[(1R*,3S*,4S*)-3-(2-Hy­droxy­benzo­yl)-1,2,3,4-tetra­hydro-1,4-ep­oxy­naphthalen-1-yl]methyl 4-nitro­benzoate

Lough, A.J.; Ho, A.; Tam, W.

doi:10.1107/S2414314620002655

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 2| February 2020| x200265

https://doi.org/10.1107/S2414314620002655

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[(1R,3S,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate

Alan J. Lough,^a ^* Angel Ho ^b and William Tam ^b

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and ^bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
^*Correspondence e-mail: alan.lough@utoronto.ca

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 February 2020; accepted 25 February 2020; online 28 February 2020)

The relative stereo- and regiochemistry of the racemic title compound, C₂₅H₁₉NO₇, were established from the crystal structure. The fused benzene ring forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hydroxy-substituted benzene ring and the nitro-substituted benzene ring, respectively. The dihedral angle between the hydroxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intramolecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules, forming layers parallel to (100). Within these layers, there are weak π–π stacking interactions with a ring centroid–ring centroid distance of 3.555 (1) Å.

Keywords: crystal structure; regioselectivity; weak hydrogen bonding.

CCDC reference: 1986297

Structure description

In past years, our research group (Ballantine et al., 2009 ; Edmunds et al., 2015 ; Hill & Tam, 2019 ; Edmunds et al., 2016 ; Raheem et al., 2014 ) has investigated the effects of various C₁-substituted oxabenzonorbornadienes (OBD) on controlling the regioselectivity of ring-opening reactions. In 2015 , Nagamoto and Nishimura reported the iridium-catalysed hydroacylation reaction of bicyclic alkenes with 2-hydroxybenzaldehyde and its derivatives. Based upon these findings, we set out to determine the effect of C₁ substitution on controlling the regioselectivity in the iridium-catalysed hydroacylation reaction with salicylaldehyde II (see Fig. 1) on unsymmetrical oxabenzonorbornadienes. Reaction of C₁-substituted OBD (I) with salicylaldehyde II in the presence of [Ir(COD)Cl]₂ (COD = 1,5-cyclooctaiene), and 5 M KOH afforded exclusively the title C₃ regioisomer (III) in a 82% yield. The relative stereo- and regiochemistry of the adduct system was determined by single-crystal X-ray analysis. There are two possible stereoisomers as the addition can occur on the exo or the endo face, and two possible regioisomers as the addition can occur at the C₂ or C₃ position. Of the four possible stereo- and regio-isomers, only the exo-C₃ isomer was obtained. The title compound is racemic: in the arbitrarily chosen asymmetric unit, the stereogenic centres are as follows: C1 R; C3 S; C4 S.

Figure 1
The reaction scheme.

The molecular structure of the title compound is shown in Fig. 2. The fused benzene ring (C5–C10) forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hydroxy-substituted benzene ring (C12–C17) and the nitro-substituted benzene ring (C20–C25), respectively. The dihedral angle between the hydroxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intramolecular O—H⋯O hydrogen bond is observed. In the crystal, weak C—H⋯O hydrogen bonds (Table 1) connect the molecules, forming layers lying parallel to (100) (Fig. 3). Within these layers, there are weak π–π stacking interactions with a ring centroid–ring centroid distance of 3.555 (1) Å for Cg⋯Cg(1 − x, −y, 1 − z) where Cg is the centroid of the C20–C25 ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2	0.94 (2)	1.67 (2)	2.5321 (15)	151.7 (19)
C3—H3A⋯O3ⁱ	1.00	2.48	3.4510 (17)	163
C8—H8A⋯O1ⁱⁱ	0.95	2.38	3.2782 (17)	157
C9—H9A⋯O7ⁱⁱⁱ	0.95	2.49	3.4057 (19)	161
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Figure 2
The molecular structure of the title compound with displacement ellipsoids drawn the 30% probability level.

Figure 3
Part of the crystal structure with weak hydrogen bonds shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.

