14-Benzoyl-mesaconine hydro-chloride methanol monosolvate.

The title compound, C(31)H(44)N(3)O(10) (+)·Cl(-)·CH(4)O, is the methanol solvate of 8-benzo-yloxy-,9,11,11a-tetra-hydroxy-6,10,13-trimeth-oxy-3-meth-oxy-methyl-1-methyl-tetra-deca-hydro-1H-3,6a,12-(epiethane-1,1,2-tri-yl)-7,9-methanona-phtho[2,3-b]azocin-1-ium chloride, the amine-protonated hydro-chloride of 14-benzoyl-mesaconine hydro-chloride. The cation has an aconitine carbon skeleton with four six-membered rings of which three display chair conformations and one a boat conformation, and two five-membered rings with envelope conformations. In the crystal, the components are connected into an infinite chain by inter- and intra-molecular O-H⋯O, N-H⋯O and O-H⋯Cl hydrogen bonds.

Related literature

For general background to diterpenoid alkaloids, see: Ameri (1998 ▶); Desai et al. (1998 ▶); Suzuki et al. (1994 ▶). For the chemical structure of the title compound established from MS data, see: Zhang et al. (2005 ▶); Wang et al. (2009 ▶); Yue et al. (2009 ▶). For background to the strong toxicity of Aconitum alkaloids, see: Zhang et al. (2002 ▶). For ring numbering and ring conformations of the title compound, see: He et al. (2008 ▶).

Experimental

Crystal data

C31H44NO10 +·Cl−·CH4O

M = 658.16

Orthorhombic,

a = 12.919 (3) Å

b = 15.748 (3) Å

c = 16.045 (3) Å

V = 3264.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 123 K

0.30 × 0.20 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.969, T max = 0.977

29100 measured reflections

6908 independent reflections

4585 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.151

S = 1.10

6908 reflections

422 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.50 e Å−3

Absolute structure: Flack (1983 ▶), 1726 Friedel pairs

Flack parameter: −0.01 (11)

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010300/zl2352sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010300/zl2352Isup2.hkl

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

C31H44NO10+·Cl−·CH4O	F(000) = 1408
Mr = 658.16	Dx = 1.339 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5837 reflections
a = 12.919 (3) Å	θ = 2.8–27.9°
b = 15.748 (3) Å	µ = 0.18 mm−1
c = 16.045 (3) Å	T = 123 K
V = 3264.2 (11) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Rigaku/MSC Mercury CCD diffractometer	6908 independent reflections
Radiation source: fine-focus sealed tube	4585 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 26.8°, θmin = 3.0°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −16→16
Tmin = 0.969, Tmax = 0.977	k = −19→19
29100 measured reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.040P)2 + 3.5P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.151	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.36 e Å−3
6908 reflections	Δρmin = −0.50 e Å−3
422 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0187 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1726 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (11)

