Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

A three-dimensional hydrogen-bonded network based on a rare mok topology has been constructed using an organic molecule synthesized in the solid state. The molecule is obtained using a supramolecular protecting-group strategy that is applied to a solid-state [2+2] photodimerization. The photodimerization affords a novel head-to-head cyclo­butane product. The cyclo­butane possesses tetrahedrally disposed cis-hydrogen-bond donor (phenolic) and cis-hydrogen-bond acceptor (pyridyl) groups. The product self-assembles in the solid state to form a mok network that exhibits twofold interpenetration. The cyclo­butane adopts different conformations to provide combinations of hydrogen-bond donor and acceptor sites to conform to the structural requirements of the mok net.

1. Introduction

Efforts of chemists to develop new avenues to form covalent bonds and generate molecules that diversify chemical space are increasingly important (e.g. materials science, medicine; Dobson, 2004). In this context, chemical reactions performed in organic crystals can be used to synthesize molecules that possess functional groups with stereochemical relationships which are not accessible in solution (Elacqua et al., 2012; Oburn et al., 2017). The stereochemical outcome of a reaction in the crystalline state is generally dictated by topological arrangement or supramolecular organization in a lattice (Biradha & Santra, 2013; Ramamurthy & Sivaguru, 2016; Vittal & Quah, 2017). A well established reaction to proceed in the solid state is the [2+2] photodimerization of alkenes that generates carbon–carbon single (C—C) bonds in the form of cyclo­butane rings. The reaction is a mainstay for crystal engineers that seek to form covalent bonds in solids. In recent years, cyclo­addition, when controlled by hydrogen bonds (e.g. resorcinol or res templates) and principles of self-assembly, has enabled the synthesis of complex organic molecules based on unique topologies (e.g. ladderanes; Sinnwell et al., 2015; Lange et al., 2017; Gao et al., 2004).

A current goal of crystal engineers, and general efforts of solid-state chemists, is to design molecular building blocks that self-assemble to form extended (i.e. one-, two- and three-dimensional) network topologies. Of particular interest are entangled nets, wherein nodes are linked to form intertwined and self-catenated structures. The mok net, which is comprised of tetrahedral nodes linked in three-dimensions – akin to the well known diamondoid net – is one such example (Fig. 1) (O'Keeffe, 1991; Alexandrov et al., 2012; Bonneau & O'Keeffe, 2015). Self-catenation of the mok net is based on the shortest rings (six-membered rings, blue), with interpenetration of two hexagonal (hcb) subnets of the mok net effectively facilitating the self-catenation. A consequence of the self-catenation is the generation of two additional rings (six- and eight-membered, orange and purple, respectively). Importantly, the mok net has only been observed in assembly processes based on metal–organic components wherein the tetrahedral node is supplied by a metal center (Gong et al., 2011; Zhang et al., 2015; Liang et al., 2013). Moreover, the mok net has been recognized by O'Keeffe as `likely to be difficult to achieve chemically' in the solid state due to its intricacy. An organic molecule that fulfills the role of the tetrahedral nodes in a mok net has not yet been identified.

Figure 1 Post-installation of phenolic groups.

With this in mind, we report here the supramolecular solid-state construction of the organic molecule rctt-1,2-bis­(4-pyridyl)-3,4-bis­(4-phenol)cyclo­butane (1a), showing it self-assembles in the solid state to form a network that conforms to the mok topology. The synthesis is achieved using a novel supramolecular protecting-group strategy applied to phenols and utilizes 4,6-di­iodo-res (diI-res) as a hydrogen-bond donor template (Elacqua et al., 2012). This strategy enables protection of terminal phenolic groups from participating in hydrogen bonds in the solid state and then post-installation of cis-phenolic groups onto a cyclo­butane ring system (Fig. 1). We show that the head-to-head (HH) cyclo­butane 1a, following removal from the molecular template, self-assembles as a pure form to produce a hydrogen-bonded twofold interpenetrated net of mok topology. Within the network, the cyclo­butane ring of 1a acts as a node with the radial phenolic and pyridyl groups serving as hydrogen-bond donor and acceptor linkers, respectively, resulting in the first purely organic mok network (Gong et al., 2011; Liang et al., 2013; Zhang et al., 2015; Li et al., 2017).

2. Results and discussion

The HH cyclo­butane 1a contains cis-4-phenolic and cis-4-pyridyl groups. Although cyclo­butanes functionalized with cis-4-pyridyl groups have been synthesized in the solid state using hydrogen bonds with res templates, the template-directed synthesis of a cyclo­butane lined with phenolic groups has not yet been reported. We note that the synthesis of 1a itself has not been reported in either solution or the solid state, although a photodimerization of protonated 1b (1b = trans-1-(4-phenol)-2-(4-pyridyl)­ethyl­ene) in HCl has been shown to yield a mixture of head-to-tail (HT) isomers (Zhang et al., 2000). To us, 1a was attractive as a building block in supramolecular chemistry given the presence of the radial and tetrahedrally disposed hydrogen-bond donor (phenol) and acceptor (pyridyl) groups. We expected the groups to equip 1a with a capacity to form 4-connected nets (e.g. diamondoid) (Ermer, 1988; Baburin et al., 2008). Many conformations furnished by the hydrogen-bond donor groups would equip 1a with a capacity to form different 4-connected nets. While 1b has been a subject of numerous studies (e.g. liquid crystals), we were also surprised that the crystal structure of 1b had not been reported.

