4,5,6,9-Tetra­methoxy-11-phenyl-10-oxa-11-aza­tri­cyclo­[7.2.2.0^2,7]­trideca-2(7),3,5,12-tetraen-8-one

The crystal structure of the adduct, C₂₁H₂₁NO₂, of tetra­methyl­purpurogallin with nitro­so­benzene is reported. The compound exhibits a [3.2.2] bicyclic system corresponding to two seven-membered rings and one six-membered ring in distorted chair, boat and twist-boat conformations, respectively. One intramolecular and two intermolecular hydrogen bonds direct the packing and stabilize the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.145
• Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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S1. Comment

Continuing our studies on Diels–Alder reactions using NO compounds as dienophiles as the key reaction directed towards the total synthesis of naturally occurring alkaloids (Russi et al., 2000), we report in this work the structure of the adduct, (I), between tetramethylpurpurogallin, a synthetic benzotropolone, and nitrosobenzene. The regiochemistry of the cycloaddition reaction is strongly dependent on stereo-electronic factors and can be analyzed by spectroscopic methods and X-ray diffraction. However, crystal structure determination is the only study that provides conclusive results about the conformation of the molecule. The NO bridge has the same orientation towards the carbonyl group as in the case of the eucarvone adduct. The O atom of the dienophile adds to C9, α to the carbonyl, and the N atom adds to the benzyllic C1 atom exclusively, yielding only the exo adduct.

The adduct shows the characteristic [3.2.2] bicyclic system present in other similar compounds (Tinant & Declercq, 1991a,b; Russi et al., 2000). Selected bond distances, endocyclic angles and torsion angles are given in Table 1. The six-membered ring exhibits a distorted twist–boat conformation. The puckering parameters (Cremer & Pople, 1975) for this ring are q₂ = 0.617 Å, q₃ = 0.125 Å, ϕ₂ = 100.41°, θ = 78.6 ° and Q_T = 0.630 Å. The seven-membered ring with the C12═C13 double bond has a distorted chair conformation (q₂ = 0.932 Å, q₃ = 0.354 Å, ϕ₂ = 322.65°, ϕ₃ = 58.71° and Q_T = 0.997 Å), and the one containing the N—O is a distorted boat (q₂ = 1.003 Å, q₃ = 0.313 Å, ϕ₂ = 322.77°, ϕ₃ = 290.06° and Q_T = 1.051 Å).

As in the eucarvone adduct (Russi et al., 2000), there is not conjugation between the phenyl group and the NO. The N atom is pyramidal and is located 0.444 (2) Å from the C1/O10/C1' plane. The N—O bond length is 1.434 (2) Å and the distance between O10 and the phenyl-group plane is 0.506 (1) Å (longer than in the eucarvone adduct).

The ring bonded to the [3.2.2] bicyclic system is planar and the maximum deviation from this plane is 0.012 (1) Å for C4. Steric factors place two of the C atoms belonging to the methoxy groups (C41 and C61) above the ring plane, while the other one (C51) is placed below. The dihedral angles are -161.8 (2)° for C5—C4—O41—C41, -91.7 (2)° for C7—C6—O61—C61 and 85.5 (3)° for C6—C5—O51—C51.

The combination of electronic and steric factors direct the cycloaddition to give a compound whose structure explains the spectral data (¹H and ¹³C NMR) obtained, as the deshielding of H1 and H12 by an anisotropic effect due to the orientation of the phenyl group.

S2. Experimental

Tetra-O-methyl purpurogallin (Baltrop & Nichols, 1948) (1.11 g, 4.02 mmol) and nitrosobenzene (0.52 g, 4.86 mmol) were dissolved in hexane (50 ml). The solution was left standing at room temperature, in the absence of light, for 40 h. The white crystals obtained were filtered and recrystallized from methanol to yield the tetra-O-methylpurpurogallin–nitrosobenzene adduct (1.39 g, 90%; m.p. 387–388 K). The filtrate was concentrated under vacuum and the crystals obtained were recrystallized from methanol (160 mg, 10%).

