A benzopyran derivative substituted at position 3

In (E)-3-{[(di­phenoxy­phospho­ryl)­methyl­hydrazono]­methyl}-4H-1-benzo­pyran-4-one, C₂₃H₁₉N₂O₅P, the benzo­pyran–methyl­hydrazone moiety is planar and the two phenoxy phenyl rings are inclined at angles of 21.29 (6) and 89.33 (5)°. Weak C—H...O and C—H...N intramolecular interactions exert some influence on the planarity and orientation of that moiety.

S1. Comment

This paper is a part of our X-ray studies of a group of benzopyran derivatives substituted with phosphorohydrazide at position 3 (Rybarczyk et al., 1999; Rybarczyk-Pirek et al., 2002). These compounds, which are derivatives of biologically active chromones, are of interest because of their expected anticancer activity, by analogy with other chromones (Gabor, 1988; Valenti et al., 1996). The present X-ray investigation of the title benzopyran derivative, (I), was undertaken to obtain structural information regarding the details of the molecular conformation. We were also interested in the weak interactions in the crystal structure. \sch

The planarity of the pyranoid ring in (I) reveals its aromatic character; the maximum deviation from the least-squares plane (Nardelli, 1996) is 0.016 (2) Å for atom C69. On the other hand, the presence of heteroatom O61 in this cyclic system, as well as the oxo substituent at position 4, significantly modifies the geometric parameters within the ring. The C—C bond distances vary from 1.340 (3) to 1.465 (3) Å, in comparison with the typical aromatic bond length of 1.384 (13) Å (Allen et al., 1987). Moreover, the values of the bond angles within the heterocyclic ring vary from 114.5 (2) to 125.9 (2)° (Table 1).

Fused benzene and pyranoid rings form the benzopyran system, which can be described as planar, with a dihedral angle between the best planes of the rings of 1.21 (6)°.

The hydrazone group (atoms C5, N4 and N3) lies in almost the same plane as the benzopyran moiety. The dihedral angle between the hydrazone and benzopyran least-squares planes is 5.0 (1)°. This coplanar arrangement of the main part of the molecule provides π-conjugation along the C63—C5—N4—N3 bonds and induces planar geometry around atom N3. In addition, the P1—N3 bond length is much closer to the standard P—N_planar distance of 1.65 (2) Å than to the P—N_pyramidal distance of 1.683 (5) Å (Allen et al., 1987).

The C_methyl and P atoms do not deviate much from the hydrazone best plane [0.030 (3) Å for atom C31 and 0.090 (1) Å for atom P1], and they are positioned on opposite sides of the plane. The normal to the hydrazone plane forms an angle of 81.4 (1)° with the P1—O2 bond. As a result, the central P1/N3(C31)/N4/C5/C63 chain of atoms can be regarded as planar.

The geometric parameters around the four-coordinate P atom indicate a slight deformation of the ideal tetrahedron towards a trigonal pyramid, caused by the different substituents and bond types. In particular, the P1═O2 double bond is the shortest and this has an influence on the bond angles in the P environment, which are significantly different from the ideal value of 109.5°.

Even though the majority of the atoms of the molecule lie in nearly the same plane, the tetrahedral geometry of the central phosphonate system results in the overall non-planar molecular conformation. The two phenoxy groups attached to atom P1 are inclined towards the benzopyran-hydrazone moiety; he angles between these rings and the main plane are 21.29 (6)° for the C12—C17 ring and 89.33 (5)° for the C22—C27 ring.

The coplanar arrangement of the main part of the molecule of (I) is additionally stabilized by the availability of acceptors in weak intramolecular contacts, of the non-conventional hydrogen-bonding type, with C—H donors. Some H···O and H···N distances shorter than the sum of the van der Waals radii are observed. The geometry of these weak hydrogen bonds is given in Table 2.

