Mersinine A from Kopsia fruticosa

The pentacyclic quinoline alkaloid mersinine A, C₂₅H₂₈N₂O₉, was isolated from the leaves of Kopsia fruticosa (Ker.) A DC. The mol­ecule has a hydroxyl group that forms a hydrogen bond with the carbonyl O atom of an adjacent mol­ecule, which gives rise to infinite chains running along the c axis of the crystal.

Key indicators

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.084
• Data-to-parameter ratio = 7.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.50
         From the CIF: _reflns_number_total               2493
         Count of symmetry unique reflns         2547
         Completeness (_total/calc)             97.88%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

Mersinines A and B, and mersiloscine are pentacyclic quinolinic alkaloids that are found within the genus Kopsia. These alkaloids contain a meloscine skeleton whose five-membered C ring has an additional C atom. The title alkaloid, mersinine A, (I), isolated from the leaves of Kopsia fruticosa (Ker.) A. DC., possesses a tetrahydroquinoline chromophore and its structure has been determined by solution NMR spectroscopy (Kam et al., 2001). The present study reports the solid-state structure, which confirms the NMR results (Fig. 1). The hydroxyl group forms a hydrogen bond to the carbonyl O atom of an adjacent carboxyl unit [O9···O6ⁱ 2.873 (2) Å and O9—H9o···O6ⁱ 133 (3)°; symmetry code: (i) x, y, z − 1], thus giving rise to linear chains running along the c axis of the crystal.

S2. Experimental

The title alkaloid was isolated from the leaves of Kopsia fruticosa (Ker.) A. DC. (Kam et al., 2001), and crystals were grown from its ether solution.

S3. Refinement

Refinement of the Flack parameter (Flack & Schwarzenbach, 1988) was suppressed by the MERG 4 command in SHELXL97 (Sheldrick, 1997) as the lack of anomalous scatterers did not allow for the absolute configuration to be determined from the X-ray measurements. The absolute configuration was taken as reported in the solution NMR study of the compound (Kam et al., 2001). That study had assumed the configuration to be that of a structurally related compound, meloscine (Bernauer et al., 1969), whose absolute configuration was determined from the X-ray structure of the brominated derivative (Oberha¨nsli, 1969). The C-bound H atoms were positioned geometrically, and were allowed to ride on their parent atoms [U_iso(H) = 1.2U_eq(C) for the aromatic, methylene and methine C atoms, and 1.5U_eq(C) for the methyl C atoms]. The hydroxyl H atom was located and refined [O9—H1o = 0.80 (4) Å].

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEPII (Johnson, 1976) plot of (I), with ellipsoids at the 50% probability level. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. ORTEPII (Johnson, 1976) plot showing the infinite chains of molecules linked by O—H···O bonds.

(5R,5aR,7aR,11aR,13aR)-5,5a,6,7,12,13-Hexahydro-5-hydroxy-4H,10H-1,3,- benzodioxolo[4,5-κ]pyrrolo[3,2,1-mn][1,8]phenanthroline-4,5,7a(10aH)- tricarboxylic acid trimethyl ester

Crystal data

C25H28N2O9	F(000) = 1056
Mr = 500.49	Dx = 1.450 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 29.005 (2) Å	Cell parameters from 5856 reflections
b = 8.5430 (6) Å	θ = 2.2–26.5°
c = 9.3081 (7) Å	µ = 0.11 mm^−1
β = 96.163 (1)°	T = 168 K
V = 2293.1 (3) Å^3	Plate, colorless
Z = 4	0.50 × 0.16 × 0.14 mm