S3. Refinement

H atoms were located at geometrically suitable positions and refined with fixed isotropic displacement parameters U_iso = 1.2U_eq of the parent atom.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Pritzkow, 1995); software used to prepare material for publication: PLATON (Spek, 1990) and CSD (Allen & Kennard, 1993).

Figures

Fig. 1. ZORTEP drawing (Zsolnai & Pritzkow, 1995) of the molecular structure of (I) showing 30% probability displacement ellipsoids.

4,5,6,9-tetramethoxy-11-phenyl-10-oxa-11-aza-tricyclo[7.2.2.0 2,7] trideca-2(7),3,5,12-tetraen-8-one

Crystal data

C21H21NO6	Dx = 1.355 Mg m^−3
Mr = 383.39	Melting point: 387-388 K K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 13.495 (2) Å	Cell parameters from 25 reflections
b = 10.2178 (18) Å	θ = 22.8–34.0°
c = 15.154 (3) Å	µ = 0.10 mm^−1
β = 115.956 (14)°	T = 293 K
V = 1878.8 (6) Å^3	Prismatic, colourless
Z = 4	0.15 × 0.12 × 0.10 mm
F(000) = 808

Data collection

Rigaku AFC-7S diffractometer	Rint = 0.047
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.5°
Graphite monochromator	h = −1→17
θ/2θ scans	k = −1→13
5381 measured reflections	l = −19→18
4300 independent reflections	3 standard reflections every 150 reflections
2466 reflections with I > 2σ(I)	intensity decay: 8.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.3861P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4300 reflections	Δρmax = 0.22 e Å^−3
259 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (15)

Special details

Experimental. IR (Shimadzu FT—IR DR-8031, KBr):ν (cm^-1)=3003.5, 2982.3, 2943.7, 1693.7, 1589.5, 1491.2, 1456.4, 1402.4, 1356.1, 1325.3, 1282.8, 1257.7, 1215.3, 1197.9, 1134.3, 1107.3, 1088.0, 1049.4, 1032.0, 987.7, 954.9, 918.2, 898.9, 877.7, 841.1, 806.3, 763.9, 694.5, 655.9.

MS (Shimadzu GC—MS QP 1100 EX, ID, IE; 70 eV, 298 K) m/z= 276(83%); 261(17%); 248(32%); 233(24%); 218(65%); 205(20%); 190(15%); 173(11%); 161(14%); 147(9%); 131(7%); 115(10%); 107(PhNO⁺, 62%); 77 (Ph⁺, 100%), 51(52%). Found: C: 65.8%; H: 5.8%; N: 3.7%. Requires: C: 65.8%, H: 5.5%; N: 3.7%. ν_max (CH₂Cl₂) 1696, 1586 cm^-1. ν_max (nujol) 1700, 1585 cm^-1. λ_max (methanol) 245, 296 µm (ε=26500 and 10500 respectively).

¹H NMR (CDCl₃, 400 MHz, Bruker Avance DPX400: δ(p.p.m.)= 7.21 (dd; J₁= 7.8 Hz, J₂= 7.3 Hz, H'3, H'5); 7.09 (dd; J₁= 8.6 Hz, J₂= 1.0 Hz, H'2, H'6); 6.93 (d; J= 7.3 Hz, H'4); 6.62 (s; H3), 6.55 (dd; J₁=9.2 Hz. J₂= 6.7 Hz, H12), 6.12 (d; J= 9.2 Hz, H13), 5.18 (d; J= 6.7 Hz, H1), 3.87 (s; 9, OCH₃), 3.84 (s; 6, OCH₃), 3.79 (s; 5, OCH₃), 3.63 (s; 4, OCH₃).

