1-(12-Benzoyl-10-oxa-12-aza­tetra­cyclo­[6.3.1.0^2,7.0^9,11]­dodeca-2,4,6-trien-1-yl)­ethan-1-one

The title compound, C₁₉H₁₅NO₃, is non-planar with a dihedral angle between the benzonorborna­diene benzene ring and the benzoyl aromatic ring of 28.7 (1)°. In the crystal structure, there are three intermolecular C—H...O bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 8.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.99
         From the CIF: _reflns_number_total               2118
         Count of symmetry unique reflns         2118
         Completeness (_total/calc)            100.00%
         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

The most general preparative method for 7-azobenzonorbornadiene (1,4-dihydronaphthalene-1,4-imine) involves benzyne cycloadditions to suitable conjugated dienes (Wolthuis & De Boer, 1965; Wolthuis et al., 1966). 7-Azobenzonorbornadiene itself is of great synthetic interest because of its ready conversion to other types of compounds (Carpino & Barr, 1966; Kaupp et al., 1970; Swenton et al., 1974; Motyka, 1985). In this class of compounds, the configurations of the R groups bound to the nitrogen are changable; however, the exact configuration can be indentified by spectroscopic studies, as shown in the literature (Quin et al., 1986; Davies et al., 1992).

In our synthetic strategy, based on the Diels–Alder cycloaddition of benzyne (1) to N-benzoyl-2-acetylpyrrole, (2), we obtained the novel 1,4-iminonaphthalene derivative (3). NMR data of (3) indicated that the molecule exists as a single isomer. However, the configuration of the benzoyl group bound to the N atom could not be determined by NMR spectroscopy. Epoxidation of N-benzoyl-1,4-iminonaphthalene, (3), with m-chloroperbenzoic acid resulted in the formation of only one isomer, namely the exo-epoxide (4), whose structure analysis is reported here.

The N1—C12 bond length of 1.386 (3) Å is shorter than typical for a single bond due to the influence of the neighbouring C12═O2 bond [1.220 (3) Å]. The average value of the O1—C8 and O1—C9 distances is 1.360 (4) Å; the corresponding value in a related structure is 1.455 (2) Å (Usman et al., 2002). The C8—C9 distance of 1.452 (3) Å and the average value of 114.21 (19)° for the O1—C8—C7 and O1—C9—C10 angles are almost in agreement with the values of 1.426 (16) Å and 112.6 (10)°, respectively, in the same structure. The remaining bond lengths and angles in the title compound are normal and are in agreement with those observed in similar compounds (Mague et al.,1993; Jones et al., 1992).

The five-membered rings N1/C7/C6/C1/C10 and N1/C7/C8/C9/C10 exhibit envelope conformations on atom N1. The puckering parameters (Cremer & Pople, 1975) for these rings are Q₂ = 0.553 (2) Å and ϕ₂ = 0.7 (3)°, and Q₂ = 0.536 (2) Å and ϕ₂ = 178.6 (3)°, respectively.

Plane A (C1–C7/C10) is almost planar [maximum deviations at C3, C6 and C7 are −0.024 (3), 0.031 (2) and −0.024 (2) Å, respectively]. The dihedral angle between plane A and plane B (C13–C18) is 28.2 (1)°, and that between plane A and plane C (C–C10) is 73 (1)°. The epoxy ring, formed by atoms O1, C8 and C9, is aligned parallel to plane A, but pointing in the opposite direction.

Hydrogen-bonding contacts are summarized in Table 2. The crystal structure is stabilized by three C—H···O intermolecular hydrogen bonds in addition to van der Waals forces (Fig. 2).

S2. Experimental

A solution of 1.74 mmol (500 mg) N-benzoyl-1,4-iminonaphthalene, (3), and 2.09 mmol (362 mg) of m-chloroperbenzoic acid in 30 ml of CH₂Cl₂ was stirred for 20 h at room temperature in the presence of solid NaHCO₃ (1 g). The reaction mixture was extracted with 10% NaHSO₃ (2 × 50 ml) then with 10% NaHCO₃ (2 × 20 ml). The organic layer was dried over MgSO₄. The solvent was then evaporated and the residue recrystallized from 1:2 CHCl₃–hexane, m.p. 481–484 K, giving colourless crystals in 78% (416 mg) yield. ¹H NMR (200 MHz, CDCl₃): δ 7.68–7.12 (m, aromatic, 9H), 5.09 (s, bridgehead, 1H), 3.97 (d, J = 3.5 Hz, 1H), 3.39 (d, J = 3.5 Hz, 1H), 2.42 (s, methyl, 3H). ¹³C NMR (50 MHz, CDCl₃): δ 201.20, 175.78, 145.79, 145.33, 136.07, 132.97, 130.47, 130.16, 129.64, 129.57, 123.49, 123.02, 82.51, 67.91, 58.54, 54.52, 29.77. IR (KBr) cm⁻¹: 3027, 2931, 2858, 1708, 1631, 1581, 1457, 1427, 1373, 1276, 1130, 1064, 1025, 944, 887, 848, 755, 698.