Data collection

Bruker AXS CCD area-detector diffractometer	2173 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 26.5°, θmin = 2.2°
ω scans	h = −35→36
15060 measured reflections	k = −10→5
2493 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.061P)^2] where P = (Fo^2 + 2Fc^2)/3
2493 reflections	(Δ/σ)max = 0.001
329 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1925 (1)	0.5001 (2)	0.1924 (2)	0.030 (1)
O2	0.2132 (1)	0.7325 (2)	0.1080 (2)	0.033 (1)
O3	0.2199 (1)	0.8567 (3)	0.4023 (2)	0.037 (1)
O4	0.2141 (1)	1.0595 (3)	0.2515 (3)	0.054 (1)
O5	0.1349 (1)	1.2190 (2)	0.7433 (2)	0.035 (1)
O6	0.1472 (1)	0.9758 (2)	0.8187 (2)	0.032 (1)
O7	0.1051 (1)	0.4502 (3)	0.0505 (2)	0.041 (1)
O8	0.0415 (1)	0.3113 (3)	0.1143 (2)	0.046 (1)
O9	0.1320 (1)	0.9547 (2)	0.1180 (2)	0.039 (1)
N1	0.1503 (1)	0.7125 (3)	0.2319 (2)	0.024 (1)
N2	0.0793 (1)	0.7490 (3)	0.6923 (2)	0.028 (1)
C1	0.2323 (1)	0.4322 (4)	0.1339 (3)	0.035 (1)
C2	0.1876 (1)	0.6517 (3)	0.1697 (2)	0.025 (1)
C3	0.1493 (1)	0.8818 (3)	0.2467 (2)	0.027 (1)
C4	0.1984 (1)	0.9437 (3)	0.2959 (3)	0.035 (1)
C5	0.2644 (1)	0.9136 (5)	0.4666 (4)	0.056 (1)
C6	0.1156 (1)	0.9272 (3)	0.3580 (2)	0.024 (1)
C7	0.1096 (1)	0.8009 (3)	0.4738 (2)	0.022 (1)
C8	0.0894 (1)	0.6634 (3)	0.3871 (2)	0.023 (1)
C9	0.1112 (1)	0.6233 (3)	0.2640 (2)	0.023 (1)
C10	0.0917 (1)	0.5058 (3)	0.1777 (2)	0.026 (1)
C11	0.0723 (1)	0.3299 (4)	0.0061 (3)	0.050 (1)
C12	0.0533 (1)	0.4262 (3)	0.2140 (3)	0.029 (1)
C13	0.0315 (1)	0.4608 (3)	0.3326 (3)	0.029 (1)
C14	0.0506 (1)	0.5817 (3)	0.4190 (2)	0.028 (1)
C15	0.1501 (1)	0.7419 (3)	0.5824 (2)	0.024 (1)
C16	0.1245 (1)	0.6718 (3)	0.7036 (3)	0.030 (1)
C17	0.0565 (1)	0.7866 (4)	0.8212 (3)	0.038 (1)
C18	0.0328 (1)	0.9398 (4)	0.8112 (3)	0.040 (1)
C19	0.0435 (1)	1.0548 (4)	0.7264 (3)	0.035 (1)
C20	0.0828 (1)	1.0328 (3)	0.6324 (3)	0.027 (1)
C21	0.0762 (1)	0.8625 (3)	0.5783 (2)	0.024 (1)
C22	0.1258 (1)	1.0671 (3)	0.7389 (2)	0.026 (1)
C23	0.1721 (1)	1.2677 (3)	0.8502 (3)	0.038 (1)
C24	0.0823 (1)	1.1384 (3)	0.5005 (3)	0.032 (1)
C25	0.1224 (1)	1.0928 (3)	0.4151 (3)	0.031 (1)
H1o	0.150 (1)	0.944 (5)	0.061 (4)	0.06 (1)*
H1a	0.2336	0.3198	0.1549	0.052*
H1b	0.2607	0.4827	0.1783	0.052*
H1c	0.2295	0.4484	0.0291	0.052*
H5a	0.2768	0.8418	0.5432	0.084*
H5b	0.2605	1.0178	0.5077	0.084*
H5c	0.2859	0.9198	0.3925	0.084*
H6	0.0846	0.9307	0.2995	0.029*
H11a	0.0546	0.3588	−0.0870	0.060*
H11b	0.0887	0.2302	−0.0074	0.060*
H13	0.0047	0.4055	0.3547	0.035*
H14	0.0366	0.6092	0.5032	0.033*
H15a	0.1687	0.6615	0.5382	0.029*
H15b	0.1706	0.8291	0.6186	0.029*
H16a	0.1207	0.5573	0.6908	0.036*
H16b	0.1418	0.6923	0.7992	0.036*
H17a	0.0800	0.7866	0.9066	0.046*
H17b	0.0335	0.7039	0.8357	0.046*
H18	0.0083	0.9565	0.8696	0.048*