The ability of the symmetrical cyclo­butane rctt-tetra­kis­(4-pyridyl)­cyclo­butane (tpcb) (D_2h symmetry) to serve as a tetrahedral node of extended nets composed of metal and organic building blocks was originally elucidated by Schroder and Champness (Blake et al., 1997). Specifically, tpcb served as a 4-connected node to support a net of composition [Ag(tpcb)]BF₄ (Blake et al., 1997; Liu et al., 2011). We expected the cyclo­butane 1a, being of lower symmetry (C_s), to be able to interact with itself, in contrast to tpcb, by way of complementary hydrogen-bond donor and acceptor groups. The presence of the donor and acceptor sites attached to the cyclo­butane ring would equip the molecule with a capacity to self-assemble into a net purely organic in composition.

2.1. Photostable parent alkene 1b

Plate-like single crystals of 1b were grown by slow evaporation in MeOH/ethyl acetate (1:1, v:v) over a period of 10 d, crystallizing in the orthorhombic space group Pca2₁. The molecule adopts a planar conformation (twist: 1.63°) with the hydroxyl and pyridyl groups participating in intermolecular O—H⋯N hydrogen bonds [O⋯N, O—H⋯N: 2.729 (5) Å, 177.8 (2)°] (Fig. 2). The alkene self-assembles to form chains along the a axis that stack HH and edge-to-face. Nearest-neighbor C=C bonds are separated by 5.65 Å, which is beyond the limit of the work by Schmidt (1971). When subjected to UV-radiation (450 W medium-pressure Hg lamp) for a period of up to 50 h, 1b was determined to be photostable.

Figure 2 X-ray structure of photostable 1b: (a) hydrogen-bonded chains and (b) stacked C=C bonds of nearest-neighbour alkenes.

2.2. Attempts to form cocrystals of 1b

While 1b is photostable, attempts to cocrystallize 1b with diI-res and, in doing so, form a cocrystal with 1b stacked HH, to react to form the cyclo­butane 1a were unsuccessful (Fig. 1). Liquid-assisted grinding of 1b with diI-res afforded a mixture of the two solids, as demonstrated by powder X-ray diffraction. Attempts to grow cocrystals from solution were also unsuccessful. The solution crystallization experiments typically produced a powder that was identified as the alkene 1b. We attributed the inability of diI-res to form a cocrystal with 1b to the inability of diI-res to compete with the hydrogen bonding between the phenolic and pyridyl groups present in crystalline 1b [Fig. 2(a)] (Elacqua et al., 2012).

2.3. Supramolecular protecting-group strategy

While 1b is photostable as a pure solid, we determined that the C=C bonds of 1b are made photoactive when the protected methyl ester 1c (1c = trans-1-(4-acet­oxy)-2-(4-pyridyl)­ethyl­ene) is cocrystallized with diI-res in a newly designed supramolecular protecting-group strategy (Elacqua et al., 2012). For the strategy, we aimed to develop a method that would allow us to mask the hydrogen bonding ability of the OH group and, at the same time, have minimum steric impact on the requirement of the C=C bonds to stack parallel and on the order of 4.2 Å. Given that cinnamates are known to stack and photodimerize in the solid state (Lewis et al., 1984), we targeted the ester linkage. Specifically, we expected acyl­ation of the phenol moiety of 1b to allow the C=C bonds of 1b in the form of 1c to stack in the solid state and conform to the topochemical postulate for a photoreaction. Acyl­ation of 1b was thus performed and afforded 1c in high yield (Yin et al., 2011).

2.4. Photostable protected alkene 1c

Plate-like single crystals of 1c were generated by slow evaporation in ethyl acetate/ethanol (3:2, v:v) over a period of 2 d. As in the case of 1b, the alkene 1c is photostable [Fig. 3(a)] and crystallizes in the orthorhombic space group Pbca. The aromatic rings lie approximately coplanar (twist: 4.66°) with the acet­oxy group twisted from coplanarity (twist: 63.9°). The alkene packs HH and edge-to-face with the nearest C=C bonds separated by 4.74 Å, which is also beyond the limit of the work by Schmidt (1971) [Fig. 3(b)]. UV-radiation for up to 50 h revealed 1c to be photostable.

Figure 3 X-ray structures of 1c and (diI-res)·2(1c): (a) edge-to-face forces of 1c, (b) C=C bond interactions of nearest-neighbour alkenes of 1c, (c) hydrogen-bonded three-component assembly (diI-res)·2(1c) (top) with C=C separations (bottom) and (d) two-dimensional sheets of (diI-res)·2(1c).

2.5. Photoreactive cocrystal 1c

Although 1c as a pure form is photostable, cocrystals of the alkene using the supramolecular protecting-group strategy with diI-res are photoactive and generate the cyclo­butane 1d [where: 1d = 1,2-bis­(4-pyridyl)-3,4-bis­(4-acet­oxy­phenyl) cyclo­butane] regioselectively and in quantitative yield.

Single crystals of (diI-res)·2(1c) in the form of colorless plates were formed by combining solutions of 1c (50 mg, 0.21 mmol) in ethyl acetate (3 ml) and diI-res (56 mg, 0.16 mmol) in EtOH (2 ml). The components of (diI-res)·2(1c) crystallize in the triclinic space group . The molecules form three-component assemblies sustained by two O—H⋯N hydrogen bonds [O⋯N, O—H⋯N: 2.677 (5) Å, 167.1 (4)°; 2.725 (5) Å, 172.6 (3)°] [Fig. 3(c)]. The rings of the alkene, in contrast to 1b and pure 1c, stack HH and face-to-face with the acet­oxy groups twisted from planarity (twists: 41.8, 74.1°). The stacked C=C bonds lie parallel and are separated by 3.93 Å, which conforms to the geometry determined by Schmidt (1971). The assemblies interact via a halogen bond (Metrangolo & Resnati, 2014) [I⋯O: 3.309 (3), 3.227 (4) Å, θ = 159.1 (1), 174.8 (1)°] to give two-dimensional sheets in the crystallographic ac plane with neighboring C=C bonds separated by 5.93 Å.