S3. Refinement

The H atoms were placed in geometriclly idealized positions and constrained to ride on their parent atoms.

Computing details

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound, showing the labelling of the non-H atoms. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view of the crystal packing. Short hydrogen-bond contacts are indicated by dashed lines.

1-(12-benzoyl-10-oxa-12-azatetracyclo[6.3.1.0^2,7.0^9,11] dodeca-2,4,6-trien-1-yl)ethan-1-one

Crystal data

C19H15NO3	F(000) = 640
Mr = 305.32	Dx = 1.326 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 74 reflections
a = 7.829 (1) Å	θ = 2.9–15.0°
b = 13.874 (1) Å	µ = 0.09 mm^−1
c = 14.079 (1) Å	T = 298 K
V = 1529.3 (2) Å^3	Block, colourless
Z = 4	0.55 × 0.50 × 0.40 mm

Data collection

Siemens P4 diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.1°
Graphite monochromator	h = −10→10
profile data from ω scans	k = −18→18
4236 measured reflections	l = −18→18
2118 independent reflections	3 standard reflections every 100 reflections
1622 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.039	Only H-atom coordinates refined
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.0258P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
2118 reflections	Δρmax = 0.16 e Å^−3
254 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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
O1	0.0696 (2)	0.54500 (13)	0.29867 (11)	0.0466 (5)
O2	0.1501 (2)	0.75829 (13)	0.25304 (14)	0.0496 (6)
O3	0.4341 (2)	0.61882 (15)	0.13589 (16)	0.0622 (7)
N1	−0.0147 (2)	0.65772 (13)	0.16517 (13)	0.0311 (5)
C1	0.0556 (3)	0.55410 (15)	0.04436 (15)	0.0344 (7)
C2	0.1223 (4)	0.5242 (2)	−0.04162 (18)	0.0462 (8)
C3	0.0123 (5)	0.4785 (2)	−0.10461 (19)	0.0560 (10)
C4	−0.1583 (5)	0.4637 (2)	−0.0821 (2)	0.0565 (10)
C5	−0.2241 (4)	0.4948 (2)	0.0043 (2)	0.0460 (8)
C6	−0.1165 (3)	0.53988 (15)	0.06707 (16)	0.0341 (6)
C7	−0.1385 (3)	0.57656 (16)	0.16771 (17)	0.0339 (7)
C8	−0.0412 (3)	0.50225 (18)	0.22773 (17)	0.0400 (7)
C9	0.1376 (3)	0.51918 (17)	0.20596 (17)	0.0373 (7)
C10	0.1357 (3)	0.60134 (16)	0.13219 (15)	0.0327 (6)
C12	0.0093 (3)	0.72405 (16)	0.23758 (16)	0.0342 (6)
C13	−0.1456 (3)	0.75679 (16)	0.29036 (17)	0.0346 (6)
C14	−0.3033 (3)	0.76940 (19)	0.2479 (2)	0.0429 (7)
C15	−0.4419 (4)	0.7999 (2)	0.3016 (2)	0.0528 (9)
C16	−0.4211 (4)	0.8172 (2)	0.3973 (2)	0.0571 (10)
C17	−0.2644 (4)	0.8070 (2)	0.4392 (2)	0.0549 (10)
C18	−0.1244 (4)	0.77794 (19)	0.38645 (18)	0.0436 (8)
C19	0.3002 (3)	0.65500 (18)	0.11263 (17)	0.0397 (7)