H19	0.0268	1.1506	0.7241	0.042*
H21	0.0442	0.8549	0.5270	0.029*
H23a	0.1761	1.3814	0.8448	0.057*
H23b	0.2010	1.2156	0.8313	0.057*
H23c	0.1645	1.2391	0.9468	0.057*
H24a	0.0856	1.2491	0.5314	0.038*
H24b	0.0525	1.1270	0.4389	0.038*
H25a	0.1239	1.1662	0.3335	0.037*
H25b	0.1520	1.0998	0.4783	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.026 (1)	0.030 (1)	0.033 (1)	−0.001 (1)	0.005 (1)	−0.005 (1)
O2	0.029 (1)	0.039 (1)	0.033 (1)	−0.004 (1)	0.012 (1)	−0.002 (1)
O3	0.032 (1)	0.051 (1)	0.028 (1)	−0.018 (1)	0.002 (1)	−0.006 (1)
O4	0.065 (1)	0.037 (1)	0.065 (1)	−0.021 (1)	0.025 (1)	−0.002 (1)
O5	0.035 (1)	0.031 (1)	0.036 (1)	0.002 (1)	−0.008 (1)	−0.008 (1)
O6	0.034 (1)	0.038 (1)	0.024 (1)	0.001 (1)	−0.005 (1)	−0.001 (1)
O7	0.033 (1)	0.057 (1)	0.034 (1)	−0.012 (1)	0.010 (1)	−0.026 (1)
O8	0.040 (1)	0.048 (1)	0.051 (1)	−0.016 (1)	0.012 (1)	−0.028 (1)
O9	0.060 (1)	0.039 (1)	0.020 (1)	0.006 (1)	0.008 (1)	0.006 (1)
N1	0.026 (1)	0.026 (1)	0.022 (1)	−0.003 (1)	0.005 (1)	−0.006 (1)
N2	0.029 (1)	0.037 (1)	0.020 (1)	−0.001 (1)	0.006 (1)	−0.002 (1)
C1	0.024 (1)	0.038 (2)	0.043 (1)	0.002 (1)	0.004 (1)	−0.009 (1)
C2	0.024 (1)	0.034 (1)	0.019 (1)	−0.004 (1)	0.002 (1)	−0.004 (1)
C3	0.037 (1)	0.027 (1)	0.018 (1)	−0.002 (1)	0.004 (1)	−0.001 (1)
C4	0.043 (2)	0.031 (1)	0.034 (1)	−0.010 (1)	0.017 (1)	−0.010 (1)
C5	0.035 (2)	0.081 (3)	0.053 (2)	−0.022 (2)	0.003 (1)	−0.024 (2)
C6	0.030 (1)	0.024 (1)	0.018 (1)	0.002 (1)	0.000 (1)	−0.001 (1)
C7	0.022 (1)	0.025 (1)	0.018 (1)	0.001 (1)	0.003 (1)	−0.003 (1)
C8	0.024 (1)	0.024 (1)	0.022 (1)	0.004 (1)	0.001 (1)	−0.001 (1)
C9	0.023 (1)	0.025 (1)	0.020 (1)	0.001 (1)	0.001 (1)	−0.001 (1)
C10	0.023 (1)	0.033 (1)	0.023 (1)	0.004 (1)	0.005 (1)	−0.005 (1)
C11	0.045 (2)	0.058 (2)	0.048 (2)	−0.016 (2)	0.012 (1)	−0.031 (2)
C12	0.028 (1)	0.027 (1)	0.030 (1)	−0.002 (1)	−0.001 (1)	−0.009 (1)
C13	0.024 (1)	0.032 (1)	0.034 (1)	−0.004 (1)	0.007 (1)	−0.003 (1)
C14	0.028 (1)	0.032 (1)	0.024 (1)	0.000 (1)	0.007 (1)	−0.004 (1)
C15	0.025 (1)	0.026 (1)	0.021 (1)	0.002 (1)	0.001 (1)	−0.001 (1)
C16	0.035 (1)	0.032 (2)	0.023 (1)	−0.001 (1)	0.001 (1)	0.001 (1)
C17	0.040 (2)	0.053 (2)	0.024 (1)	−0.011 (1)	0.010 (1)	−0.009 (1)
C18	0.030 (1)	0.061 (2)	0.031 (1)	−0.002 (1)	0.008 (1)	−0.018 (1)
C19	0.026 (1)	0.045 (2)	0.033 (1)	0.005 (1)	−0.002 (1)	−0.020 (1)
C20	0.028 (1)	0.032 (2)	0.021 (1)	0.006 (1)	−0.001 (1)	−0.007 (1)
C21	0.022 (1)	0.033 (1)	0.019 (1)	0.001 (1)	0.002 (1)	−0.006 (1)
C22	0.025 (1)	0.033 (1)	0.020 (1)	0.004 (1)	0.005 (1)	−0.006 (1)
C23	0.031 (1)	0.037 (2)	0.043 (1)	−0.002 (1)	−0.008 (1)	−0.011 (1)
C24	0.041 (1)	0.027 (1)	0.026 (1)	0.010 (1)	−0.008 (1)	−0.006 (1)
C25	0.045 (2)	0.024 (1)	0.023 (1)	0.000 (1)	−0.001 (1)	−0.002 (1)