¹³C (CDCl₃), 400 MHz, Bruker Avance DPX400: δ(p.p.m.)= 190.2, (C8); 157.9, (C4); 156.7, (C6); 150.9, (C1'); 144.2, (C5); 136.7, (C12); 135.8, (C2); 129.3, (C3', C5'); 127.7, (C13); 123.4, (C4'); 120.5, (C7); 118.3, (C2', C6'); 109.4, (C3); 102.7, (C9); 69.5, (C9); 62.2, (C6, OCH₃); 61.4, (C5, OCH₃); 56.6, (C4, OCH₃); 53.3, (C9, OCH₃).

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.

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

	x	y	z	Uiso*/Ueq
C7	0.00563 (15)	0.77843 (19)	0.14866 (14)	0.0385 (4)
C6	−0.08759 (15)	0.7929 (2)	0.16777 (15)	0.0432 (5)
C5	−0.07709 (16)	0.8316 (2)	0.25884 (16)	0.0478 (5)
C4	0.02604 (17)	0.8594 (2)	0.33397 (16)	0.0484 (5)
C3	0.11862 (16)	0.8433 (2)	0.31717 (14)	0.0424 (5)
H3	0.1880	0.8598	0.3677	0.051*
C2	0.10964 (14)	0.80323 (18)	0.22696 (14)	0.0365 (4)
C1	0.21776 (14)	0.78348 (18)	0.21972 (13)	0.0351 (4)
H1	0.2786	0.7896	0.2858	0.042*
C12	0.22504 (15)	0.65380 (18)	0.17618 (15)	0.0388 (4)
H12	0.2681	0.5858	0.2148	0.047*
C13	0.16764 (15)	0.64135 (19)	0.08099 (15)	0.0417 (5)
H13	0.1728	0.5667	0.0482	0.050*
C9	0.09356 (15)	0.75240 (19)	0.02756 (13)	0.0386 (4)
O10	0.14043 (10)	0.88179 (12)	0.06203 (9)	0.0380 (3)
N11	0.22991 (11)	0.89065 (15)	0.15848 (10)	0.0348 (4)
C1'	0.33517 (14)	0.89093 (18)	0.15450 (13)	0.0362 (4)
C2'	0.42359 (15)	0.9407 (2)	0.23617 (15)	0.0459 (5)
H2'	0.4135	0.9686	0.2901	0.046 (6)*
C3'	0.52644 (17)	0.9491 (2)	0.23794 (18)	0.0572 (6)
H3'	0.5855	0.9818	0.2932	0.067 (7)*
C4'	0.54176 (18)	0.9092 (3)	0.15815 (19)	0.0653 (7)
H4'	0.6110	0.9155	0.1592	0.066 (7)*
C5'	0.4545 (2)	0.8600 (3)	0.07699 (19)	0.0658 (7)
H5'	0.4652	0.8326	0.0232	0.080 (8)*
C6'	0.35047 (17)	0.8505 (2)	0.07421 (15)	0.0507 (5)
H6'	0.2917	0.8172	0.0189	0.048 (6)*
O81	−0.09261 (12)	0.69348 (19)	−0.01466 (12)	0.0658 (5)
C61	−0.24770 (18)	0.8769 (2)	0.04003 (18)	0.0619 (6)
H61A	−0.3199	0.8514	−0.0075	0.074*
H61B	−0.2066	0.9103	0.0068	0.074*
H61C	−0.2540	0.9436	0.0819	0.074*
C51	−0.2104 (2)	0.7344 (3)	0.2982 (2)	0.0899 (11)
H51A	−0.2746	0.7547	0.3075	0.108*
H51B	−0.1546	0.6982	0.3576	0.108*
H51C	−0.2293	0.6719	0.2460	0.108*
C41	0.12584 (19)	0.9639 (3)	0.48911 (18)	0.0671 (7)
H41A	0.1171	0.9860	0.5469	0.081*
H41B	0.1369	1.0423	0.4597	0.081*
H41C	0.1885	0.9075	0.5067	0.081*
C91	0.0061 (2)	0.8511 (2)	−0.13090 (16)	0.0593 (6)
H91A	−0.0072	0.8362	−0.1977	0.071*
H91B	0.0466	0.9311	−0.1078	0.071*
H91C	−0.0630	0.8576	−0.1273	0.071*