Synthesis and crystallization

To a dried screw-cap vial, was added [Ir(COD)Cl]₂ (10 mg, 5 mol%), C₁-substituted oxabenzonorbornadiene (I) (Fig. 1) (0.3 mmol, 1.2 equiv.), salicylaldehyde II (27 µl, 1 equiv.) and 5M KOH (0.03 mmol, 10 mol%) dissolved in 2 ml of 1,4-dioxane. The reaction was left to stir at 338 K for 20 h, the resultant mixture was loaded directly onto a column and the crude reaction mixture was purified by flash chromatography (EtOAc:hexanes 25:75) to obtain the adduct product III (101 mg, 0.23 mmol, 82%) as a yellow solid. The product was then subsequently recrystallized from solution in pure hexanes by slow evaporation of the solvent to give product III as colourless crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₁₉NO₇
M_r	445.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.7455 (10), 11.9504 (8), 11.9649 (8)
β (°)	101.898 (2)
V (Å³)	2063.1 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.30 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX DUO PHOTON II
Absorption correction	Multi-scan (Krause et al., 2015 )
T_min, T_max	0.623, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	40054, 4727, 3399
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.093, 1.01
No. of reflections	4727
No. of parameters	302
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2019 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1986297

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620002655/hb4338sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620002655/hb4338Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620002655/hb4338Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2019); cell refinement: APEX3 (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

[(1R*,3S*,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate top

Crystal data top

C₂₅H₁₉NO₇	F(000) = 928
M_r = 445.41	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7455 (10) Å	Cell parameters from 9213 reflections
b = 11.9504 (8) Å	θ = 2.4–27.2°
c = 11.9649 (8) Å	µ = 0.11 mm⁻¹
β = 101.898 (2)°	T = 150 K
V = 2063.1 (2) Å³	Shard, colourless
Z = 4	0.32 × 0.30 × 0.16 mm