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	0.2155 (3)	0.3580 (2)	0.1441 (2)	0.0676 (9)
O2	0.2226 (2)	0.37571 (18)	0.28249 (16)	0.0457 (7)
O3	0.2193 (2)	0.53973 (19)	0.3747 (2)	0.0562 (8)
H3A	0.1791	0.5138	0.4050	0.084*
O4	0.4338 (2)	0.30793 (17)	0.47185 (17)	0.0462 (7)
H4A	0.4359	0.2560	0.4693	0.069*
O5	0.2329 (2)	0.40600 (19)	0.47032 (18)	0.0525 (7)
O6	0.4216 (2)	0.26331 (16)	0.27517 (17)	0.0448 (7)
H6	0.4352	0.2220	0.3044	0.067*
O7	0.6872 (2)	0.28611 (17)	0.23706 (19)	0.0500 (7)
O8	0.6159 (2)	0.59029 (17)	0.42349 (19)	0.0523 (7)
O9	0.8284 (2)	0.5542 (2)	0.4047 (2)	0.0591 (8)
H9	0.8901	0.5451	0.4126	0.089*
O10	0.8654 (2)	0.4637 (2)	0.1640 (2)	0.0633 (9)
N1	0.6874 (2)	0.4220 (2)	0.4292 (2)	0.0434 (8)
H1	0.696 (4)	0.4762 (16)	0.446 (3)	0.076 (17)*
C1	0.0994 (3)	0.2805 (2)	0.2312 (2)	0.0414 (9)
C2	0.0520 (3)	0.2385 (3)	0.1659 (3)	0.0452 (9)
H2	0.0758	0.2469	0.1118	0.054*
C3	−0.0302 (3)	0.1842 (3)	0.1797 (3)	0.0560 (11)
H3	−0.0619	0.1566	0.1353	0.067*
C4	−0.0649 (4)	0.1712 (3)	0.2602 (3)	0.0586 (11)
H4	−0.1205	0.1349	0.2699	0.070*
C5	−0.0174 (4)	0.2119 (3)	0.3265 (3)	0.0595 (12)
H5	−0.0404	0.2027	0.3807	0.071*
C6	0.0649 (3)	0.2668 (3)	0.3116 (3)	0.0517 (10)
H6A	0.0968	0.2943	0.3559	0.062*
C7	0.1852 (3)	0.3401 (3)	0.2127 (3)	0.0450 (9)
C8	0.2993 (3)	0.4412 (3)	0.2759 (2)	0.0410 (9)
H8	0.2795	0.4810	0.2317	0.049*
C9	0.4112 (3)	0.4122 (2)	0.2622 (2)	0.0394 (8)
H9A	0.4209	0.3946	0.2042	0.047*
C10	0.4718 (3)	0.4964 (2)	0.2794 (3)	0.0410 (9)
H10	0.4736	0.5284	0.2270	0.049*
C11	0.3996 (3)	0.5450 (2)	0.3401 (3)	0.0468 (10)
H11A	0.4360	0.5578	0.3915	0.056*
H11B	0.3771	0.5980	0.3152	0.056*
C12	0.3068 (3)	0.4881 (2)	0.3577 (3)	0.0423 (9)
C13	0.3285 (3)	0.4250 (2)	0.4295 (3)	0.0424 (9)
H13	0.3749	0.4523	0.4697	0.051*
C14	0.3773 (3)	0.3403 (2)	0.4020 (2)	0.0380 (8)
H14	0.3197	0.3009	0.3927	0.046*
C15	0.4424 (3)	0.3400 (2)	0.3210 (2)	0.0380 (8)
C16	0.5854 (3)	0.4909 (2)	0.3125 (2)	0.0403 (9)