C20	0.2912 (4)	0.7467 (3)	0.0562 (2)	0.0591 (10)
H2	0.243 (5)	0.530 (2)	−0.052 (2)	0.0800*
H3	0.055 (5)	0.461 (2)	−0.167 (2)	0.0800*
H4	−0.231 (5)	0.433 (3)	−0.132 (3)	0.0800*
H5	−0.355 (5)	0.490 (2)	0.025 (2)	0.0800*
H7	−0.256 (5)	0.592 (2)	0.189 (2)	0.0800*
H8	−0.094 (5)	0.440 (3)	0.243 (2)	0.0800*
H9	0.228 (4)	0.473 (3)	0.203 (2)	0.0800*
H14	−0.322 (4)	0.758 (2)	0.181 (2)	0.0800*
H15	−0.551 (5)	0.817 (2)	0.265 (2)	0.0800*
H16	−0.517 (5)	0.839 (2)	0.433 (2)	0.0800*
H17	−0.245 (5)	0.821 (2)	0.506 (3)	0.0800*
H18	−0.008 (4)	0.774 (3)	0.414 (2)	0.0800*
H20A	0.181 (5)	0.768 (3)	0.045 (2)	0.0800*
H20B	0.341 (5)	0.736 (3)	0.003 (3)	0.0800*
H20C	0.383 (5)	0.796 (2)	0.082 (2)	0.0800*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0522 (11)	0.0525 (9)	0.0352 (8)	0.0041 (9)	−0.0024 (8)	0.0025 (8)
O2	0.0308 (8)	0.0524 (10)	0.0655 (12)	−0.0052 (8)	−0.0019 (9)	−0.0158 (10)
O3	0.0269 (9)	0.0694 (13)	0.0902 (15)	0.0032 (10)	−0.0029 (10)	−0.0055 (12)
N1	0.0225 (8)	0.0311 (9)	0.0397 (9)	−0.0005 (8)	0.0013 (8)	−0.0003 (8)
C1	0.0341 (11)	0.0310 (11)	0.0380 (12)	0.0015 (10)	−0.0024 (10)	0.0014 (9)
C2	0.0518 (16)	0.0461 (14)	0.0407 (13)	0.0024 (13)	0.0055 (13)	−0.0024 (11)
C3	0.076 (2)	0.0554 (16)	0.0365 (13)	−0.0025 (16)	0.0028 (15)	−0.0050 (13)
C4	0.073 (2)	0.0508 (15)	0.0458 (15)	−0.0095 (16)	−0.0168 (15)	−0.0068 (13)
C5	0.0473 (16)	0.0392 (12)	0.0516 (15)	−0.0106 (13)	−0.0091 (13)	0.0016 (12)
C6	0.0338 (12)	0.0291 (10)	0.0395 (11)	−0.0013 (10)	−0.0018 (10)	0.0003 (9)
C7	0.0289 (11)	0.0323 (11)	0.0406 (12)	−0.0053 (10)	0.0031 (11)	0.0002 (9)
C8	0.0443 (14)	0.0363 (11)	0.0393 (13)	−0.0022 (11)	0.0027 (11)	0.0052 (10)
C9	0.0371 (12)	0.0378 (12)	0.0371 (11)	0.0070 (11)	−0.0008 (11)	0.0013 (10)
C10	0.0268 (10)	0.0345 (11)	0.0367 (11)	0.0022 (9)	−0.0023 (10)	0.0008 (10)
C12	0.0275 (10)	0.0322 (11)	0.0428 (12)	0.0006 (9)	−0.0027 (10)	−0.0005 (10)
C13	0.0314 (11)	0.0316 (10)	0.0407 (12)	−0.0041 (10)	0.0020 (10)	−0.0014 (10)
C14	0.0325 (11)	0.0418 (12)	0.0543 (15)	−0.0008 (10)	−0.0031 (12)	−0.0073 (13)
C15	0.0327 (13)	0.0477 (14)	0.078 (2)	0.0022 (12)	0.0060 (15)	−0.0056 (14)
C16	0.0526 (17)	0.0448 (14)	0.074 (2)	0.0009 (14)	0.0262 (17)	−0.0079 (14)
C17	0.064 (2)	0.0501 (15)	0.0505 (16)	−0.0044 (15)	0.0143 (15)	−0.0050 (13)
C18	0.0436 (14)	0.0411 (12)	0.0462 (13)	−0.0030 (12)	0.0023 (12)	−0.0008 (11)
C19	0.0324 (12)	0.0461 (13)	0.0407 (13)	−0.0026 (11)	0.0018 (11)	−0.0057 (11)
C20	0.0481 (16)	0.0652 (19)	0.0640 (19)	−0.0174 (16)	0.0103 (16)	0.0128 (16)