Data collection top

Bruker Kappa APEX DUO PHOTON II diffractometer	3399 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	R_int = 0.059
φ and ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (Krause et al., 2015)	h = −19→19
T_min = 0.623, T_max = 0.746	k = −15→15
40054 measured reflections	l = −15→15
4727 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.039P)² + 0.5845P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4727 reflections	Δρ_max = 0.25 e Å⁻³
302 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.21520 (6)	0.45410 (8)	0.52221 (8)	0.0254 (2)
O2	0.09918 (8)	0.66077 (8)	0.55530 (9)	0.0357 (3)
O3	0.08195 (8)	0.86474 (10)	0.60434 (9)	0.0376 (3)
H3O	0.0802 (14)	0.7862 (18)	0.6067 (18)	0.069 (6)*
O4	0.37771 (6)	0.32000 (8)	0.53811 (9)	0.0295 (2)
O5	0.53204 (7)	0.32594 (9)	0.60060 (9)	0.0336 (2)
O6	0.35631 (8)	−0.23766 (9)	0.63820 (10)	0.0430 (3)
O7	0.50514 (8)	−0.25121 (9)	0.65612 (9)	0.0393 (3)
N1	0.43308 (9)	−0.19667 (10)	0.64302 (10)	0.0317 (3)
C1	0.27856 (9)	0.46052 (11)	0.44429 (11)	0.0239 (3)
C2	0.26049 (9)	0.58196 (11)	0.39894 (12)	0.0247 (3)
H2A	0.275088	0.590603	0.322264	0.030*
H2B	0.296733	0.637046	0.451839	0.030*
C3	0.15431 (9)	0.59376 (11)	0.39449 (11)	0.0238 (3)
H3A	0.120016	0.605331	0.314073	0.029*
C4	0.13143 (9)	0.47745 (11)	0.43864 (12)	0.0249 (3)
H4A	0.072919	0.474098	0.468439	0.030*
C5	0.13776 (9)	0.39344 (11)	0.34635 (12)	0.0249 (3)
C6	0.07283 (10)	0.33873 (12)	0.26533 (13)	0.0302 (3)
H6A	0.008319	0.348599	0.261361	0.036*
C7	0.10549 (11)	0.26840 (12)	0.18949 (13)	0.0332 (3)
H7A	0.062396	0.228731	0.133444	0.040*
C8	0.19923 (11)	0.25522 (12)	0.19418 (12)	0.0319 (3)
H8A	0.219548	0.206293	0.141757	0.038*
C9	0.26456 (10)	0.31274 (11)	0.27481 (12)	0.0283 (3)
H9A	0.329065	0.304773	0.277455	0.034*
C10	0.23228 (9)	0.38140 (11)	0.35039 (11)	0.0235 (3)
C11	0.13163 (9)	0.68588 (11)	0.47082 (11)	0.0254 (3)
C12	0.14368 (9)	0.80400 (11)	0.44234 (12)	0.0250 (3)
C13	0.11508 (10)	0.88844 (12)	0.50972 (12)	0.0283 (3)
C14	0.11990 (10)	1.00024 (12)	0.47954 (14)	0.0349 (4)
H14A	0.100414	1.056998	0.524970	0.042*
C15	0.15290 (11)	1.02872 (12)	0.38389 (14)	0.0369 (4)
H15A	0.155158	1.105273	0.363255	0.044*
C16	0.18300 (10)	0.94724 (12)	0.31691 (13)	0.0340 (3)
H16A	0.206590	0.967947	0.251714	0.041*
C17	0.17825 (10)	0.83600 (12)	0.34613 (12)	0.0287 (3)
H17A	0.198678	0.780174	0.300444	0.034*
C18	0.37610 (10)	0.43650 (11)	0.50427 (12)	0.0279 (3)
H18A	0.419456	0.449528	0.452497	0.034*
H18B	0.394223	0.485260	0.572100	0.034*
C19	0.46027 (9)	0.27418 (12)	0.57989 (11)	0.0253 (3)
C20	0.45169 (9)	0.15105 (11)	0.59774 (11)	0.0247 (3)
C21	0.36672 (9)	0.09770 (12)	0.56869 (12)	0.0274 (3)
H21A	0.312763	0.139404	0.536667	0.033*
C22	0.36020 (10)	−0.01641 (12)	0.58624 (12)	0.0287 (3)
H22A	0.302095	−0.053641	0.568005	0.034*
C23	0.44020 (10)	−0.07438 (12)	0.63079 (11)	0.0273 (3)
C24	0.52603 (10)	−0.02386 (12)	0.65983 (12)	0.0293 (3)
H24A	0.579934	−0.066435	0.689955	0.035*
C25	0.53146 (10)	0.09052 (12)	0.64388 (12)	0.0284 (3)
H25A	0.589463	0.127695	0.664342	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (5)	0.0252 (5)	0.0235 (5)	0.0008 (4)	0.0085 (4)	0.0022 (4)
O2	0.0536 (7)	0.0288 (5)	0.0292 (5)	0.0063 (5)	0.0189 (5)	0.0028 (4)
O3	0.0493 (7)	0.0330 (6)	0.0332 (6)	0.0069 (5)	0.0145 (5)	−0.0052 (5)
O4	0.0247 (5)	0.0248 (5)	0.0380 (6)	0.0019 (4)	0.0040 (4)	0.0041 (4)
O5	0.0259 (5)	0.0370 (6)	0.0358 (6)	−0.0032 (5)	0.0019 (4)	0.0034 (5)
O6	0.0423 (7)	0.0330 (6)	0.0484 (7)	−0.0031 (5)	−0.0029 (5)	0.0024 (5)
O7	0.0485 (7)	0.0354 (6)	0.0344 (6)	0.0168 (5)	0.0097 (5)	0.0035 (5)
N1	0.0408 (8)	0.0302 (7)	0.0224 (6)	0.0058 (6)	0.0027 (5)	−0.0004 (5)
C1	0.0258 (7)	0.0230 (7)	0.0245 (7)	−0.0012 (5)	0.0085 (6)	0.0011 (5)
C2	0.0277 (7)	0.0212 (6)	0.0260 (7)	−0.0009 (5)	0.0074 (6)	0.0007 (5)
C3	0.0272 (7)	0.0219 (7)	0.0228 (7)	0.0008 (5)	0.0059 (5)	0.0002 (5)
C4	0.0236 (7)	0.0241 (7)	0.0278 (7)	0.0015 (5)	0.0072 (6)	0.0017 (6)
C5	0.0278 (7)	0.0193 (6)	0.0280 (7)	−0.0008 (5)	0.0069 (6)	0.0025 (5)
C6	0.0279 (7)	0.0254 (7)	0.0360 (8)	−0.0022 (6)	0.0036 (6)	0.0018 (6)
C7	0.0402 (9)	0.0258 (7)	0.0307 (8)	−0.0053 (6)	0.0007 (7)	−0.0019 (6)
C8	0.0441 (9)	0.0242 (7)	0.0284 (7)	0.0012 (6)	0.0098 (7)	−0.0032 (6)
C9	0.0311 (8)	0.0251 (7)	0.0305 (8)	0.0010 (6)	0.0105 (6)	0.0011 (6)
C10	0.0265 (7)	0.0202 (6)	0.0242 (7)	−0.0012 (5)	0.0058 (5)	0.0031 (5)
C11	0.0273 (7)	0.0263 (7)	0.0220 (7)	0.0039 (6)	0.0036 (6)	0.0020 (6)
C12	0.0250 (7)	0.0240 (7)	0.0239 (7)	0.0026 (5)	0.0003 (5)	0.0000 (5)
C13	0.0268 (7)	0.0280 (7)	0.0279 (7)	0.0035 (6)	0.0010 (6)	−0.0021 (6)
C14	0.0317 (8)	0.0259 (7)	0.0440 (9)	0.0040 (6)	0.0005 (7)	−0.0062 (7)
C15	0.0372 (9)	0.0223 (7)	0.0460 (9)	0.0010 (6)	−0.0032 (7)	0.0046 (7)
C16	0.0354 (8)	0.0305 (8)	0.0338 (8)	−0.0035 (6)	0.0015 (7)	0.0066 (6)
C17	0.0307 (7)	0.0267 (7)	0.0269 (7)	−0.0006 (6)	0.0018 (6)	0.0006 (6)
C18	0.0282 (7)	0.0227 (7)	0.0322 (8)	−0.0011 (6)	0.0044 (6)	0.0022 (6)
C19	0.0237 (7)	0.0326 (8)	0.0197 (7)	0.0025 (6)	0.0049 (5)	−0.0008 (6)
C20	0.0265 (7)	0.0281 (7)	0.0200 (6)	0.0027 (6)	0.0060 (5)	−0.0010 (5)
C21	0.0244 (7)	0.0293 (7)	0.0286 (7)	0.0057 (6)	0.0053 (6)	−0.0008 (6)
C22	0.0269 (7)	0.0287 (7)	0.0305 (7)	0.0004 (6)	0.0058 (6)	−0.0025 (6)
C23	0.0336 (8)	0.0277 (7)	0.0208 (7)	0.0061 (6)	0.0062 (6)	−0.0002 (5)
C24	0.0289 (8)	0.0335 (8)	0.0243 (7)	0.0090 (6)	0.0030 (6)	0.0004 (6)
C25	0.0248 (7)	0.0344 (8)	0.0251 (7)	0.0023 (6)	0.0035 (6)	−0.0018 (6)