C17	0.5845 (3)	0.4256 (2)	0.3837 (2)	0.0388 (9)
H17	0.5283	0.4382	0.4229	0.047*
C18	0.5609 (3)	0.3453 (2)	0.3357 (2)	0.0379 (8)
H18A	0.5859	0.2952	0.3658	0.045*
C19	0.6176 (3)	0.3550 (2)	0.2510 (3)	0.0411 (9)
H19	0.5653	0.3538	0.2067	0.049*
C20	0.7003 (4)	0.2693 (3)	0.1503 (3)	0.0655 (13)
H20A	0.6348	0.2541	0.1263	0.098*
H20B	0.7483	0.2234	0.1431	0.098*
H20C	0.7265	0.3192	0.1231	0.098*
C21	0.6640 (3)	0.4455 (2)	0.2540 (3)	0.0413 (9)
H21	0.6640	0.4715	0.1985	0.050*
C22	0.7736 (3)	0.3949 (3)	0.3727 (3)	0.0470 (10)
H22A	0.7645	0.3358	0.3574	0.056*
H22B	0.8393	0.4004	0.4015	0.056*
C23	0.7741 (3)	0.4501 (3)	0.2944 (3)	0.0449 (9)
C24	0.8054 (3)	0.5448 (3)	0.3170 (3)	0.0510 (10)
H24	0.8672	0.5601	0.2850	0.061*
C25	0.7206 (3)	0.6064 (3)	0.2961 (3)	0.0488 (10)
H25A	0.7130	0.6090	0.2360	0.059*
H25B	0.7405	0.6625	0.3153	0.059*
C26	0.6178 (3)	0.5833 (2)	0.3343 (3)	0.0450 (9)
H26	0.5653	0.6218	0.3117	0.054*
C27	0.6260 (5)	0.6758 (3)	0.4529 (4)	0.0805 (17)
H27A	0.6957	0.6950	0.4442	0.121*
H27B	0.6101	0.6778	0.5113	0.121*
H27C	0.5791	0.7118	0.4230	0.121*
C28	0.8615 (3)	0.4165 (3)	0.2395 (3)	0.0529 (11)
H28A	0.9270	0.4215	0.2688	0.064*
H28B	0.8499	0.3569	0.2272	0.064*
C29	0.9648 (4)	0.4617 (4)	0.1275 (3)	0.0717 (15)
H29A	1.0140	0.4871	0.1648	0.108*
H29B	0.9638	0.4927	0.0760	0.108*
H29C	0.9842	0.4038	0.1168	0.108*
C30	0.6832 (4)	0.3678 (3)	0.5058 (3)	0.0565 (11)
H30A	0.6665	0.3105	0.4904	0.085*
H30B	0.6311	0.3893	0.5429	0.085*
H30C	0.7492	0.3688	0.5332	0.085*
C31	0.2372 (4)	0.4038 (5)	0.5574 (3)	0.093 (2)
H31A	0.2842	0.3600	0.5748	0.140*
H31B	0.1695	0.3922	0.5793	0.140*
H31C	0.2609	0.4576	0.5780	0.140*
Cl1	0.44750 (9)	0.12099 (7)	0.41575 (8)	0.0623 (3)
O11	0.0250 (2)	0.51954 (19)	0.46583 (18)	0.0553 (8)
H11	0.0125	0.4738	0.4882	0.083*
C32	0.0388 (5)	0.5825 (4)	0.5277 (3)	0.0859 (18)
H32A	0.1112	0.5888	0.5394	0.129*
H32B	0.0030	0.5659	0.5776	0.129*
H32C	0.0115	0.6355	0.5081	0.129*