To determine the reactivity of (diI-res)·2(1c), a finely ground crystalline powder was spread between two glass plates and exposed to broadband UV irradiation. A ¹H NMR spectrum revealed the complete disappearance of alkene signals (7.19 and 7.56 p.p.m.) and the appearance of a cyclo­butane signal (4.58 p.p.m.) following 100 h of UV-irradiation (see supporting information).

To determine the stereochemistry of the photoproduct, single crystals as colorless prisms were obtained by recrystallization of the reacted solid from ethanol/ethyl acetate (1:1, v:v) over a period of 3 d. The components of (diI-res)·(1d) crystallize in the monoclinic space group P2₁/c with the stereochemistry being confirmed as the rctt isomer 1d (Fig. 4). The solid is composed of two-component assemblies sustained by two O—H⋯N hydrogen-bonds [O⋯N, O—H⋯N: 2.658 (6) Å, 153.4 (3)°; 2.704 (6) Å, 170.9 (3)°], with I⋯O halogen bonds also formed involving the carboxyl O atom of 1d [I⋯O: 3.442 (9) Å, θ = 144.9 (2)°]. Additionally, I⋯O halogen bonds are present involving a hydroxyl O atom [I⋯O: 3.436 (4) Å, θ = 152.6 (2)°] to generate ribbons along the crystallographic c axis.

Figure 4 X-ray structure of (diI-res)·(1d): (a) hydrogen bonds and (b) I⋯O halogen bonds.

2.6. Rare organic mok net

The synthesis of the targeted unsymmetrical cyclo­butane 1a was next achieved in the deprotection of 1d by treating the photoreacted solid of (diI-res)·(1d) with NaOH as base (see supporting information). Single crystals of 1a suitable for single-crystal X-ray diffraction were obtained by slow solvent evaporation from solution of aqueous MeOH over a period of 5 d.

The asymmetric unit of 1a consists of two unique cyclo­butanes (CB1 and CB2) that crystallize in the monoclinic space group I2/a. The deprotection of 1d with the removal of the acet­oxy protecting group confirmed the rctt stereochemistry of the cyclo­butane ring of 1a (Fig. 5). A remarkable feature of the crystal structure of 1a is that the cyclo­butane self-assembles to generate a three-dimensioanl hydrogen-bonded framework of mok topology (point symbol 6^5.8). The nodes of the mok are defined by the centroids of the cyclo­butane rings of 1a (Fig. 6) (Blatov et al., 2014). The cyclo­butanes provide tetrahedrally disposed and cisoid hydrogen-bond donor and acceptor sites to form the 4-connected net.

Figure 5 X-ray structure of 1a: (a) anti–gauche 1a (CB1) and (b) syn–anti 1a (CB2). Note: anti and syn are designated relative to the pyridyl groups.

Figure 6 X-ray structure of mok topology of 1a: (a) interpenetration of hexagonal (hcb) sub-nets highlighted in green and blue, (b) building blocks of cyclo­butanes as nodes to form hydrogen-bonded hexagons numbered in a clockwise manner (hydrogens removed for clarity), (c) connections of two hcb nets (connection highlighted in orange and hcb nets in blue/green), and (d) twofold interpenetrated mok nets highlighted separately in tan and blue.

The pattern of hydrogen bonding that defines the mok net of 1a is complex. The complexity arises since the hydroxyl groups of 1a adopt two different conformations – CB1 and CB2 – within the net. Each conformation is based on the relative dispositions of the hydroxyl groups of each molecule (Fig. 5). More specifically, CB1 adopts an anti–gauche conformation wherein the hydroxyl groups are anti and gauche relative to the cis-4-pyridyl groups [Fig. 5(a)]. The phenyl group related to the gauche orientation of CB1 is disordered [occupancies: site A 0.90 (1); site B 0.10 (1); see supporting information]. CB2 adopts an anti–syn conformation whereby the hydroxyl groups are anti and syn relative to the cis-4-pyridyls [Fig. 5(b)]. The cyclo­butane self-assembles to form the mok network with all OH and N-pyridyl groups participating in O—H⋯N hydrogen bonds (Table 1).

Table 1
Selected hydrogen-bond distances and angles

Molecule	Distance (Å)	O—H⋯N angle (°)
CB1
O1(anti)⋯N4	2.764 (3)	163.96 (3)
O2(gauche)⋯N3	2.676 (3)	167.71 (3)
CB2
O3(syn)⋯N1	2.812 (3)	174.94 (3)
O4(anti)⋯N2	2.733 (3)	166.49 (3)

The self-catenation of the mok net arises from interconnection of two twofold interpenetrated hcb layers [blue and green, Fig. 6(a)]. The self-assembly of the cyclo­butanes is manifested with CB1 and CB2 alternating as adjacent nodes throughout the net [Fig. 6(b)]. All rings of the mok network are thus composed of CB1 and CB2 which alternate via the O—H⋯N hydrogen bonds.

The compositions of the hydrogen bonds between adjacent cyclo­butanes are defined by the orientations (i.e. syn, anti, gauche) of the OH groups of the phenols. Specifically, a primary six-membered ring of the hcb subnet involves nodes with hydrogen bonds of alternating two anti orientations [11.53 Å (CB1), 11.49 Å (CB2)] and one syn orientation (12.15 Å). The phenol groups in the gauche (11.81 Å) orientation interconnect the twofold interpenetrated hcb subnets [orange, Fig. 6(c)] and complete the self-catenation. A secondary six-membered ring is generated from interconnection of the hcb subnets (Fig. 7). The secondary six-membered ring involves nodes with hydrogen bonds of alternating two anti orientations (CB1, CB2) and one gauche orientation. Additionally, eight-membered rings are generated from the interconnection of three hcb subnets, involving nodes of alternating one anti (CB1 or CB2), one gauche and one syn orientation.