Geometric parameters (Å, º) top

O1—C4	1.4471 (16)	C8—C9	1.396 (2)
O1—C1	1.4515 (15)	C8—H8A	0.9500
O2—C11	1.2410 (16)	C9—C10	1.3766 (19)
O3—C13	1.3523 (18)	C9—H9A	0.9500
O3—H3O	0.94 (2)	C11—C12	1.4715 (19)
O4—C19	1.3345 (16)	C12—C17	1.405 (2)
O4—C18	1.4487 (16)	C12—C13	1.4093 (19)
O5—C19	1.2066 (16)	C13—C14	1.390 (2)
O6—N1	1.2238 (16)	C14—C15	1.375 (2)
O7—N1	1.2287 (15)	C14—H14A	0.9500
N1—C23	1.4746 (19)	C15—C16	1.391 (2)
C1—C18	1.4968 (19)	C15—H15A	0.9500
C1—C10	1.5185 (18)	C16—C17	1.380 (2)
C1—C2	1.5531 (18)	C16—H16A	0.9500
C2—C3	1.5620 (19)	C17—H17A	0.9500
C2—H2A	0.9900	C18—H18A	0.9900
C2—H2B	0.9900	C18—H18B	0.9900
C3—C11	1.5112 (18)	C19—C20	1.4959 (19)
C3—C4	1.5486 (18)	C20—C21	1.3848 (19)
C3—H3A	1.0000	C20—C25	1.3942 (19)
C4—C5	1.5095 (19)	C21—C22	1.386 (2)
C4—H4A	1.0000	C21—H21A	0.9500
C5—C6	1.3788 (19)	C22—C23	1.3770 (19)
C5—C10	1.3920 (19)	C22—H22A	0.9500
C6—C7	1.393 (2)	C23—C24	1.380 (2)
C6—H6A	0.9500	C24—C25	1.385 (2)
C7—C8	1.381 (2)	C24—H24A	0.9500
C7—H7A	0.9500	C25—H25A	0.9500