	U11	U22	U33	U12	U13	U23
O1	0.065 (2)	0.091 (3)	0.0468 (18)	−0.0232 (19)	0.0066 (16)	0.0031 (17)
O2	0.0363 (14)	0.0545 (16)	0.0463 (16)	−0.0098 (13)	−0.0066 (12)	0.0044 (13)
O3	0.0364 (15)	0.0546 (18)	0.078 (2)	0.0108 (14)	0.0071 (15)	0.0074 (15)
O4	0.0481 (16)	0.0467 (15)	0.0437 (16)	0.0047 (13)	−0.0087 (13)	0.0078 (12)
O5	0.0400 (15)	0.0694 (19)	0.0480 (17)	−0.0030 (14)	0.0094 (13)	0.0029 (14)
O6	0.0535 (16)	0.0353 (13)	0.0455 (16)	−0.0068 (13)	−0.0035 (13)	−0.0059 (12)
O7	0.0474 (15)	0.0444 (16)	0.0583 (19)	0.0102 (13)	0.0082 (14)	0.0005 (13)
O8	0.0550 (17)	0.0406 (14)	0.0613 (19)	−0.0047 (13)	−0.0044 (15)	−0.0061 (13)
O9	0.0442 (16)	0.0607 (19)	0.073 (2)	−0.0027 (15)	−0.0088 (15)	−0.0015 (16)
O10	0.0484 (17)	0.078 (2)	0.064 (2)	0.0129 (16)	0.0109 (15)	0.0216 (17)
N1	0.0363 (17)	0.047 (2)	0.047 (2)	0.0004 (15)	−0.0043 (14)	0.0067 (16)
C1	0.0357 (19)	0.044 (2)	0.044 (2)	−0.0035 (17)	−0.0020 (17)	−0.0013 (17)
C2	0.038 (2)	0.049 (2)	0.049 (2)	0.0003 (18)	−0.0015 (18)	−0.0070 (18)
C3	0.049 (2)	0.056 (3)	0.063 (3)	−0.003 (2)	−0.002 (2)	−0.010 (2)
C4	0.051 (3)	0.055 (3)	0.069 (3)	−0.008 (2)	−0.009 (2)	0.000 (2)
C5	0.051 (2)	0.070 (3)	0.058 (3)	−0.015 (2)	0.005 (2)	0.008 (2)
C6	0.049 (2)	0.063 (3)	0.042 (2)	−0.009 (2)	−0.001 (2)	0.001 (2)
C7	0.0338 (19)	0.052 (2)	0.049 (2)	−0.0007 (18)	−0.0068 (18)	−0.0001 (19)
C8	0.0301 (18)	0.044 (2)	0.049 (2)	−0.0122 (16)	−0.0049 (16)	0.0044 (18)
C9	0.0366 (19)	0.040 (2)	0.042 (2)	−0.0006 (16)	−0.0022 (16)	0.0031 (16)
C10	0.0326 (19)	0.0377 (19)	0.053 (2)	−0.0016 (16)	−0.0046 (17)	0.0052 (17)
C11	0.034 (2)	0.039 (2)	0.067 (3)	−0.0009 (17)	−0.0008 (18)	−0.0007 (19)
C12	0.0273 (17)	0.043 (2)	0.056 (2)	0.0056 (16)	0.0023 (17)	0.0014 (18)
C13	0.0355 (19)	0.045 (2)	0.046 (2)	−0.0002 (17)	0.0008 (17)	0.0011 (17)
C14	0.0357 (18)	0.044 (2)	0.0344 (19)	−0.0005 (17)	−0.0001 (16)	0.0054 (16)
C15	0.0406 (19)	0.0355 (18)	0.038 (2)	−0.0005 (17)	−0.0038 (16)	−0.0002 (15)
C16	0.040 (2)	0.0340 (19)	0.047 (2)	0.0036 (16)	−0.0041 (17)	0.0042 (16)
C17	0.0305 (18)	0.040 (2)	0.046 (2)	0.0014 (16)	−0.0049 (16)	0.0057 (16)
C18	0.0368 (19)	0.0338 (17)	0.043 (2)	0.0000 (16)	−0.0075 (17)	0.0036 (15)
C19	0.039 (2)	0.038 (2)	0.046 (2)	0.0066 (16)	0.0077 (17)	0.0015 (16)
C20	0.069 (3)	0.065 (3)	0.063 (3)	0.004 (3)	0.011 (3)	−0.010 (2)
C21	0.036 (2)	0.039 (2)	0.049 (2)	−0.0008 (16)	−0.0003 (17)	0.0087 (17)
C22	0.0331 (19)	0.052 (2)	0.056 (3)	0.0042 (18)	−0.0018 (18)	0.0094 (19)
C23	0.038 (2)	0.043 (2)	0.054 (2)	−0.0018 (17)	−0.0015 (18)	0.0083 (18)
C24	0.037 (2)	0.052 (2)	0.064 (3)	0.0022 (19)	−0.002 (2)	0.008 (2)
C25	0.038 (2)	0.042 (2)	0.066 (3)	−0.0072 (18)	−0.0068 (19)	0.0109 (19)
C26	0.039 (2)	0.041 (2)	0.055 (3)	−0.0004 (17)	−0.0077 (18)	0.0049 (18)
C27	0.102 (4)	0.052 (3)	0.087 (4)	−0.016 (3)	0.001 (3)	−0.017 (3)
C28	0.040 (2)	0.055 (3)	0.063 (3)	0.006 (2)	0.008 (2)	0.009 (2)
C29	0.060 (3)	0.080 (3)	0.075 (3)	0.007 (3)	0.028 (3)	0.020 (3)
C30	0.057 (3)	0.066 (3)	0.047 (2)	0.003 (2)	−0.005 (2)	0.014 (2)
C31	0.062 (3)	0.171 (7)	0.047 (3)	0.008 (4)	0.011 (2)	0.017 (4)
Cl1	0.0678 (7)	0.0509 (6)	0.0683 (8)	0.0090 (6)	0.0048 (6)	0.0101 (5)
O11	0.0571 (18)	0.0564 (18)	0.0523 (18)	−0.0034 (16)	−0.0013 (15)	0.0072 (14)
C32	0.128 (5)	0.073 (3)	0.057 (3)	−0.012 (4)	−0.008 (3)	−0.008 (3)