Figure 7 Hydrogen bonding and rings of mok net 1a: (a) three linkages with CB1 and CB2 (light blue = syn linkage; dark blue = anti linkage; orange = gauche linkage) of a primary six-membered ring, (b) space-filling of primary six-membered ring, (c) primary six-membered ring showing linkages within hcb subnet, (d) two types of linkages of a secondary six-membered ring, (e) space-filling view of secondary six-membered ring, (f) highlighted secondary six-membered ring within mok net, (g) three types of linkages within an eight-membered ring, (h) stick-view of eight-membered ring with anti-orientation from CB1, and (i) space-filling of eight-membered ring showing two interdigitated hcb subnets (hydrogen atoms omitted for clarity).

The mok framework of 1a also exhibits the overall twofold interpenetration [Fig. 6(d)]. Highly disordered electron density consistent with MeOH as solvent is located in lacunae (∼180 ų) (Spek, 2015) at the intersection of the interpenetrated hcb and mok subnets and nets, respectively. The mok net of 1a was, before now, an unrealized network in structures of purely organic solids.

2.7. A mok net purely organic in origin

The mok net 1a represents a rare family of entanglements that have only been realized in coordination polymers and metal–organic frameworks. For metal–organic materials, the metal centers and organic linkers are nodes and bridges, respectively, Gong et al., 2011; Liang et al., 2013; Zhang et al., 2015). O'Keeffe has pointed out that a single mok net can be considered difficult to achieve chemically given that one distance between two nodes is shorter than the distance between linked nodes. The short distance of a mok net corresponds to two nodes between the interpenetrated hcb layers. For 1a the corresponding distances are 10.1 Å (non-linked nodes) and 11.5 Å (linked nodes); however, we note that here the twofold interpenetration generates much shorter distances between nodes of two separate nets of the interpenetrated structure (i.e. 6.07, 6.38 Å).

A major factor that defines how 1a supports the formation of the mok net relates to the different orientations that the cyclo­butane assumes to define the nodes and edges of the network. Two copies of the same molecule that are present in two different conformations (i.e. CB1 and CB2) self-assemble to form the network. The conformations support the four different types of linkages (i.e. anti (2), syn, gauche) to create six- and eight-membered rings. In doing so, the cyclo­butanes for both the six- and eight-membered rings act as either double hydrogen-bond donors (DD), double hydrogen-bond acceptors (AA) or a donor/acceptor (DA) (Table 2, Fig. 7). The AA linkages involve acceptor pyridyls in the 3,4-position of the cyclo­butane ring, whereas the acceptors of the DA linkages are fixed in either the 3-position (3-acceptor) or 4-position (4-acceptor) of the ring. The cyclo­butane 1a effectively adapts to conform to the topology of the mok net by using chemical information stored at the molecular level (i.e. cyclo­butane and conformation) that is then expressed as required at the supramolecular (i.e. hydrogen-bond donor and acceptor capacities) level.

Table 2
Unique rings of 1a mok network

No.	Cyclo­butane	Overall type†	Donor type	Acceptor type
Six-membered rings
Primary
1	CB2	DD	syn, anti	–
2	CB1	DA	anti	3-acceptor
3	CB2	DA	syn	3-acceptor
4	CB1	DA	anti	4-acceptor
5	CB2	DA	anti	4-acceptor
6	CB1	AA	–	3,4-acceptor
Secondary
7	CB1	DD	anti/gauche	–
8	CB2	DA	anti	4-acceptor
9	CB1	DA	gauche	4-acceptor
10	CB2	DA	anti	3-acceptor
11	CB1	DA	anti	3-acceptor
12	CB2	AA	–	3,4-acceptor
Eight-membered rings
1,5	CB1	DD	anti, gauche	–
2,6	CB2	DA	syn	4-acceptor
3,7	CB1	DA	gauche	3-acceptor
4,8	CB2	AA	–	3,4-acceptor

†Cyclo­butane participation in six- and eight-membered rings as AA = double hydrogen-bond acceptors, DD = double hydrogen-bond donors, or DA = hydrogen-bond donor and acceptor.

3. Conclusions

We have reported the first mok network composed of purely organic components. The cyclo­butane 1a contains a combination of tetrahedrally disposed (Zhang et al., 2012) hydrogen-bond donor and acceptor sites synthesized in the solid state using a newly developed supramolecular protecting-group strategy. Hydroxyl donor sites, which add a second degree of flexibility, are used to achieve the unique topology. We believe our observation of the building block 1a to support different network linkages to form the mok net serves as an important example on how to achieve supramolecular complexity from redundant molecular information. The fact that the solid state can be exploited for such design, particularly given the high degree of control of directionality for covalent bond formation, can be expected to encourage further work in the field.

4. Related literature

The following references are cited in the supporting information: Sheldrick (2015a,b); Spek (2003); Blatov et al. (2016, 2010); Alexandrov et al. (2011); Kraus & Nolze (1996).