S2. Experimental

The title compound was obtained by the reaction of equimolar amounts of 4-oxo-4H-benzopyran-3-carboxyaldehyde (0.87 g, 0.005 mol) and N¹-diphenyloxyphosphonate-N¹-methylhydrazide (1.38 g) in anhydrous methanol solution (see reaction Scheme). After 24 h, the product was precipitated from the reaction solution (m.p. 393–395 K). Crystals of (I) suitable for X-ray analysis were obtained by recrystallization from methanol.

S3. Refinement

H atoms in benzenoid rings were constrained to their parent C atoms by a rigid body model, using the AFIX 43 instruction in SHELXL97 (Sheldrick, 1997). The remaining H atoms were freely refined.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1996).

Figures

Fig. 1. A view of the molecule of (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii.

(E)-3-{[(diphenyloxyphosphoryl)methylhydrazono]methyl}-4H-1-benzopyran-4-one

Crystal data

C23H19N2O5P	F(000) = 904
Mr = 434.37	Dx = 1.385 Mg m^−3 Dm = 1.378 Mg m^−3 Dm measured by flotation in a solution of KI and KBr in water
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.312 (2) Å	θ = 21.3–23.8°
b = 10.611 (1) Å	µ = 0.17 mm^−1
c = 23.595 (2) Å	T = 293 K
β = 90.76 (1)°	Prism, colourless
V = 2082.8 (5) Å^3	0.6 × 0.5 × 0.4 mm
Z = 4

Data collection

Rigaku AFC-5S diffractometer	2746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 3.5°
ω scans	h = −9→9
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = 0→12
Tmin = 0.915, Tmax = 0.944	l = 0→28
3738 measured reflections	3 standard reflections every 150 reflections
3648 independent reflections	intensity decay: <2%

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	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0798P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
3648 reflections	Δρmax = 0.28 e Å^−3
301 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Special details