C8	−0.00847 (15)	0.7393 (2)	0.04852 (15)	0.0427 (5)
O61	−0.19195 (10)	0.76589 (15)	0.09787 (11)	0.0539 (4)
O51	−0.16999 (12)	0.85037 (17)	0.27366 (13)	0.0636 (5)
O41	0.02894 (13)	0.89809 (19)	0.42060 (12)	0.0673 (5)
O91	0.06864 (12)	0.74409 (14)	−0.07090 (9)	0.0490 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C7	0.0309 (9)	0.0398 (10)	0.0434 (10)	0.0015 (8)	0.0149 (8)	0.0043 (8)
C6	0.0268 (9)	0.0438 (11)	0.0550 (12)	0.0002 (8)	0.0141 (9)	0.0101 (9)
C5	0.0331 (10)	0.0573 (13)	0.0597 (13)	0.0067 (9)	0.0262 (9)	0.0080 (10)
C4	0.0418 (11)	0.0592 (14)	0.0509 (12)	0.0060 (10)	0.0263 (10)	0.0018 (10)
C3	0.0324 (10)	0.0534 (12)	0.0416 (10)	0.0005 (9)	0.0165 (8)	0.0003 (9)
C2	0.0296 (9)	0.0400 (10)	0.0415 (10)	0.0023 (8)	0.0171 (8)	0.0036 (8)
C1	0.0255 (8)	0.0453 (10)	0.0334 (9)	0.0012 (8)	0.0119 (7)	0.0030 (8)
C12	0.0320 (9)	0.0370 (10)	0.0478 (11)	0.0037 (8)	0.0179 (8)	0.0068 (8)
C13	0.0391 (10)	0.0371 (10)	0.0491 (11)	0.0023 (8)	0.0193 (9)	−0.0020 (9)
C9	0.0338 (10)	0.0407 (11)	0.0355 (9)	−0.0010 (8)	0.0100 (8)	−0.0036 (8)
O10	0.0315 (7)	0.0381 (7)	0.0369 (7)	0.0007 (5)	0.0081 (5)	0.0029 (6)
N11	0.0270 (7)	0.0404 (8)	0.0338 (8)	0.0003 (7)	0.0104 (6)	−0.0006 (7)
C1'	0.0318 (9)	0.0361 (9)	0.0428 (10)	0.0033 (8)	0.0183 (8)	0.0047 (8)
C2'	0.0361 (10)	0.0517 (12)	0.0499 (11)	−0.0030 (9)	0.0188 (9)	−0.0048 (10)
C3'	0.0351 (11)	0.0654 (15)	0.0672 (15)	−0.0052 (10)	0.0188 (11)	0.0010 (12)
C4'	0.0364 (12)	0.0895 (19)	0.0785 (17)	0.0035 (12)	0.0330 (12)	0.0177 (15)
C5'	0.0580 (15)	0.093 (2)	0.0620 (15)	0.0077 (13)	0.0408 (13)	0.0062 (14)
C6'	0.0431 (11)	0.0697 (15)	0.0420 (11)	0.0024 (10)	0.0210 (10)	0.0040 (10)
O81	0.0414 (8)	0.0868 (12)	0.0588 (9)	−0.0174 (8)	0.0124 (7)	−0.0184 (9)
C61	0.0403 (12)	0.0710 (16)	0.0639 (15)	0.0120 (11)	0.0132 (10)	0.0121 (13)
C51	0.0595 (16)	0.123 (3)	0.110 (2)	0.0247 (17)	0.0585 (17)	0.054 (2)
C41	0.0571 (14)	0.0875 (19)	0.0608 (14)	0.0084 (14)	0.0294 (12)	−0.0169 (14)
C91	0.0566 (14)	0.0620 (15)	0.0394 (11)	−0.0034 (11)	0.0024 (10)	0.0065 (10)
C8	0.0306 (9)	0.0432 (11)	0.0466 (11)	−0.0017 (8)	0.0098 (8)	0.0002 (9)
O61	0.0269 (7)	0.0596 (9)	0.0640 (10)	−0.0024 (6)	0.0097 (6)	0.0122 (8)
O51	0.0397 (8)	0.0797 (12)	0.0832 (11)	0.0097 (8)	0.0376 (8)	0.0072 (9)
O41	0.0507 (9)	0.1044 (14)	0.0582 (10)	−0.0014 (9)	0.0345 (8)	−0.0161 (9)
O91	0.0521 (8)	0.0541 (9)	0.0346 (7)	0.0032 (7)	0.0132 (6)	−0.0022 (6)