O1—C7	1.202 (5)	C13—H13	0.9800
O2—C7	1.342 (5)	C14—C15	1.548 (5)
O2—C8	1.434 (4)	C14—H14	0.9800
O3—C12	1.420 (4)	C15—C18	1.552 (5)
O3—H3A	0.8200	C16—C17	1.537 (5)
O4—C14	1.431 (4)	C16—C26	1.553 (5)
O4—H4A	0.8200	C16—C21	1.557 (6)
O5—C31	1.399 (5)	C17—C18	1.512 (5)
O5—C13	1.430 (4)	C17—H17	0.9800
O6—C15	1.439 (4)	C18—C19	1.551 (5)
O6—H6	0.8200	C18—H18A	0.9800
O7—C19	1.426 (4)	C19—C21	1.548 (5)
O7—C20	1.427 (5)	C19—H19	0.9800
O8—C27	1.433 (5)	C20—H20A	0.9600
O8—C26	1.436 (5)	C20—H20B	0.9600
O9—C24	1.445 (5)	C20—H20C	0.9600
O9—H9	0.8200	C21—C23	1.565 (5)
O10—C29	1.412 (5)	C21—H21	0.9800
O10—C28	1.423 (5)	C22—C23	1.528 (5)
N1—C22	1.498 (5)	C22—H22A	0.9700
N1—C30	1.497 (5)	C22—H22B	0.9700
N1—C17	1.518 (5)	C23—C28	1.526 (6)
N1—H1	0.901 (19)	C23—C24	1.587 (6)
C1—C2	1.382 (5)	C24—C25	1.501 (5)
C1—C6	1.383 (6)	C24—H24	0.9800
C1—C7	1.482 (5)	C25—C26	1.507 (5)
C2—C3	1.381 (6)	C25—H25A	0.9700
C2—H2	0.9300	C25—H25B	0.9700
C3—C4	1.383 (7)	C26—H26	0.9800
C3—H3	0.9300	C27—H27A	0.9600
C4—C5	1.386 (6)	C27—H27B	0.9600
C4—H4	0.9300	C27—H27C	0.9600
C5—C6	1.390 (6)	C28—H28A	0.9700
C5—H5	0.9300	C28—H28B	0.9700
C6—H6A	0.9300	C29—H29A	0.9600
C8—C12	1.509 (6)	C29—H29B	0.9600
C8—C9	1.532 (5)	C29—H29C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C9—C15	1.531 (5)	C30—H30B	0.9600
C9—C10	1.564 (5)	C30—H30C	0.9600
C9—H9A	0.9800	C31—H31A	0.9600
C10—C11	1.552 (6)	C31—H31B	0.9600
C10—C16	1.563 (5)	C31—H31C	0.9600
C10—H10	0.9800	O11—C32	1.414 (6)
C11—C12	1.523 (5)	O11—H11	0.8200
C11—H11A	0.9700	C32—H32A	0.9600
C11—H11B	0.9700	C32—H32B	0.9600
C12—C13	1.547 (5)	C32—H32C	0.9600
C13—C14	1.540 (5)
C7—O2—C8	119.2 (3)	N1—C17—H17	110.3
C12—O3—H3A	109.5	C16—C17—H17	110.3
C14—O4—H4A	109.5	C17—C18—C19	105.6 (3)
C31—O5—C13	115.3 (4)	C17—C18—C15	108.7 (3)
C15—O6—H6	109.5	C19—C18—C15	109.8 (3)
C19—O7—C20	111.6 (3)	C17—C18—H18A	110.9
C27—O8—C26	113.5 (3)	C19—C18—H18A	110.9
C24—O9—H9	109.5	C15—C18—H18A	110.9
C29—O10—C28	111.9 (3)	O7—C19—C21	117.5 (3)
C22—N1—C30	111.2 (3)	O7—C19—C18	111.1 (3)
C22—N1—C17	111.8 (3)	C21—C19—C18	104.2 (3)
C30—N1—C17	112.6 (3)	O7—C19—H19	107.9
C22—N1—H1	111 (3)	C21—C19—H19	107.9
C30—N1—H1	108 (3)	C18—C19—H19	107.9
C17—N1—H1	103 (3)	O7—C20—H20A	109.5
C2—C1—C6	119.3 (4)	O7—C20—H20B	109.5
C2—C1—C7	118.9 (4)	H20A—C20—H20B	109.5
C6—C1—C7	121.8 (4)	O7—C20—H20C	109.5
C1—C2—C3	121.0 (4)	H20A—C20—H20C	109.5
C1—C2—H2	119.5	H20B—C20—H20C	109.5
C3—C2—H2	119.5	C19—C21—C16	100.9 (3)
C2—C3—C4	119.4 (4)	C19—C21—C23	114.0 (3)
C2—C3—H3	120.3	C16—C21—C23	108.8 (3)
C4—C3—H3	120.3	C19—C21—H21	110.9
C3—C4—C5	120.3 (4)	C16—C21—H21	110.9
C3—C4—H4	119.9	C23—C21—H21	110.9
C5—C4—H4	119.9	N1—C22—C23	109.8 (3)