Geometric parameters (Å, º)

O1—C8	1.450 (3)	C13—C18	1.394 (3)
O1—C9	1.454 (3)	C14—C15	1.389 (4)
O2—C12	1.220 (3)	C15—C16	1.378 (4)
O3—C19	1.208 (3)	C16—C17	1.369 (4)
N1—C7	1.486 (3)	C17—C18	1.384 (4)
N1—C10	1.488 (3)	C19—C20	1.502 (5)
N1—C12	1.386 (3)	C2—H2	0.96 (4)
C1—C2	1.382 (3)	C3—H3	0.97 (3)
C1—C6	1.399 (3)	C4—H4	1.00 (4)
C1—C10	1.534 (3)	C5—H5	1.07 (4)
C2—C3	1.389 (4)	C7—H7	0.99 (4)
C3—C4	1.388 (5)	C8—H8	0.98 (4)
C4—C5	1.390 (4)	C9—H9	0.96 (4)
C5—C6	1.372 (4)	C14—H14	0.97 (3)
C6—C7	1.515 (3)	C15—H15	1.03 (4)
C7—C8	1.535 (3)	C16—H16	0.95 (4)
C8—C9	1.452 (3)	C17—H17	0.97 (4)
C9—C10	1.542 (3)	C18—H18	0.99 (3)
C10—C19	1.513 (3)	C20—H20A	0.93 (4)
C12—C13	1.493 (3)	C20—H20B	0.86 (4)
C13—C14	1.383 (3)	C20—H20C	1.06 (3)
O1···O2	3.093 (3)	C13···H9^iv	3.07 (4)
O1···N1	2.533 (2)	C13···H4^iii	3.01 (4)
O1···C12	2.671 (3)	C13···H7	2.83 (3)
O1···C13	3.389 (3)	C14···H9^iv	2.97 (4)
O2···C9	3.384 (3)	C14···H7	2.62 (3)
O2···C15^i	3.317 (4)	C15···H9^iv	2.93 (4)
O2···O1	3.093 (3)	C16···H9^iv	2.99 (4)
O2···C20	2.988 (3)	C16···H18^xi	3.02 (3)
O2···C19	2.710 (3)	C17···H18^xi	3.03 (3)
O3···C14^i	3.328 (3)	C17···H9^iv	3.06 (4)
O1···H2^ii	2.77 (3)	C18···H9^iv	3.09 (4)
O1···H4^iii	2.84 (4)	C19···H2	2.93 (3)
O2···H18	2.59 (3)	H2···C19	2.93 (3)
O2···H8^iv	2.56 (4)	H2···O1^xii	2.77 (3)
O2···H15^i	2.48 (4)	H3···C9^xii	3.01 (4)
O3···H5^i	2.89 (3)	H4···O1^vi	2.84 (4)
O3···H7^i	2.57 (4)	H4···C7^vi	3.00 (4)
O3···H9	2.75 (4)	H4···C8^vi	2.81 (4)
O3···H14^i	2.79 (3)	H4···C13^vi	3.01 (4)
N1···O1	2.533 (2)	H4···H7^vi	2.55 (5)
N1···H14	2.79 (3)	H5···O3^viii	2.89 (3)
N1···H20A	2.75 (4)	H5···H16^x	2.40 (4)
C2···C17^v	3.521 (4)	H7···O3^viii	2.57 (4)
C4···C8^vi	3.595 (4)	H7···C13	2.83 (3)
C6···C20^vii	3.507 (4)	H7···C14	2.62 (3)
C7···C14	3.178 (3)	H7···H14	2.36 (4)
C8···C4^iii	3.595 (4)	H7···H4^iii	2.55 (5)
C9···O2	3.384 (3)	H8···O2^v	2.56 (4)
C9···C18^v	3.592 (4)	H8···C12^v	3.08 (4)
C12···C20	3.390 (4)	H9···O3	2.75 (4)
C12···O1	2.671 (3)	H9···C13^v	3.07 (4)
C13···O1	3.389 (3)	H9···C14^v	2.97 (4)
C14···C7	3.178 (3)	H9···C15^v	2.93 (4)
C14···O3^viii	3.328 (3)	H9···C16^v	2.99 (4)
C15···O2^viii	3.317 (4)	H9···C17^v	3.06 (4)
C17···C2^iv	3.521 (4)	H9···C18^v	3.09 (4)
C18···C9^iv	3.592 (4)	H14···O3^viii	2.79 (3)