Geometric parameters (Å, º)

O1—C1	1.449 (3)	C18—C19	1.319 (4)
O1—C2	1.317 (3)	C19—C20	1.520 (3)
O2—C2	1.206 (3)	C20—C21	1.545 (3)
O3—C4	1.337 (4)	C20—C22	1.536 (3)
O3—C5	1.447 (3)	C20—C24	1.523 (4)
O4—C4	1.182 (3)	C24—C25	1.526 (4)
O5—C22	1.325 (4)	O9—H1o	0.80 (4)
O5—C23	1.448 (3)	C1—H1a	0.98
O6—C22	1.202 (3)	C1—H1b	0.98
O7—C10	1.370 (3)	C1—H1c	0.98
O7—C11	1.432 (3)	C5—H5a	0.98
O8—C11	1.425 (3)	C5—H5b	0.98
O8—C12	1.369 (3)	C5—H5c	0.98
O9—C3	1.396 (3)	C6—H6	1
N1—C2	1.381 (3)	C11—H11a	0.99
N1—C3	1.453 (3)	C11—H11b	0.99
N1—C9	1.423 (3)	C13—H13	0.95
N2—C16	1.459 (3)	C14—H14	0.95
N2—C17	1.467 (3)	C15—H15a	0.99
N2—C21	1.433 (3)	C15—H15b	0.99
C3—C4	1.541 (4)	C16—H16a	0.99
C3—C6	1.549 (3)	C16—H16b	0.99
C6—C7	1.548 (3)	C17—H17a	0.99
C7—C8	1.508 (3)	C17—H17b	0.99
C6—C25	1.517 (3)	C18—H18	0.95
C7—C15	1.549 (3)	C19—H19	0.95
C7—C21	1.537 (3)	C21—H21	1
C8—C9	1.410 (3)	C23—H23a	0.98
C8—C14	1.382 (3)	C23—H23b	0.98
C9—C10	1.370 (3)	C23—H23c	0.98
C10—C12	1.377 (4)	C24—H24a	0.99
C12—C13	1.362 (3)	C24—H24b	0.99
C13—C14	1.388 (4)	C25—H25a	0.99
C15—C16	1.537 (3)	C25—H25b	0.99
C17—C18	1.476 (4)
C1—O1—C2	114.2 (2)	C6—C25—C24	110.1 (2)
C4—O3—C5	116.3 (2)	C3—O9—H1o	108 (3)
C22—O5—C23	115.8 (2)	O1—C1—H1a	109.5
C10—O7—C11	104.8 (2)	O1—C1—H1b	109.5
C11—O8—C12	105.6 (2)	H1a—C1—H1b	109.5
C2—N1—C3	116.0 (2)	O1—C1—H1C	109.5
C2—N1—C9	124.2 (2)	H1a—C1—H1C	109.5
C3—N1—C9	119.3 (2)	H1b—C1—H1C	109.5
C16—N2—C17	121.3 (2)	O3—C5—H5a	109.5
C16—N2—C21	110.1 (2)	O3—C5—H5b	109.5
C17—N2—C21	117.4 (2)	H5a—C5—H5b	109.5
O1—C2—O2	125.2 (2)	O3—C5—H5C	109.5
O1—C2—N1	112.3 (2)	H5a—C5—H5C	109.5
O2—C2—N1	122.4 (2)	H5b—C5—H5C	109.5
O9—C3—N1	111.8 (2)	C25—C6—H6	103.8
O9—C3—C4	109.8 (2)	C7—C6—H6	103.8
O9—C3—C6	105.5 (2)	C3—C6—H6	103.8
N1—C3—C4	110.1 (2)	O8—C11—H11a	109.9
N1—C3—C6	109.4 (2)	O7—C11—H11a	109.9
C4—C3—C6	110.2 (2)	O8—C11—H11b	109.9
O3—C4—O4	123.9 (3)	O7—C11—H11b	109.9
O3—C4—C3	111.8 (2)	H11a—C11—H11b	108.3
O4—C4—C3	124.1 (3)	C12—C13—H13	122.0
C3—C6—C25	113.6 (2)	C14—C13—H13	122.0
C7—C6—C25	115.2 (2)	C8—C14—H14	118.8
C3—C6—C7	114.7 (2)	C13—C14—H14	118.8
C6—C7—C8	103.7 (2)	C16—C15—H15a	111.3