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
P1	0.22022 (6)	0.36544 (5)	0.18452 (2)	0.0514 (2)
O2	0.25073 (18)	0.42753 (14)	0.23831 (6)	0.0654 (4)
N3	0.33831 (19)	0.24397 (15)	0.17406 (7)	0.0543 (4)
C31	0.4785 (3)	0.2169 (3)	0.20950 (11)	0.0658 (6)
N4	0.29932 (18)	0.16982 (15)	0.12761 (7)	0.0525 (4)
C5	0.3904 (2)	0.07810 (18)	0.11550 (8)	0.0503 (5)
O61	0.17005 (17)	−0.06544 (14)	−0.00660 (6)	0.0646 (4)
C62	0.2186 (2)	0.0101 (2)	0.03608 (9)	0.0561 (5)
H62	0.145 (3)	0.077 (2)	0.0397 (9)	0.072 (7)*
C63	0.3510 (2)	−0.00580 (17)	0.06826 (8)	0.0472 (4)
C64	0.4587 (2)	−0.11072 (18)	0.05635 (9)	0.0543 (5)
O641	0.58513 (19)	−0.12694 (15)	0.08232 (8)	0.0838 (5)
C65	0.4924 (3)	−0.2997 (2)	−0.00597 (12)	0.0748 (7)
H65	0.5881	−0.3194	0.0128	0.090*
C66	0.4379 (4)	−0.3747 (2)	−0.04955 (12)	0.0866 (8)
H66	0.4982	−0.4439	−0.0607	0.104*
C67	0.2949 (4)	−0.3482 (3)	−0.07680 (12)	0.0878 (8)
H67	0.2583	−0.4004	−0.1059	0.105*
C68	0.2065 (3)	−0.2459 (2)	−0.06157 (10)	0.0785 (7)
H68	0.1093	−0.2284	−0.0798	0.094*
C69	0.2629 (3)	−0.16894 (19)	−0.01875 (9)	0.0565 (5)
C70	0.4040 (2)	−0.19352 (18)	0.01031 (9)	0.0548 (5)
O11	0.04154 (15)	0.31704 (12)	0.17435 (5)	0.0530 (4)
C12	−0.0294 (2)	0.2327 (2)	0.21271 (8)	0.0544 (5)
C13	−0.0638 (3)	0.1127 (2)	0.19307 (11)	0.0744 (7)
H13	−0.0312	0.0883	0.1572	0.089*
C14	−0.1455 (3)	0.0301 (3)	0.22641 (15)	0.0970 (9)
H14	−0.1707	−0.0500	0.2129	0.116*
C15	−0.1903 (3)	0.0649 (3)	0.27954 (14)	0.0972 (9)
H15	−0.2471	0.0088	0.3020	0.117*
C16	−0.1528 (3)	0.1795 (4)	0.29954 (11)	0.0979 (10)
H16	−0.1808	0.2009	0.3363	0.118*
C17	−0.0707 (3)	0.2690 (3)	0.26554 (10)	0.0747 (7)
H17	−0.0465	0.3492	0.2791	0.090*
O21	0.24129 (17)	0.44753 (12)	0.12929 (6)	0.0603 (4)
C22	0.1556 (2)	0.56025 (17)	0.12009 (8)	0.0513 (5)
C23	0.1895 (3)	0.66578 (19)	0.15090 (9)	0.0625 (5)
H23	0.2681	0.6638	0.1793	0.075*
C24	0.1064 (3)	0.7754 (2)	0.13971 (10)	0.0710 (6)
H24	0.1296	0.8479	0.1604	0.085*
C25	−0.0089 (3)	0.7778 (3)	0.09874 (12)	0.0806 (7)
H25	−0.0669	0.8514	0.0920	0.097*
C26	−0.0401 (3)	0.6730 (3)	0.06736 (12)	0.0868 (8)
H26	−0.1176	0.6759	0.0386	0.104*
C27	0.0425 (3)	0.5617 (2)	0.07787 (10)	0.0716 (6)
H27	0.0211	0.4897	0.0566	0.086*
H51	0.488 (3)	0.0604 (19)	0.1351 (9)	0.063 (6)*
H311	0.578 (3)	0.227 (2)	0.1883 (10)	0.076 (7)*
H312	0.482 (3)	0.277 (3)	0.2376 (12)	0.090 (8)*