Supporting information

Computing details

Data collection: Collect (Hooft, 1998) for mcg16180lt, mcg16122, web134, mcg16113; APEXII V2014.1 (Bruker AXS, Inc., 2014) for web006. Cell refinement: HKL SCALEPACK (Otwinowski and Minor, 1997) for mcg16180lt, mcg16122, web134, mcg16113; APEXII V2014.1 (Bruker AXS, Inc., 2014) for web006. Data reduction: DENZO (Otwinowski and Minor, 1997) for mcg16180lt, web134; SAINT V8.34A (Bruker AXS Inc., 2013) for mcg16122, web006, mcg16113. For all structures, program(s) used to solve structure: ShelXT (Sheldrick, 2015). Program(s) used to refine structure: SHELXL (Sheldrick, 2008) for mcg16180lt, web134; SHELXL (Sheldrick, 2015) for mcg16122, mcg16113; SHELXL2014/7 (Sheldrick, 2014) for web006. For all structures, molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(mcg16180lt)

Crystal data

C13H11NO	Dx = 1.284 Mg m^−3
Mr = 197.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2440 reflections
a = 23.354 (3) Å	θ = 22.4–3.5°
b = 5.6449 (7) Å	µ = 0.08 mm^−1
c = 7.7373 (10) Å	T = 190 K
V = 1020.0 (2) Å^3	Colorless, plate
Z = 4	0.17 × 0.09 × 0.02 mm
F(000) = 416

Data collection

Nonius Kappa CCD diffractometer	1384 independent reflections
Radiation source: fine-focus sealed tube	866 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.062
CCD rotation images, phi and ω scans	θmax = 23.2°, θmin = 3.2°
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0661 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.9249. The λ/2 correction factor is 0.00150.	h = −25→25
Tmin = 0.991, Tmax = 0.999	k = −6→6
11876 measured reflections	l = −7→8

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0177P)^2 + 0.2791P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max < 0.001
wR(F^2) = 0.076	Δρmax = 0.24 e Å^−3
S = 1.02	Δρmin = −0.11 e Å^−3
1384 reflections	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
138 parameters	Extinction coefficient: 0.0010 (6)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.5

Special details

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.

Refinement. Refined as a 2-component perfect inversion twin.

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

	x	y	z	Uiso*/Ueq
O1	0.65531 (14)	−0.0963 (5)	0.4799 (5)	0.0659 (10)
H1	0.6833	−0.0044	0.4928	0.099*
N1	0.24807 (17)	0.8078 (6)	0.5210 (5)	0.0635 (13)
C13	0.6056 (2)	0.0295 (8)	0.4899 (6)	0.0479 (12)
C8	0.5026 (2)	0.2782 (8)	0.5081 (6)	0.0509 (12)
C12	0.6029 (2)	0.2432 (8)	0.5769 (6)	0.0574 (14)
H12	0.6360	0.3053	0.6320	0.069*
C9	0.5062 (2)	0.0624 (9)	0.4221 (6)	0.0548 (14)
H9	0.4730	−0.0008	0.3684	0.066*
C11	0.5519 (2)	0.3654 (8)	0.5834 (6)	0.0573 (14)
H11	0.5506	0.5138	0.6412	0.069*
C7	0.4496 (2)	0.4210 (8)	0.5265 (6)	0.0595 (15)
H7	0.4530	0.5650	0.5892	0.071*
C4	0.3486 (2)	0.7410 (10)	0.5745 (6)	0.0569 (14)
H4	0.3833	0.7972	0.6237	0.068*
C5	0.3474 (2)	0.5250 (9)	0.4899 (6)	0.0578 (14)
C3	0.2990 (2)	0.8752 (8)	0.5873 (7)	0.0602 (14)
H3	0.3010	1.0228	0.6460	0.072*
C6	0.3993 (2)	0.3717 (8)	0.4669 (6)	0.0600 (15)
H6	0.3948	0.2281	0.4042	0.072*
C1	0.2481 (2)	0.5981 (9)	0.4422 (7)	0.0708 (17)
H1A	0.2128	0.5427	0.3962	0.085*
C2	0.2957 (2)	0.4551 (9)	0.4227 (6)	0.0661 (16)
H2	0.2926	0.3087	0.3629	0.079*
C10	0.5571 (2)	−0.0621 (8)	0.4132 (6)	0.0566 (14)
H10	0.5587	−0.2099	0.3546	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.072 (2)	0.0469 (19)	0.079 (3)	−0.0034 (17)	−0.001 (2)	−0.009 (2)
N1	0.072 (3)	0.045 (2)	0.074 (3)	−0.011 (2)	−0.022 (3)	0.021 (3)
C13	0.066 (4)	0.040 (3)	0.038 (3)	−0.002 (3)	−0.001 (3)	−0.003 (3)
C8	0.068 (3)	0.046 (3)	0.038 (3)	0.001 (3)	−0.003 (3)	0.011 (3)
C12	0.069 (4)	0.050 (3)	0.053 (3)	0.001 (3)	−0.021 (3)	−0.010 (3)
C9	0.067 (4)	0.058 (4)	0.039 (3)	−0.023 (3)	0.000 (3)	−0.001 (3)
C11	0.083 (4)	0.038 (3)	0.050 (3)	−0.003 (3)	−0.022 (3)	−0.006 (3)
C7	0.083 (3)	0.052 (3)	0.044 (4)	−0.026 (3)	−0.016 (3)	0.019 (3)
C4	0.049 (3)	0.073 (4)	0.049 (3)	−0.019 (3)	−0.009 (3)	0.020 (3)
C5	0.074 (4)	0.052 (4)	0.047 (3)	−0.011 (3)	−0.006 (3)	0.019 (3)
C3	0.078 (3)	0.052 (3)	0.051 (3)	−0.025 (3)	−0.012 (3)	0.015 (3)
C6	0.082 (4)	0.055 (3)	0.044 (4)	−0.028 (3)	−0.003 (3)	0.007 (3)
C1	0.070 (4)	0.057 (3)	0.085 (4)	−0.010 (3)	−0.038 (3)	0.026 (4)
C2	0.086 (4)	0.048 (3)	0.064 (4)	−0.012 (3)	−0.026 (4)	0.019 (3)
C10	0.079 (4)	0.044 (3)	0.047 (3)	−0.016 (3)	0.008 (3)	−0.010 (3)