C6—C7—C21	109.1 (2)	C7—C15—H15a	111.3
C8—C7—C15	108.6 (2)	C16—C15—H15b	111.3
C8—C7—C21	111.7 (2)	C7—C15—H15b	111.3
C6—C7—C15	123.2 (2)	H15a—C15—H15b	109.2
C15—C7—C21	100.6 (2)	N2—C16—H16a	110.6
C7—C8—C9	116.2 (2)	C15—C16—H16a	110.6
C7—C8—C14	123.8 (2)	N2—C16—H16b	110.6
C9—C8—C14	119.9 (2)	C15—C16—H16b	110.6
C8—C9—C10	117.4 (2)	H16a—C16—H16b	108.7
C8—C9—N1	118.6 (2)	N2—C17—H17a	109.0
C10—C9—N1	123.9 (2)	C18—C17—H17a	109.0
O7—C10—C9	128.5 (2)	N2—C17—H17b	109.0
O7—C10—C12	110.7 (2)	C18—C17—H17b	109.0
C9—C10—C12	120.8 (2)	H17a—C17—H17b	107.8
O7—C11—O8	108.9 (2)	C19—C18—H18	118.0
C13—C12—O8	126.9 (2)	C17—C18—H18	118.0
C10—C12—C13	123.4 (2)	C18—C19—H19	120.3
O8—C12—C10	109.7 (2)	C20—C19—H19	120.3
C12—C13—C14	116.0 (2)	N2—C21—H21	107.0
C8—C14—C13	122.4 (2)	C7—C21—H21	107.0
C7—C15—C16	102.4 (2)	C20—C21—H21	107.0
N2—C16—C15	105.7 (2)	O5—C23—H23a	109.5
N2—C17—C18	113.0 (2)	O5—C23—H23b	109.5
C17—C18—C19	124.1 (2)	H23a—C23—H23b	109.5
C18—C19—C20	119.5 (3)	O5—C23—H23C	109.5
C19—C20—C22	102.2 (2)	H23a—C23—H23C	109.5
C19—C20—C24	116.7 (2)	H23b—C23—H23C	109.5
C19—C20—C21	103.3 (2)	C20—C24—H24a	109.9
C21—C20—C22	117.0 (2)	C25—C24—H24a	109.9
C21—C20—C24	107.8 (2)	C20—C24—H24b	109.9
C22—C20—C24	110.1 (2)	C25—C24—H24b	109.9
N2—C21—C7	104.1 (2)	H24a—C24—H24b	108.3
N2—C21—C20	113.6 (2)	C6—C25—H25a	109.6
C7—C21—C20	117.7 (2)	C24—C25—H25a	109.6
O5—C22—O6	121.9 (2)	C6—C25—H25b	109.6
O5—C22—C20	110.7 (2)	C24—C25—H25b	109.6
O6—C22—C20	127.2 (2)	H25a—C25—H25b	108.2
C20—C24—C25	109.1 (2)
C1—O1—C2—O2	−0.8 (3)	C11—O8—C12—C13	175.6 (3)
C1—O1—C2—N1	−177.7 (2)	C11—O8—C12—C10	−4.4 (3)
C9—N1—C2—O2	159.0 (2)	O7—C10—C12—C13	−177.6 (2)
C3—N1—C2—O2	−12.9 (3)	C9—C10—C12—C13	2.3 (4)
C9—N1—C2—O1	−24.1 (3)	O7—C10—C12—O8	2.5 (3)
C3—N1—C2—O1	164.1 (2)	C9—C10—C12—O8	−177.7 (2)
C2—N1—C3—O9	81.2 (3)	O8—C12—C13—C14	178.9 (2)
C9—N1—C3—O9	−91.1 (2)	C10—C12—C13—C14	−1.0 (4)
C2—N1—C3—C4	−41.1 (3)	C9—C8—C14—C13	−0.9 (4)
C9—N1—C3—C4	146.6 (2)	C7—C8—C14—C13	176.5 (2)
C2—N1—C3—C6	−162.3 (2)	C12—C13—C14—C8	0.4 (4)
C9—N1—C3—C6	25.4 (3)	C8—C7—C15—C16	−79.5 (2)
C5—O3—C4—O4	1.6 (4)	C21—C7—C15—C16	37.9 (2)