C4—C5—C6	119.6 (4)	N1—C22—H22A	109.7
C4—C5—H5	120.2	C23—C22—H22A	109.7
C6—C5—H5	120.2	N1—C22—H22B	109.7
C1—C6—C5	120.3 (4)	C23—C22—H22B	109.7
C1—C6—H6A	119.8	H22A—C22—H22B	108.2
C5—C6—H6A	119.8	C28—C23—C22	106.3 (3)
O1—C7—O2	123.3 (4)	C28—C23—C21	114.7 (3)
O1—C7—C1	125.1 (4)	C22—C23—C21	108.1 (3)
O2—C7—C1	111.5 (3)	C28—C23—C24	105.6 (3)
O2—C8—C12	109.4 (3)	C22—C23—C24	110.3 (3)
O2—C8—C9	116.6 (3)	C21—C23—C24	111.7 (3)
C12—C8—C9	102.1 (3)	O9—C24—C25	107.5 (4)
O2—C8—H8	109.5	O9—C24—C23	111.8 (3)
C12—C8—H8	109.5	C25—C24—C23	111.7 (3)
C9—C8—H8	109.5	O9—C24—H24	108.6
C8—C9—C15	112.4 (3)	C25—C24—H24	108.6
C8—C9—C10	101.2 (3)	C23—C24—H24	108.6
C15—C9—C10	112.9 (3)	C24—C25—C26	113.3 (3)
C8—C9—H9A	110.0	C24—C25—H25A	108.9
C15—C9—H9A	110.0	C26—C25—H25A	108.9
C10—C9—H9A	110.0	C24—C25—H25B	108.9
C11—C10—C16	112.2 (3)	C26—C25—H25B	108.9
C11—C10—C9	103.2 (3)	H25A—C25—H25B	107.7
C16—C10—C9	118.9 (3)	O8—C26—C25	113.7 (3)
C11—C10—H10	107.3	O8—C26—C16	107.0 (3)
C16—C10—H10	107.3	C25—C26—C16	111.9 (3)
C9—C10—H10	107.3	O8—C26—H26	108.0
C12—C11—C10	107.3 (3)	C25—C26—H26	108.0
C12—C11—H11A	110.2	C16—C26—H26	108.0
C10—C11—H11A	110.2	O8—C27—H27A	109.5
C12—C11—H11B	110.2	O8—C27—H27B	109.5
C10—C11—H11B	110.2	H27A—C27—H27B	109.5
H11A—C11—H11B	108.5	O8—C27—H27C	109.5
O3—C12—C8	113.3 (3)	H27A—C27—H27C	109.5
O3—C12—C11	109.0 (3)	H27B—C27—H27C	109.5
C8—C12—C11	100.3 (3)	O10—C28—C23	109.6 (3)
O3—C12—C13	111.6 (3)	O10—C28—H28A	109.7
C8—C12—C13	110.2 (3)	C23—C28—H28A	109.7
C11—C12—C13	111.9 (3)	O10—C28—H28B	109.7
O5—C13—C14	107.7 (3)	C23—C28—H28B	109.7
O5—C13—C12	108.6 (3)	H28A—C28—H28B	108.2
C14—C13—C12	114.6 (3)	O10—C29—H29A	109.5
O5—C13—H13	108.6	O10—C29—H29B	109.5
C14—C13—H13	108.6	H29A—C29—H29B	109.5
C12—C13—H13	108.6	O10—C29—H29C	109.5
O4—C14—C13	107.0 (3)	H29A—C29—H29C	109.5
O4—C14—C15	112.3 (3)	H29B—C29—H29C	109.5
C13—C14—C15	117.7 (3)	N1—C30—H30A	109.5
O4—C14—H14	106.4	N1—C30—H30B	109.5
C13—C14—H14	106.4	H30A—C30—H30B	109.5
C15—C14—H14	106.4	N1—C30—H30C	109.5
O6—C15—C9	105.0 (3)	H30A—C30—H30C	109.5
O6—C15—C14	109.3 (3)	H30B—C30—H30C	109.5
C9—C15—C14	111.8 (3)	O5—C31—H31A	109.5
O6—C15—C18	107.8 (3)	O5—C31—H31B	109.5
C9—C15—C18	108.3 (3)	H31A—C31—H31B	109.5
C14—C15—C18	114.1 (3)	O5—C31—H31C	109.5
C17—C16—C26	117.4 (3)	H31A—C31—H31C	109.5
C17—C16—C21	98.4 (3)	H31B—C31—H31C	109.5
C26—C16—C21	112.9 (3)	C32—O11—H11	109.5
C17—C16—C10	106.4 (3)	O11—C32—H32A	109.5
C26—C16—C10	106.2 (3)	O11—C32—H32B	109.5
C21—C16—C10	115.6 (3)	H32A—C32—H32B	109.5
C18—C17—N1	112.9 (3)	O11—C32—H32C	109.5
C18—C17—C16	100.5 (3)	H32A—C32—H32C	109.5
N1—C17—C16	112.1 (3)	H32B—C32—H32C	109.5
C18—C17—H17	110.3