Geometric parameters (Å, º)

O1—C13	1.364 (5)	C7—C6	1.293 (6)
O1—H1	0.8400	C7—H7	0.9500
N1—C1	1.331 (5)	C4—C5	1.384 (6)
N1—C3	1.351 (5)	C4—C3	1.387 (6)
C13—C10	1.379 (6)	C4—H4	0.9500
C13—C12	1.383 (5)	C5—C2	1.372 (6)
C8—C11	1.381 (6)	C5—C6	1.500 (6)
C8—C9	1.390 (6)	C3—H3	0.9500
C8—C7	1.484 (6)	C6—H6	0.9500
C12—C11	1.377 (6)	C1—C2	1.382 (6)
C12—H12	0.9500	C1—H1A	0.9500
C9—C10	1.383 (6)	C2—H2	0.9500
C9—H9	0.9500	C10—H10	0.9500
C11—H11	0.9500
C13—O1—H1	109.5	C5—C4—H4	120.1
C1—N1—C3	115.1 (4)	C3—C4—H4	120.1
O1—C13—C10	118.6 (4)	C2—C5—C4	116.8 (5)
O1—C13—C12	121.4 (4)	C2—C5—C6	120.0 (5)
C10—C13—C12	119.9 (4)	C4—C5—C6	123.2 (5)
C11—C8—C9	117.6 (5)	N1—C3—C4	123.7 (5)
C11—C8—C7	117.5 (5)	N1—C3—H3	118.2
C9—C8—C7	124.9 (5)	C4—C3—H3	118.2
C11—C12—C13	119.6 (4)	C7—C6—C5	124.6 (5)
C11—C12—H12	120.2	C7—C6—H6	117.7
C13—C12—H12	120.2	C5—C6—H6	117.7
C10—C9—C8	121.5 (5)	N1—C1—C2	124.7 (5)
C10—C9—H9	119.3	N1—C1—H1A	117.7
C8—C9—H9	119.3	C2—C1—H1A	117.7
C12—C11—C8	121.8 (5)	C5—C2—C1	119.9 (5)
C12—C11—H11	119.1	C5—C2—H2	120.1
C8—C11—H11	119.1	C1—C2—H2	120.1
C6—C7—C8	127.4 (5)	C13—C10—C9	119.6 (5)
C6—C7—H7	116.3	C13—C10—H10	120.2
C8—C7—H7	116.3	C9—C10—H10	120.2
C5—C4—C3	119.8 (5)
O1—C13—C12—C11	179.7 (4)	C5—C4—C3—N1	0.0 (7)
C10—C13—C12—C11	−1.3 (7)	C8—C7—C6—C5	−179.8 (4)
C11—C8—C9—C10	0.5 (7)	C2—C5—C6—C7	−179.4 (5)
C7—C8—C9—C10	−178.8 (5)	C4—C5—C6—C7	1.8 (7)
C13—C12—C11—C8	1.4 (7)	C3—N1—C1—C2	−1.4 (7)
C9—C8—C11—C12	−1.0 (7)	C4—C5—C2—C1	−0.3 (7)
C7—C8—C11—C12	178.4 (4)	C6—C5—C2—C1	−179.2 (5)
C11—C8—C7—C6	−179.8 (5)	N1—C1—C2—C5	1.2 (8)
C9—C8—C7—C6	−0.4 (8)	O1—C13—C10—C9	179.9 (4)
C3—C4—C5—C2	−0.3 (7)	C12—C13—C10—C9	0.8 (7)
C3—C4—C5—C6	178.6 (4)	C8—C9—C10—C13	−0.5 (7)
C1—N1—C3—C4	0.8 (7)

(mcg16122)

Crystal data

C15H13NO2	Dx = 1.307 Mg m^−3
Mr = 239.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5803 reflections
a = 10.5366 (11) Å	θ = 2.3–22.7°
b = 7.4255 (7) Å	µ = 0.09 mm^−1
c = 31.091 (3) Å	T = 190 K
V = 2432.5 (4) Å^3	Plate, colorless
Z = 8	0.27 × 0.26 × 0.02 mm
F(000) = 1008