Geometric parameters (Å, º)

C7—C2	1.409 (3)	C9—O10	1.460 (2)
C7—C6	1.417 (3)	C9—C8	1.548 (3)
C7—C8	1.499 (3)	O10—N11	1.4345 (18)
C6—O61	1.370 (2)	N11—C1'	1.448 (2)
C6—C5	1.382 (3)	C1'—C6'	1.383 (3)
C5—O51	1.381 (2)	C1'—C2'	1.386 (3)
C5—C4	1.388 (3)	C2'—C3'	1.379 (3)
C4—O41	1.355 (3)	C3'—C4'	1.375 (3)
C4—C3	1.390 (3)	C4'—C5'	1.373 (4)
C3—C2	1.380 (3)	C5'—C6'	1.390 (3)
C2—C1	1.524 (2)	O81—C8	1.214 (2)
C1—N11	1.490 (2)	C61—O61	1.430 (3)
C1—C12	1.502 (3)	C51—O51	1.420 (3)
C12—C13	1.311 (3)	C41—O41	1.432 (3)
C13—C9	1.495 (3)	C91—O91	1.437 (3)
C9—O91	1.381 (2)
C2—C7—C6	117.10 (17)	O10—C9—C13	114.29 (14)
C2—C7—C8	122.61 (17)	O91—C9—C8	113.48 (15)
C6—C7—C8	120.29 (17)	O10—C9—C8	106.83 (15)
O61—C6—C5	116.83 (18)	C13—C9—C8	105.52 (16)
O61—C6—C7	121.69 (19)	N11—O10—C9	117.48 (12)
C5—C6—C7	121.46 (17)	O10—N11—C1'	111.19 (13)
O51—C5—C6	119.92 (18)	O10—N11—C1	108.37 (13)
O51—C5—C4	119.6 (2)	C1'—N11—C1	113.88 (14)
C6—C5—C4	120.36 (18)	C6'—C1'—C2'	119.55 (17)
O41—C4—C5	116.60 (18)	C6'—C1'—N11	124.26 (17)
O41—C4—C3	124.40 (19)	C2'—C1'—N11	116.13 (16)
C5—C4—C3	118.98 (19)	C3'—C2'—C1'	120.4 (2)
C2—C3—C4	121.34 (18)	C4'—C3'—C2'	120.1 (2)
C3—C2—C7	120.71 (17)	C5'—C4'—C3'	119.8 (2)
C3—C2—C1	116.03 (16)	C4'—C5'—C6'	120.8 (2)
C7—C2—C1	123.23 (16)	C1'—C6'—C5'	119.4 (2)
N11—C1—C12	109.18 (14)	O81—C8—C7	124.18 (19)
N11—C1—C2	108.51 (14)	O81—C8—C9	118.70 (18)
C12—C1—C2	113.40 (15)	C7—C8—C9	117.04 (16)
C13—C12—C1	116.62 (17)	C6—O61—C61	113.65 (16)
C12—C13—C9	117.08 (17)	C5—O51—C51	113.99 (18)
O91—C9—O10	107.74 (15)	C4—O41—C41	117.98 (17)
O91—C9—C13	109.11 (16)	C9—O91—C91	115.76 (16)
C2—C7—C6—O61	−177.24 (17)	C12—C1—N11—O10	62.14 (17)