C4—O1—C1	96.71 (9)	O2—C11—C12	120.38 (12)
C13—O3—H3O	104.6 (13)	O2—C11—C3	119.12 (12)
C19—O4—C18	117.40 (11)	C12—C11—C3	120.43 (12)
O6—N1—O7	124.11 (13)	C17—C12—C13	118.41 (13)
O6—N1—C23	118.42 (12)	C17—C12—C11	122.17 (12)
O7—N1—C23	117.46 (13)	C13—C12—C11	119.33 (13)
O1—C1—C18	111.35 (11)	O3—C13—C14	117.75 (13)
O1—C1—C10	101.05 (10)	O3—C13—C12	122.09 (13)
C18—C1—C10	118.44 (11)	C14—C13—C12	120.16 (14)
O1—C1—C2	100.78 (10)	C15—C14—C13	119.99 (14)
C18—C1—C2	115.17 (11)	C15—C14—H14A	120.0
C10—C1—C2	107.74 (11)	C13—C14—H14A	120.0
C1—C2—C3	101.24 (10)	C14—C15—C16	121.06 (14)
C1—C2—H2A	111.5	C14—C15—H15A	119.5
C3—C2—H2A	111.5	C16—C15—H15A	119.5
C1—C2—H2B	111.5	C17—C16—C15	119.31 (15)
C3—C2—H2B	111.5	C17—C16—H16A	120.3
H2A—C2—H2B	109.3	C15—C16—H16A	120.3
C11—C3—C4	110.90 (11)	C16—C17—C12	121.05 (14)
C11—C3—C2	112.98 (11)	C16—C17—H17A	119.5
C4—C3—C2	101.22 (10)	C12—C17—H17A	119.5
C11—C3—H3A	110.5	O4—C18—C1	106.08 (11)
C4—C3—H3A	110.5	O4—C18—H18A	110.5
C2—C3—H3A	110.5	C1—C18—H18A	110.5
O1—C4—C5	101.80 (10)	O4—C18—H18B	110.5
O1—C4—C3	101.18 (10)	C1—C18—H18B	110.5
C5—C4—C3	107.26 (11)	H18A—C18—H18B	108.7
O1—C4—H4A	115.0	O5—C19—O4	124.08 (13)
C5—C4—H4A	115.0	O5—C19—C20	124.85 (12)
C3—C4—H4A	115.0	O4—C19—C20	111.08 (11)
C6—C5—C10	121.37 (13)	C21—C20—C25	120.42 (13)
C6—C5—C4	133.71 (13)	C21—C20—C19	121.05 (12)
C10—C5—C4	104.82 (11)	C25—C20—C19	118.53 (12)
C5—C6—C7	117.43 (13)	C20—C21—C22	120.16 (13)
C5—C6—H6A	121.3	C20—C21—H21A	119.9
C7—C6—H6A	121.3	C22—C21—H21A	119.9
C8—C7—C6	121.32 (14)	C23—C22—C21	118.22 (13)
C8—C7—H7A	119.3	C23—C22—H22A	120.9
C6—C7—H7A	119.3	C21—C22—H22A	120.9
C7—C8—C9	120.95 (13)	C22—C23—C24	123.04 (14)
C7—C8—H8A	119.5	C22—C23—N1	117.66 (13)
C9—C8—H8A	119.5	C24—C23—N1	119.26 (12)
C10—C9—C8	117.70 (13)	C23—C24—C25	118.24 (13)
C10—C9—H9A	121.2	C23—C24—H24A	120.9
C8—C9—H9A	121.2	C25—C24—H24A	120.9
C9—C10—C5	121.20 (13)	C24—C25—C20	119.91 (13)
C9—C10—C1	133.92 (12)	C24—C25—H25A	120.0
C5—C10—C1	104.80 (11)	C20—C25—H25A	120.0