H313	0.467 (3)	0.136 (2)	0.2267 (10)	0.078 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0536 (3)	0.0488 (3)	0.0518 (3)	0.0030 (2)	−0.0007 (2)	−0.0055 (2)
O2	0.0721 (9)	0.0631 (9)	0.0608 (9)	0.0006 (7)	−0.0044 (7)	−0.0154 (7)
N3	0.0539 (9)	0.0540 (9)	0.0548 (9)	0.0062 (7)	−0.0092 (7)	−0.0089 (8)
C31	0.0571 (13)	0.0751 (16)	0.0649 (14)	0.0098 (12)	−0.0147 (11)	−0.0099 (13)
N4	0.0536 (9)	0.0488 (9)	0.0549 (9)	0.0051 (7)	−0.0055 (7)	−0.0049 (8)
C5	0.0459 (10)	0.0491 (11)	0.0557 (11)	0.0029 (9)	−0.0030 (9)	0.0013 (9)
O61	0.0632 (8)	0.0660 (9)	0.0641 (9)	0.0094 (7)	−0.0145 (7)	−0.0117 (7)
C62	0.0543 (11)	0.0528 (11)	0.0609 (12)	0.0105 (9)	−0.0054 (9)	−0.0050 (10)
C63	0.0460 (10)	0.0436 (10)	0.0522 (11)	0.0039 (8)	0.0023 (8)	0.0025 (8)
C64	0.0503 (11)	0.0506 (11)	0.0620 (12)	0.0052 (9)	0.0020 (9)	0.0023 (9)
O641	0.0642 (10)	0.0849 (11)	0.1015 (13)	0.0287 (8)	−0.0251 (9)	−0.0147 (10)
C65	0.0747 (14)	0.0566 (13)	0.0934 (17)	0.0078 (11)	0.0187 (13)	−0.0068 (13)
C66	0.110 (2)	0.0545 (14)	0.096 (2)	−0.0043 (14)	0.0463 (17)	−0.0201 (14)
C67	0.114 (2)	0.0811 (18)	0.0693 (16)	−0.0205 (16)	0.0199 (15)	−0.0220 (14)
C68	0.0929 (17)	0.0759 (16)	0.0665 (15)	−0.0072 (14)	−0.0016 (13)	−0.0167 (13)
C69	0.0612 (12)	0.0538 (11)	0.0546 (12)	−0.0031 (9)	0.0050 (9)	−0.0012 (9)
C70	0.0567 (11)	0.0456 (11)	0.0625 (12)	0.0000 (9)	0.0131 (9)	−0.0008 (9)
O11	0.0514 (7)	0.0550 (8)	0.0524 (8)	0.0046 (6)	−0.0027 (6)	0.0034 (6)
C12	0.0425 (10)	0.0618 (12)	0.0587 (12)	0.0117 (9)	−0.0003 (8)	0.0089 (10)
C13	0.0775 (15)	0.0535 (13)	0.0929 (17)	0.0108 (11)	0.0190 (13)	0.0082 (12)
C14	0.092 (2)	0.0692 (17)	0.131 (3)	0.0103 (14)	0.0194 (18)	0.0289 (18)
C15	0.0747 (17)	0.115 (2)	0.101 (2)	0.0013 (17)	−0.0004 (16)	0.046 (2)
C16	0.0648 (15)	0.176 (3)	0.0533 (14)	0.0050 (19)	0.0032 (11)	0.0157 (18)
C17	0.0550 (12)	0.1051 (18)	0.0640 (14)	−0.0002 (12)	0.0025 (10)	−0.0077 (14)
O21	0.0662 (9)	0.0526 (8)	0.0625 (9)	0.0077 (7)	0.0114 (7)	0.0014 (7)
C22	0.0497 (10)	0.0489 (11)	0.0553 (11)	−0.0026 (8)	0.0091 (9)	0.0040 (9)
C23	0.0682 (13)	0.0574 (12)	0.0617 (13)	−0.0049 (10)	−0.0036 (10)	0.0015 (10)
C24	0.0941 (17)	0.0520 (12)	0.0671 (15)	0.0053 (12)	0.0093 (13)	0.0029 (11)
C25	0.0832 (17)	0.0718 (16)	0.0872 (18)	0.0183 (13)	0.0203 (14)	0.0220 (15)
C26	0.0695 (15)	0.106 (2)	0.0840 (18)	0.0013 (15)	−0.0188 (13)	0.0220 (17)
C27	0.0764 (15)	0.0703 (14)	0.0678 (14)	−0.0122 (12)	−0.0118 (12)	−0.0022 (12)