Data collection

Nonius Kappa CCD diffractometer	1517 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.072
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0790 before and 0.0685 after correction. The Ratio of minimum to maximum transmission is 0.9038. The λ/2 correction factor is 0.00150.	θmax = 25.3°, θmin = 2.3°
Tmin = 0.977, Tmax = 0.999	h = −12→12
30658 measured reflections	k = −8→8
2205 independent reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	All H-atom parameters refined
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.0899P)^2 + 1.5926P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
2205 reflections	Δρmax = 0.21 e Å^−3
215 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.55896 (19)	0.5816 (3)	0.61256 (6)	0.0375 (6)
O1	0.71992 (19)	0.7630 (3)	0.59268 (6)	0.0422 (6)
N1	0.6330 (3)	0.4960 (4)	0.95677 (8)	0.0459 (7)
C8	0.6347 (2)	0.5899 (3)	0.74464 (9)	0.0265 (6)
C7	0.6587 (3)	0.5732 (4)	0.79076 (9)	0.0289 (7)
C11	0.5237 (3)	0.6678 (4)	0.72741 (10)	0.0296 (7)
C5	0.6071 (3)	0.5865 (4)	0.86888 (9)	0.0302 (7)
C12	0.5024 (3)	0.6703 (4)	0.68374 (10)	0.0312 (7)
C9	0.7223 (3)	0.5178 (4)	0.71563 (9)	0.0308 (7)
C6	0.5869 (3)	0.6275 (4)	0.82330 (10)	0.0325 (7)
C13	0.5901 (3)	0.5941 (4)	0.65610 (9)	0.0295 (7)
C10	0.7018 (3)	0.5193 (4)	0.67174 (10)	0.0324 (7)
C14	0.6350 (3)	0.6640 (4)	0.58275 (9)	0.0356 (7)
C4	0.5135 (3)	0.6248 (4)	0.89887 (10)	0.0364 (8)
C2	0.7160 (3)	0.5030 (4)	0.88478 (10)	0.0361 (7)
C3	0.5289 (3)	0.5773 (4)	0.94109 (11)	0.0428 (8)
C1	0.7242 (3)	0.4615 (5)	0.92774 (10)	0.0427 (8)
C15	0.5977 (4)	0.6138 (7)	0.53839 (12)	0.0548 (10)
H7	0.736 (3)	0.504 (4)	0.7978 (9)	0.036 (8)*
H1	0.804 (3)	0.403 (4)	0.9377 (10)	0.052 (10)*
H3	0.464 (3)	0.599 (4)	0.9626 (11)	0.055 (10)*
H6	0.514 (3)	0.690 (5)	0.8171 (10)	0.053 (10)*
H4	0.437 (3)	0.679 (4)	0.8895 (10)	0.045 (9)*
H2	0.783 (3)	0.466 (4)	0.8665 (10)	0.045 (9)*
H12	0.422 (3)	0.717 (5)	0.6708 (10)	0.056 (10)*
H9	0.804 (3)	0.468 (4)	0.7279 (9)	0.032 (8)*
H11	0.464 (3)	0.709 (4)	0.7476 (11)	0.051 (10)*
H10	0.757 (4)	0.468 (4)	0.6517 (10)	0.053 (10)*
H15A	0.614 (6)	0.495 (9)	0.530 (2)	0.16 (3)*
H15B	0.639 (5)	0.691 (7)	0.5180 (16)	0.113 (19)*
H15C	0.507 (6)	0.607 (7)	0.5367 (17)	0.12 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0348 (11)	0.0453 (13)	0.0323 (12)	−0.0043 (9)	−0.0047 (9)	−0.0043 (9)
O1	0.0378 (12)	0.0480 (13)	0.0409 (13)	−0.0060 (11)	−0.0039 (9)	−0.0009 (10)
N1	0.0491 (17)	0.0517 (17)	0.0367 (16)	0.0026 (14)	0.0039 (13)	0.0020 (13)
C8	0.0249 (14)	0.0190 (13)	0.0358 (16)	−0.0022 (11)	0.0006 (12)	0.0023 (12)
C7	0.0241 (14)	0.0235 (15)	0.0391 (17)	−0.0028 (12)	−0.0003 (13)	0.0033 (12)
C11	0.0254 (15)	0.0275 (15)	0.0359 (18)	−0.0012 (12)	0.0042 (13)	−0.0005 (13)
C5	0.0302 (15)	0.0261 (15)	0.0343 (17)	−0.0044 (12)	0.0012 (13)	−0.0025 (12)
C12	0.0242 (15)	0.0270 (15)	0.0423 (19)	0.0013 (12)	−0.0026 (13)	0.0007 (13)
C9	0.0256 (16)	0.0264 (15)	0.0403 (18)	0.0028 (12)	0.0005 (13)	0.0006 (13)
C6	0.0284 (15)	0.0297 (16)	0.0395 (18)	−0.0001 (13)	−0.0022 (13)	−0.0026 (13)
C13	0.0301 (15)	0.0265 (15)	0.0318 (16)	−0.0019 (12)	−0.0012 (12)	−0.0011 (12)
C10	0.0281 (15)	0.0289 (16)	0.0402 (18)	0.0015 (13)	0.0034 (14)	−0.0034 (13)
C14	0.0347 (16)	0.0382 (17)	0.0339 (17)	0.0054 (15)	−0.0035 (13)	−0.0010 (14)
C4	0.0305 (17)	0.0399 (18)	0.0389 (19)	−0.0029 (14)	0.0036 (14)	−0.0053 (14)
C2	0.0317 (17)	0.0398 (18)	0.0368 (18)	0.0024 (14)	0.0045 (14)	−0.0016 (14)
C3	0.0413 (18)	0.047 (2)	0.040 (2)	−0.0053 (16)	0.0080 (16)	−0.0082 (16)
C1	0.040 (2)	0.048 (2)	0.0395 (19)	0.0042 (15)	−0.0011 (15)	0.0025 (15)
C15	0.059 (3)	0.074 (3)	0.031 (2)	−0.001 (2)	−0.0083 (18)	−0.0095 (19)

Geometric parameters (Å, º)