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5	0.82	2.11	2.612 (4)	119
O3—H3A···O11	0.82	2.22	2.923 (4)	144
O4—H4A···Cl1	0.82	2.30	3.083 (3)	161
O6—H6···Cl1	0.82	2.40	3.197 (3)	165
O9—H9···O11i	0.82	1.98	2.776 (4)	163
N1—H1···O8	0.90 (2)	2.11 (4)	2.808 (4)	134 (4)
N1—H1···O9	0.90 (2)	2.20 (4)	2.795 (5)	123 (4)
O11—H11···Cl1ii	0.82	2.30	3.084 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5	0.82	2.11	2.612 (4)	119
O3—H3A⋯O11	0.82	2.22	2.923 (4)	144
O4—H4A⋯Cl1	0.82	2.30	3.083 (3)	161
O6—H6⋯Cl1	0.82	2.40	3.197 (3)	165
O9—H9⋯O11i	0.82	1.98	2.776 (4)	163
N1—H1⋯O8	0.90 (2)	2.11 (4)	2.808 (4)	134 (4)
N1—H1⋯O9	0.90 (2)	2.20 (4)	2.795 (5)	123 (4)
O11—H11⋯Cl1ii	0.82	2.30	3.084 (3)	158

Symmetry codes: (i) ; (ii) .