Geometric parameters (Å, º)

P1—O2	1.450 (1)	C68—H68	0.9300
P1—O21	1.579 (1)	C69—C70	1.376 (3)
P1—O11	1.588 (1)	O11—C12	1.408 (2)
P1—N3	1.641 (2)	C12—C17	1.354 (3)
N3—N4	1.384 (2)	C12—C13	1.384 (3)
N3—C31	1.455 (3)	C13—C14	1.365 (3)
C31—H311	0.98 (2)	C13—H13	0.9300
C31—H312	0.92 (3)	C14—C15	1.364 (4)
C31—H313	0.95 (2)	C14—H14	0.9300
N4—C5	1.269 (2)	C15—C16	1.340 (4)
C5—C63	1.460 (3)	C15—H15	0.9300
C5—H51	0.95 (2)	C16—C17	1.424 (4)
O61—C62	1.345 (2)	C16—H16	0.9300
O61—C69	1.375 (2)	C17—H17	0.9300
C62—C63	1.340 (3)	O21—C22	1.408 (2)
C62—H62	0.94 (2)	C22—C27	1.361 (3)
C63—C64	1.459 (2)	C22—C23	1.363 (3)
C64—O641	1.222 (2)	C23—C24	1.377 (3)
C64—C70	1.465 (3)	C23—H23	0.9300
C65—C66	1.372 (4)	C24—C25	1.353 (4)
C65—C70	1.402 (3)	C24—H24	0.9300
C65—H65	0.9300	C25—C26	1.360 (4)
C66—C67	1.374 (4)	C25—H25	0.9300
C66—H66	0.9300	C26—C27	1.387 (4)
C67—C68	1.361 (4)	C26—H26	0.9300
C67—H67	0.9300	C27—H27	0.9300
C68—C69	1.377 (3)
O2—P1—O21	116.86 (8)	C70—C69—C68	122.2 (2)
O2—P1—O11	115.59 (8)	C69—C70—C65	117.6 (2)
O21—P1—O11	99.66 (7)	C69—C70—C64	120.7 (2)
O2—P1—N3	112.98 (9)	C65—C70—C64	121.8 (2)
O21—P1—N3	103.64 (8)	C12—O11—P1	120.54 (11)
O11—P1—N3	106.52 (8)	C17—C12—C13	121.1 (2)
N4—N3—C31	121.4 (2)	C17—C12—O11	121.6 (2)
N4—N3—P1	115.5 (1)	C13—C12—O11	117.15 (19)
C31—N3—P1	123.1 (2)	C14—C13—C12	120.0 (3)
N3—C31—H311	111.2 (15)	C14—C13—H13	120.0
N3—C31—H312	107.1 (17)	C12—C13—H13	120.0
H311—C31—H312	106 (2)	C15—C14—C13	120.0 (3)
N3—C31—H313	110.0 (14)	C15—C14—H14	120.0
H311—C31—H313	114 (2)	C13—C14—H14	120.0
H312—C31—H313	108 (2)	C16—C15—C14	120.3 (3)
C5—N4—N3	118.7 (2)	C16—C15—H15	119.9
N4—C5—C63	120.7 (2)	C14—C15—H15	119.9
N4—C5—H51	123.6 (13)	C15—C16—C17	121.2 (3)
C63—C5—H51	115.7 (13)	C15—C16—H16	119.4
C62—O61—C69	117.9 (2)	C17—C16—H16	119.4
C63—C62—O61	125.9 (2)	C12—C17—C16	117.3 (3)
C63—C62—H62	125.2 (12)	C12—C17—H17	121.4
O61—C62—H62	108.9 (13)	C16—C17—H17	121.4
C62—C63—C64	119.3 (2)	C22—O21—P1	122.30 (12)
C62—C63—C5	122.0 (2)	C27—C22—C23	121.2 (2)
C64—C63—C5	118.7 (2)	C27—C22—O21	117.78 (18)
O641—C64—C63	122.5 (2)	C23—C22—O21	121.00 (18)
O641—C64—C70	122.9 (2)	C22—C23—C24	119.5 (2)
C63—C64—C70	114.5 (2)	C22—C23—H23	120.3
C66—C65—C70	120.1 (2)	C24—C23—H23	120.3
C66—C65—H65	119.9	C25—C24—C23	120.2 (2)