C19···O2	2.710 (3)	H14···N1	2.79 (3)
C20···C6^ix	3.507 (4)	H14···C7	2.90 (3)
C20···O2	2.988 (3)	H14···H7	2.36 (4)
C20···C12	3.390 (4)	H15···O2^viii	2.48 (4)
C1···H20C^vii	3.05 (3)	H16···C5^xiii	3.09 (3)
C2···H17^v	3.02 (3)	H16···H5^xiii	2.40 (4)
C5···H16^x	3.09 (3)	H17···C2^iv	3.02 (3)
C6···H20C^vii	3.10 (3)	H18···O2	2.59 (3)
C7···H4^iii	3.00 (4)	H18···C16^xiv	3.02 (3)
C7···H14	2.90 (3)	H18···C17^xiv	3.03 (3)
C8···H4^iii	2.81 (4)	H20A···N1	2.75 (4)
C9···H3^ii	3.01 (4)	H20A···C12	3.09 (3)
C12···H8^iv	3.08 (4)	H20C···C1^ix	3.05 (3)
C12···H20A	3.09 (3)	H20C···C6^ix	3.10 (3)
C8—O1—C9	60.00 (15)	C16—C17—C18	120.6 (3)
C7—N1—C10	97.20 (16)	C13—C18—C17	119.2 (3)
C7—N1—C12	125.01 (18)	O3—C19—C10	119.0 (2)
C10—N1—C12	118.12 (17)	O3—C19—C20	122.4 (2)
C2—C1—C6	121.5 (2)	C10—C19—C20	118.2 (2)
C2—C1—C10	132.8 (2)	C1—C2—H2	118.7 (17)
C6—C1—C10	105.66 (18)	C3—C2—H2	123.5 (17)
C1—C2—C3	117.5 (3)	C2—C3—H3	119 (2)
C2—C3—C4	121.2 (3)	C4—C3—H3	120 (2)
C3—C4—C5	120.7 (3)	C3—C4—H4	117 (2)
C4—C5—C6	118.5 (3)	C5—C4—H4	122 (2)
C1—C6—C5	120.6 (2)	C4—C5—H5	125.1 (16)
C1—C6—C7	106.01 (19)	C6—C5—H5	116.2 (16)
C5—C6—C7	133.3 (2)	N1—C7—H7	116.7 (17)
N1—C7—C6	99.08 (18)	C6—C7—H7	117.4 (17)
N1—C7—C8	101.45 (18)	C8—C7—H7	116.1 (16)
C6—C7—C8	103.46 (18)	O1—C8—H8	117.5 (18)
O1—C8—C7	113.66 (19)	C7—C8—H8	120 (2)
O1—C8—C9	60.16 (15)	C9—C8—H8	126 (2)
C7—C8—C9	104.7 (2)	O1—C9—H9	118.4 (17)
O1—C9—C8	59.84 (15)	C8—C9—H9	128 (2)
O1—C9—C10	114.76 (19)	C10—C9—H9	118 (2)
C8—C9—C10	104.62 (19)	C13—C14—H14	122.4 (19)
N1—C10—C1	98.78 (17)	C15—C14—H14	117.5 (19)
N1—C10—C9	100.72 (17)	C14—C15—H15	116.6 (18)
N1—C10—C19	118.15 (19)	C16—C15—H15	123.3 (17)
C1—C10—C9	103.36 (18)	C15—C16—H16	119 (2)
C1—C10—C19	114.31 (18)	C17—C16—H16	121 (2)
C9—C10—C19	118.56 (19)	C16—C17—H17	122 (2)
O2—C12—N1	120.8 (2)	C18—C17—H17	117 (2)
O2—C12—C13	121.8 (2)	C13—C18—H18	118.5 (17)
N1—C12—C13	117.25 (19)	C17—C18—H18	122.3 (18)
C12—C13—C14	123.3 (2)	C19—C20—H20A	114 (2)
C12—C13—C18	116.8 (2)	C19—C20—H20B	107 (3)
C14—C13—C18	119.9 (2)	C19—C20—H20C	109.6 (16)
C13—C14—C15	120.1 (3)	H20A—C20—H20B	109 (3)
C14—C15—C16	119.5 (3)	H20A—C20—H20C	119 (3)
C15—C16—C17	120.6 (3)	H20B—C20—H20C	96 (3)
C9—O1—C8—C7	−93.9 (2)	C5—C6—C7—N1	−150.0 (3)