C5—O3—C4—C3	−174.0 (2)	C6—C7—C15—C16	159.3 (2)
O9—C3—C4—O4	16.5 (4)	C21—N2—C16—C15	−1.9 (3)
N1—C3—C4—O4	140.0 (3)	C17—N2—C16—C15	−144.6 (2)
C6—C3—C4—O4	−99.3 (3)	C7—C15—C16—N2	−23.3 (2)
O9—C3—C4—O3	−168.0 (2)	C21—N2—C17—C18	0.6 (3)
N1—C3—C4—O3	−44.5 (3)	C16—N2—C17—C18	140.8 (2)
C6—C3—C4—O3	76.3 (3)	N2—C17—C18—C19	−23.1 (4)
O9—C3—C6—C25	−76.8 (2)	C17—C18—C19—C20	−0.5 (4)
N1—C3—C6—C25	162.8 (2)	C18—C19—C20—C24	158.1 (2)
C4—C3—C6—C25	41.6 (3)	C18—C19—C20—C22	−81.8 (3)
O9—C3—C6—C7	147.7 (2)	C18—C19—C20—C21	40.0 (3)
N1—C3—C6—C7	27.3 (3)	C16—N2—C21—C7	26.7 (2)
C4—C3—C6—C7	−93.9 (3)	C17—N2—C21—C7	171.1 (2)
C25—C6—C7—C8	163.3 (2)	C16—N2—C21—C20	−102.5 (2)
C3—C6—C7—C8	−61.9 (2)	C17—N2—C21—C20	41.9 (3)
C25—C6—C7—C21	44.1 (3)	C8—C7—C21—N2	75.2 (2)
C3—C6—C7—C21	178.9 (2)	C6—C7—C21—N2	−170.7 (2)
C25—C6—C7—C15	−73.2 (3)	C15—C7—C21—N2	−39.9 (2)
C3—C6—C7—C15	61.6 (3)	C8—C7—C21—C20	−158.2 (2)
C21—C7—C8—C14	−13.1 (3)	C6—C7—C21—C20	−44.1 (2)
C6—C7—C8—C14	−130.6 (2)	C15—C7—C21—C20	86.7 (2)
C15—C7—C8—C14	96.9 (3)	C19—C20—C21—N2	−60.2 (2)
C21—C7—C8—C9	164.3 (2)	C24—C20—C21—N2	175.7 (2)
C6—C7—C8—C9	46.9 (2)	C22—C20—C21—N2	51.1 (3)
C15—C7—C8—C9	−85.6 (2)	C19—C20—C21—C7	177.9 (2)
C14—C8—C9—C10	2.0 (3)	C24—C20—C21—C7	53.8 (3)
C7—C8—C9—C10	−175.6 (2)	C22—C20—C21—C7	−70.7 (3)
C14—C8—C9—N1	178.3 (2)	C23—O5—C22—O6	−0.1 (3)
C7—C8—C9—N1	0.7 (3)	C23—O5—C22—C20	174.3 (2)
C2—N1—C9—C10	−37.8 (3)	C19—C20—C22—O6	87.4 (3)
C3—N1—C9—C10	133.8 (2)	C24—C20—C22—O6	−148.0 (2)
C2—N1—C9—C8	146.2 (2)	C21—C20—C22—O6	−24.6 (3)
C3—N1—C9—C8	−42.2 (3)	C19—C20—C22—O5	−86.6 (2)
C11—O7—C10—C9	−179.2 (3)	C24—C20—C22—O5	38.0 (3)
C11—O7—C10—C12	0.6 (3)	C21—C20—C22—O5	161.4 (2)
C8—C9—C10—O7	177.2 (2)	C19—C20—C24—C25	−176.6 (2)
N1—C9—C10—O7	1.1 (4)	C22—C20—C24—C25	67.6 (3)
C8—C9—C10—C12	−2.6 (3)	C21—C20—C24—C25	−61.0 (2)
N1—C9—C10—C12	−178.7 (2)	C7—C6—C25—C24	−55.6 (3)
C12—O8—C11—O7	4.8 (3)	C3—C6—C25—C24	169.1 (2)
C10—O7—C11—O8	−3.4 (3)	C20—C24—C25—C6	63.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H1o···O6^i	0.80 (4)	2.26 (4)	2.873 (2)	133 (3)

Symmetry code: (i) x, y, z−1.