C70—C65—H65	119.9	C25—C24—H24	119.9
C65—C66—C67	120.5 (2)	C23—C24—H24	119.9
C65—C66—H66	119.8	C24—C25—C26	120.1 (2)
C67—C66—H66	119.8	C24—C25—H25	119.9
C68—C67—C66	120.5 (2)	C26—C25—H25	119.9
C68—C67—H67	119.8	C25—C26—C27	120.6 (2)
C66—C67—H67	119.8	C25—C26—H26	119.7
C67—C68—C69	119.1 (3)	C27—C26—H26	119.7
C67—C68—H68	120.5	C22—C27—C26	118.4 (2)
C69—C68—H68	120.5	C22—C27—H27	120.8
O61—C69—C70	121.7 (2)	C26—C27—H27	120.8
O61—C69—C68	116.1 (2)
O2—P1—N3—N4	170.7 (1)	O641—C64—C70—C69	−178.0 (2)
O21—P1—N3—N4	−61.82 (15)	C63—C64—C70—C69	1.1 (3)
O11—P1—N3—N4	42.77 (16)	O641—C64—C70—C65	1.8 (3)
O2—P1—N3—C31	−11.4 (2)	C63—C64—C70—C65	−179.08 (19)
O21—P1—N3—C31	116.05 (19)	O2—P1—O11—C12	−56.98 (16)
O11—P1—N3—C31	−139.35 (19)	O21—P1—O11—C12	176.89 (13)
C31—N3—N4—C5	−1.4 (3)	N3—P1—O11—C12	69.43 (15)
P1—N3—N4—C5	176.5 (1)	P1—O11—C12—C17	70.1 (2)
N3—N4—C5—C63	177.5 (2)	P1—O11—C12—C13	−113.46 (18)
C69—O61—C62—C63	0.2 (3)	C17—C12—C13—C14	2.3 (3)
O61—C62—C63—C64	2.2 (3)	O11—C12—C13—C14	−174.1 (2)
O61—C62—C63—C5	−177.17 (18)	C12—C13—C14—C15	−1.4 (4)
N4—C5—C63—C62	0.0 (3)	C13—C14—C15—C16	−0.8 (4)
N4—C5—C63—C64	−179.4 (2)	C14—C15—C16—C17	2.2 (4)
C62—C63—C64—O641	176.4 (2)	C13—C12—C17—C16	−0.9 (3)
C5—C63—C64—O641	−4.2 (3)	O11—C12—C17—C16	175.35 (19)
C62—C63—C64—C70	−2.7 (3)	C15—C16—C17—C12	−1.3 (4)
C5—C63—C64—C70	176.66 (16)	O2—P1—O21—C22	−57.06 (17)
C70—C65—C66—C67	−1.4 (4)	O11—P1—O21—C22	68.20 (15)
C65—C66—C67—C68	1.1 (4)	N3—P1—O21—C22	177.96 (14)
C66—C67—C68—C69	0.5 (4)	P1—O21—C22—C27	−111.79 (19)
C62—O61—C69—C70	−2.0 (3)	P1—O21—C22—C23	70.8 (2)
C62—O61—C69—C68	178.1 (2)	C27—C22—C23—C24	0.9 (3)
C67—C68—C69—O61	178.2 (2)	O21—C22—C23—C24	178.18 (18)
C67—C68—C69—C70	−1.7 (4)	C22—C23—C24—C25	0.5 (4)
O61—C69—C70—C65	−178.57 (18)	C23—C24—C25—C26	−1.8 (4)
C68—C69—C70—C65	1.3 (3)	C24—C25—C26—C27	1.7 (4)
O61—C69—C70—C64	1.2 (3)	C23—C22—C27—C26	−1.1 (3)
C68—C69—C70—C64	−178.8 (2)	O21—C22—C27—C26	−178.4 (2)
C66—C65—C70—C69	0.2 (3)	C25—C26—C27—C22	−0.2 (4)
C66—C65—C70—C64	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C31—H312···O2	0.92 (3)	2.50 (3)	3.013 (3)	116 (2)
C5—H51···O641	0.95 (2)	2.49 (2)	2.828 (2)	101 (2)
C65—H65···O641	0.94	2.62	2.873 (3)	96
C62—H62···N4	0.94 (2)	2.62 (2)	2.819 (3)	92 (1)