C4—O1—C1—C18	−178.46 (11)	O2—C11—C12—C17	−178.58 (13)
C4—O1—C1—C10	−51.79 (11)	C3—C11—C12—C17	−1.5 (2)
C4—O1—C1—C2	58.90 (11)	O2—C11—C12—C13	−2.1 (2)
O1—C1—C2—C3	−35.63 (12)	C3—C11—C12—C13	174.94 (12)
C18—C1—C2—C3	−155.56 (11)	C17—C12—C13—O3	−179.28 (12)
C10—C1—C2—C3	69.79 (12)	C11—C12—C13—O3	4.1 (2)
C1—C2—C3—C11	118.93 (12)	C17—C12—C13—C14	1.1 (2)
C1—C2—C3—C4	0.30 (12)	C11—C12—C13—C14	−175.51 (13)
C1—O1—C4—C5	51.61 (11)	O3—C13—C14—C15	−179.85 (13)
C1—O1—C4—C3	−58.89 (11)	C12—C13—C14—C15	−0.2 (2)
C11—C3—C4—O1	−84.83 (12)	C13—C14—C15—C16	−0.9 (2)
C2—C3—C4—O1	35.28 (12)	C14—C15—C16—C17	1.0 (2)
C11—C3—C4—C5	168.93 (11)	C15—C16—C17—C12	−0.1 (2)
C2—C3—C4—C5	−70.96 (12)	C13—C12—C17—C16	−0.9 (2)
O1—C4—C5—C6	151.71 (15)	C11—C12—C17—C16	175.55 (13)
C3—C4—C5—C6	−102.49 (17)	C19—O4—C18—C1	171.18 (11)
O1—C4—C5—C10	−32.04 (13)	O1—C1—C18—O4	66.60 (13)
C3—C4—C5—C10	73.76 (13)	C10—C1—C18—O4	−49.87 (15)
C10—C5—C6—C7	1.7 (2)	C2—C1—C18—O4	−179.47 (11)
C4—C5—C6—C7	177.47 (14)	C18—O4—C19—O5	6.95 (19)
C5—C6—C7—C8	−0.9 (2)	C18—O4—C19—C20	−173.23 (11)
C6—C7—C8—C9	−0.5 (2)	O5—C19—C20—C21	−178.22 (13)
C7—C8—C9—C10	1.0 (2)	O4—C19—C20—C21	1.96 (18)
C8—C9—C10—C5	−0.2 (2)	O5—C19—C20—C25	1.4 (2)
C8—C9—C10—C1	−176.44 (14)	O4—C19—C20—C25	−178.39 (11)
C6—C5—C10—C9	−1.2 (2)	C25—C20—C21—C22	0.6 (2)
C4—C5—C10—C9	−178.00 (12)	C19—C20—C21—C22	−179.80 (13)
C6—C5—C10—C1	176.00 (12)	C20—C21—C22—C23	−1.2 (2)
C4—C5—C10—C1	−0.82 (13)	C21—C22—C23—C24	0.8 (2)
O1—C1—C10—C9	−150.10 (15)	C21—C22—C23—N1	−176.67 (12)
C18—C1—C10—C9	−28.3 (2)	O6—N1—C23—C22	−16.19 (19)
C2—C1—C10—C9	104.67 (17)	O7—N1—C23—C22	162.95 (12)
O1—C1—C10—C5	33.25 (12)	O6—N1—C23—C24	166.29 (13)
C18—C1—C10—C5	155.09 (12)	O7—N1—C23—C24	−14.57 (18)
C2—C1—C10—C5	−71.98 (13)	C22—C23—C24—C25	0.4 (2)
C4—C3—C11—O2	−0.02 (17)	N1—C23—C24—C25	177.78 (12)
C2—C3—C11—O2	−112.86 (14)	C23—C24—C25—C20	−1.1 (2)
C4—C3—C11—C12	−177.14 (12)	C21—C20—C25—C24	0.6 (2)
C2—C3—C11—C12	70.02 (15)	C19—C20—C25—C24	−179.03 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.94 (2)	1.67 (2)	2.5321 (15)	151.7 (19)
C3—H3A···O3ⁱ	1.00	2.48	3.4510 (17)	163
C8—H8A···O1ⁱⁱ	0.95	2.38	3.2782 (17)	157
C9—H9A···O7ⁱⁱⁱ	0.95	2.49	3.4057 (19)	161

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1.

Acknowledgements

The University of Toronto thanks NSERC Canada for funding.

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