C8—O1—C9—C10	93.1 (2)	C5—C6—C7—C8	105.9 (3)
C12—N1—C7—C6	174.22 (19)	C1—C6—C7—N1	34.3 (2)
C10—N1—C7—C6	−53.84 (18)	C6—C7—C8—C9	70.7 (2)
C10—N1—C7—C8	51.99 (19)	C6—C7—C8—O1	134.12 (19)
C7—N1—C10—C9	−52.51 (19)	N1—C7—C8—O1	31.8 (2)
C7—N1—C10—C19	176.70 (19)	N1—C7—C8—C9	−31.7 (2)
C12—N1—C10—C1	−170.70 (18)	C7—C8—C9—O1	109.1 (2)
C12—N1—C10—C9	83.8 (2)	C7—C8—C9—C10	−1.3 (2)
C12—N1—C10—C19	−47.0 (3)	O1—C8—C9—C10	−110.43 (19)
C7—N1—C12—O2	146.4 (2)	O1—C9—C10—N1	−29.4 (2)
C7—N1—C12—C13	−38.0 (3)	O1—C9—C10—C1	−131.24 (19)
C10—N1—C12—O2	23.2 (3)	O1—C9—C10—C19	101.1 (2)
C10—N1—C12—C13	−161.19 (19)	C8—C9—C10—N1	33.7 (2)
C7—N1—C10—C1	52.99 (18)	C8—C9—C10—C1	−68.1 (2)
C12—N1—C7—C8	−80.0 (2)	C8—C9—C10—C19	164.3 (2)
C10—C1—C6—C5	−177.3 (2)	N1—C10—C19—C20	−45.9 (3)
C10—C1—C6—C7	−0.9 (2)	C1—C10—C19—O3	−104.3 (3)
C2—C1—C6—C7	176.9 (2)	N1—C10—C19—O3	140.2 (2)
C6—C1—C2—C3	−0.6 (4)	C9—C10—C19—C20	−168.0 (2)
C10—C1—C2—C3	176.6 (2)	C1—C10—C19—C20	69.7 (3)
C2—C1—C6—C5	0.5 (3)	C9—C10—C19—O3	18.1 (3)
C6—C1—C10—C9	70.6 (2)	O2—C12—C13—C18	−37.8 (3)
C6—C1—C10—C19	−159.13 (19)	N1—C12—C13—C14	−35.4 (3)
C2—C1—C10—C9	−106.9 (3)	N1—C12—C13—C18	146.7 (2)
C2—C1—C10—C19	23.4 (4)	O2—C12—C13—C14	140.2 (3)
C2—C1—C10—N1	149.8 (3)	C12—C13—C14—C15	179.9 (2)
C6—C1—C10—N1	−32.7 (2)	C18—C13—C14—C15	−2.2 (4)
C1—C2—C3—C4	0.2 (4)	C12—C13—C18—C17	−178.9 (2)
C2—C3—C4—C5	0.3 (4)	C14—C13—C18—C17	3.1 (4)
C3—C4—C5—C6	−0.4 (4)	C13—C14—C15—C16	−0.2 (4)
C4—C5—C6—C1	0.0 (4)	C14—C15—C16—C17	1.7 (4)
C4—C5—C6—C7	−175.2 (2)	C15—C16—C17—C18	−0.8 (4)
C1—C6—C7—C8	−69.9 (2)	C16—C17—C18—C13	−1.6 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, −y+1, z+1/2; (iii) −x−1/2, −y+1, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x, y−1/2, −z+1/2; (vi) −x−1/2, −y+1, z−1/2; (vii) x−1/2, −y+3/2, −z; (viii) x−1, y, z; (ix) x+1/2, −y+3/2, −z; (x) −x−1, y−1/2, −z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) −x+1/2, −y+1, z−1/2; (xiii) −x−1, y+1/2, −z+1/2; (xiv) x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3^viii	0.99 (4)	2.57 (4)	3.427 (3)	145 (2)
C8—H8···O2^v	0.98 (4)	2.56 (4)	3.501 (3)	161 (3)
C15—H15···O2^viii	1.03 (4)	2.48 (4)	3.317 (4)	138 (2)

Symmetry codes: (v) −x, y−1/2, −z+1/2; (viii) x−1, y, z.