3—C4—C5	−4.3 (2)	C19—C20—C21—C22	−54.8 (2)
C3—C4—C5—N1	4.1 (2)	C24—C21—C22—C23	−178.28 (16)
C3—C4—C5—C6	−116.75 (18)	C20—C21—C22—C23	55.2 (2)
N1—C5—C6—O2	171.79 (16)	C21—C22—C23—N2	−52.5 (2)
C4—C5—C6—O2	−71.1 (2)	C20—C21—C24—C29	49.1 (2)
N1—C5—C6—C7	49.2 (2)	C22—C21—C24—C29	−75.9 (2)
C4—C5—C6—C7	166.31 (17)	C20—C21—C24—C25	−132.62 (18)
O2—C6—C7—C10	63.1 (2)	C22—C21—C24—C25	102.3 (2)
C5—C6—C7—C10	−178.45 (17)	C29—C24—C25—C26	1.1 (3)
O2—C6—C7—C8	−170.01 (15)	C21—C24—C25—C26	−177.25 (17)
C5—C6—C7—C8	−51.6 (2)	C24—C25—C26—C27	−0.5 (3)
C10—C7—C8—C9	−179.74 (18)	C25—C26—C27—C28	−0.5 (3)
C6—C7—C8—C9	55.2 (2)	C26—C27—C28—C29	0.7 (3)
C7—C8—C9—N1	−55.0 (3)	C25—C24—C29—C28	−0.9 (3)
C8—C7—C10—C15	−35.5 (3)	C21—C24—C29—C28	177.43 (18)
C6—C7—C10—C15	89.6 (2)	C27—C28—C29—C24	0.0 (3)
C8—C7—C10—C11	146.7 (2)	O1—C2—N1—C9	−5.6 (3)
C6—C7—C10—C11	−88.1 (2)	C3—C2—N1—C9	174.26 (18)
C15—C10—C11—C12	−0.1 (3)	O1—C2—N1—C5	−179.96 (18)
C7—C10—C11—C12	177.7 (2)	C3—C2—N1—C5	−0.1 (2)
C10—C11—C12—C13	0.3 (3)	C8—C9—N1—C2	−118.1 (2)
C11—C12—C13—C14	0.2 (4)	C8—C9—N1—C5	56.0 (2)
C12—C13—C14—C15	−0.8 (4)	C6—C5—N1—C2	120.80 (18)
C11—C10—C15—C14	−0.5 (3)	C4—C5—N1—C2	−2.6 (2)
C7—C10—C15—C14	−178.30 (18)	C6—C5—N1—C9	−54.1 (2)
C13—C14—C15—C10	1.0 (3)	C4—C5—N1—C9	−177.47 (16)
O3—C16—C17—C18	−176.3 (2)	O3—C16—N2—C23	−9.5 (3)
N2—C16—C17—C18	4.6 (2)	C17—C16—N2—C23	169.56 (17)
C16—C17—C18—C19	−11.2 (2)	O3—C16—N2—C19	−174.60 (17)
C17—C18—C19—N2	13.4 (2)	C17—C16—N2—C19	4.5 (2)
C17—C18—C19—C20	−106.1 (2)	C22—C23—N2—C16	−110.3 (2)
N2—C19—C20—O4	172.89 (15)	C22—C23—N2—C19	54.3 (2)
C18—C19—C20—O4	−71.5 (2)	C20—C19—N2—C16	111.25 (18)
N2—C19—C20—C21	52.6 (2)	C18—C19—N2—C16	−11.3 (2)
C18—C19—C20—C21	168.28 (16)	C20—C19—N2—C23	−55.0 (2)
O4—C20—C21—C24	61.46 (19)	C18—C19—N2—C23	−177.57 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1i	0.82	1.92	2.7366 (19)	175
O2—H2···O3ii	0.82	1.88	2.6963 (18)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1i	0.82	1.92	2.7366 (19)	175
O2—H2⋯O3ii	0.82	1.88	2.6963 (18)	179

Symmetry codes: (i) ; (ii) .