C8—C7—C6—O61	3.2 (3)	C2—C1—N11—O10	−61.90 (17)
C2—C7—C6—C5	0.9 (3)	C12—C1—N11—C1'	−62.15 (18)
C8—C7—C6—C5	−178.60 (19)	C2—C1—N11—C1'	173.80 (14)
O61—C6—C5—O51	−4.6 (3)	O10—N11—C1'—C6'	−17.4 (2)
C7—C6—C5—O51	177.10 (19)	C1—N11—C1'—C6'	105.3 (2)
O61—C6—C5—C4	179.33 (19)	O10—N11—C1'—C2'	159.78 (16)
C7—C6—C5—C4	1.1 (3)	C1—N11—C1'—C2'	−77.5 (2)
O51—C5—C4—O41	3.2 (3)	C6'—C1'—C2'—C3'	−0.5 (3)
C6—C5—C4—O41	179.3 (2)	N11—C1'—C2'—C3'	−177.83 (19)
O51—C5—C4—C3	−178.34 (19)	C1'—C2'—C3'—C4'	0.6 (3)
C6—C5—C4—C3	−2.3 (3)	C2'—C3'—C4'—C5'	−0.5 (4)
O41—C4—C3—C2	179.8 (2)	C3'—C4'—C5'—C6'	0.3 (4)
C5—C4—C3—C2	1.5 (3)	C2'—C1'—C6'—C5'	0.3 (3)
C4—C3—C2—C7	0.5 (3)	N11—C1'—C6'—C5'	177.4 (2)
C4—C3—C2—C1	−177.34 (18)	C4'—C5'—C6'—C1'	−0.2 (4)
C6—C7—C2—C3	−1.7 (3)	C2—C7—C8—O81	165.3 (2)
C8—C7—C2—C3	177.80 (18)	C6—C7—C8—O81	−15.2 (3)
C6—C7—C2—C1	175.99 (17)	C2—C7—C8—C9	−11.4 (3)
C8—C7—C2—C1	−4.5 (3)	C6—C7—C8—C9	168.09 (17)
C3—C2—C1—N11	−108.72 (18)	O91—C9—C8—O81	17.2 (3)
C7—C2—C1—N11	73.5 (2)	O10—C9—C8—O81	135.80 (19)
C3—C2—C1—C12	129.79 (18)	C13—C9—C8—O81	−102.2 (2)
C7—C2—C1—C12	−48.0 (2)	O91—C9—C8—C7	−165.87 (16)
N11—C1—C12—C13	−45.9 (2)	O10—C9—C8—C7	−47.3 (2)
C2—C1—C12—C13	75.2 (2)	C13—C9—C8—C7	74.7 (2)
C1—C12—C13—C9	−5.4 (3)	C5—C6—O61—C61	90.1 (2)
C12—C13—C9—O91	160.46 (17)	C7—C6—O61—C61	−91.7 (2)
C12—C13—C9—O10	39.8 (2)	C6—C5—O51—C51	85.4 (3)
C12—C13—C9—C8	−77.3 (2)	C4—C5—O51—C51	−98.5 (3)
O91—C9—O10—N11	−141.62 (14)	C5—C4—O41—C41	−161.8 (2)
C13—C9—O10—N11	−20.2 (2)	C3—C4—O41—C41	19.9 (3)
C8—C9—O10—N11	96.12 (16)	O10—C9—O91—C91	−49.9 (2)
C9—O10—N11—C1'	96.91 (17)	C13—C9—O91—C91	−174.48 (16)
C9—O10—N11—C1	−28.98 (18)	C8—C9—O91—C91	68.2 (2)