O2—C13	1.396 (3)	C12—H12	1.00 (4)
O2—C14	1.369 (4)	C9—C10	1.382 (4)
O1—C14	1.198 (3)	C9—H9	1.01 (3)
N1—C3	1.343 (4)	C6—H6	0.91 (4)
N1—C1	1.343 (4)	C13—C10	1.388 (4)
C8—C7	1.461 (4)	C10—H10	0.93 (4)
C8—C11	1.411 (4)	C14—C15	1.482 (5)
C8—C9	1.397 (4)	C4—C3	1.369 (5)
C7—C6	1.326 (4)	C4—H4	0.95 (3)
C7—H7	0.99 (3)	C2—C1	1.374 (4)
C11—C12	1.376 (4)	C2—H2	0.95 (3)
C11—H11	0.94 (3)	C3—H3	0.97 (4)
C5—C6	1.465 (4)	C1—H1	1.00 (3)
C5—C4	1.387 (4)	C15—H15A	0.93 (7)
C5—C2	1.394 (4)	C15—H15B	0.96 (5)
C12—C13	1.383 (4)	C15—H15C	0.96 (6)
C14—O2—C13	119.3 (2)	C10—C13—O2	120.8 (2)
C3—N1—C1	115.2 (3)	C9—C10—C13	118.8 (3)
C11—C8—C7	123.4 (3)	C9—C10—H10	124 (2)
C9—C8—C7	119.1 (3)	C13—C10—H10	117 (2)
C9—C8—C11	117.4 (3)	O2—C14—C15	111.2 (3)
C8—C7—H7	113.9 (16)	O1—C14—O2	122.4 (3)
C6—C7—C8	128.6 (3)	O1—C14—C15	126.3 (3)
C6—C7—H7	117.3 (16)	C5—C4—H4	119.1 (19)
C8—C11—H11	116 (2)	C3—C4—C5	120.5 (3)
C12—C11—C8	121.0 (3)	C3—C4—H4	120.4 (19)
C12—C11—H11	123 (2)	C5—C2—H2	122.0 (19)
C4—C5—C6	120.3 (3)	C1—C2—C5	119.8 (3)
C4—C5—C2	116.0 (3)	C1—C2—H2	118.1 (19)
C2—C5—C6	123.7 (3)	N1—C3—C4	124.1 (3)
C11—C12—C13	119.9 (3)	N1—C3—H3	114 (2)
C11—C12—H12	122.5 (19)	C4—C3—H3	122 (2)
C13—C12—H12	117.4 (19)	N1—C1—C2	124.4 (3)
C8—C9—H9	117.2 (16)	N1—C1—H1	118.7 (19)
C10—C9—C8	122.1 (3)	C2—C1—H1	116.8 (19)
C10—C9—H9	120.7 (16)	C14—C15—H15A	117 (4)
C7—C6—C5	126.3 (3)	C14—C15—H15B	110 (3)
C7—C6—H6	118 (2)	C14—C15—H15C	109 (3)
C5—C6—H6	115 (2)	H15A—C15—H15B	107 (5)
C12—C13—O2	118.2 (2)	H15A—C15—H15C	97 (5)
C12—C13—C10	120.8 (3)	H15B—C15—H15C	116 (4)
O2—C13—C10—C9	−173.2 (2)	C9—C8—C11—C12	0.8 (4)
C8—C7—C6—C5	171.3 (3)	C6—C5—C4—C3	176.2 (3)
C8—C11—C12—C13	0.6 (4)	C6—C5—C2—C1	−176.7 (3)
C8—C9—C10—C13	−0.3 (4)	C13—O2—C14—O1	−8.3 (4)
C7—C8—C11—C12	−176.0 (2)	C13—O2—C14—C15	171.7 (3)
C7—C8—C9—C10	176.0 (3)	C14—O2—C13—C12	121.2 (3)
C11—C8—C7—C6	−1.3 (5)	C14—O2—C13—C10	−63.8 (3)
C11—C8—C9—C10	−1.0 (4)	C4—C5—C6—C7	−168.7 (3)
C11—C12—C13—O2	173.1 (2)	C4—C5—C2—C1	1.0 (4)
C11—C12—C13—C10	−1.9 (4)	C2—C5—C6—C7	8.9 (5)
C5—C4—C3—N1	1.4 (5)	C2—C5—C4—C3	−1.6 (4)
C5—C2—C1—N1	−0.1 (5)	C3—N1—C1—C2	−0.2 (5)
C12—C13—C10—C9	1.7 (4)	C1—N1—C3—C4	−0.4 (5)
C9—C8—C7—C6	−178.1 (3)

(web134)

Crystal data

2(C15H13NO2)·C6H4I2O2	Z = 2
Mr = 840.42	F(000) = 828
Triclinic, P1	Dx = 1.639 Mg m^−3
a = 9.3954 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.055 (2) Å	Cell parameters from 7232 reflections
c = 19.911 (2) Å	θ = 1.0–27.5°
α = 101.278 (5)°	µ = 1.89 mm^−1
β = 92.285 (5)°	T = 293 K
γ = 111.552 (5)°	Plate, colourless
V = 1702.8 (4) Å^3	0.20 × 0.16 × 0.03 mm

Data collection

Nonius Kappa CCD diffractometer	8137 independent reflections
Radiation source: fine-focus sealed tube	4839 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.033
CCD rotation images, phi scans	θmax = 28.0°, θmin = 1.1°
Absorption correction: multi-scan SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1061 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.8044. The λ/2 correction factor is Not present.	h = −12→11
Tmin = 0.702, Tmax = 0.945	k = −13→13
14414 measured reflections	l = −26→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0592P)^2 + 0.1166P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.120	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.80 e Å^−3
8137 reflections	Δρmin = −0.48 e Å^−3
420 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0039 (5)
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.16887 (4)	0.25927 (3)	0.79790 (2)	0.05615 (13)
I2	−0.43848 (3)	0.25478 (4)	0.68172 (2)	0.06009 (13)
O5	0.2177 (3)	0.2583 (4)	0.64224 (16)	0.0676 (9)
H5	0.2376	0.2697	0.6035	0.101*
O4	0.5336 (4)	0.2285 (4)	0.00296 (17)	0.0689 (9)
O6	−0.2722 (4)	0.2324 (5)	0.54844 (16)	0.0708 (10)
H6A	−0.2262	0.2426	0.5145	0.106*
O2	0.8892 (4)	0.2156 (4)	0.06356 (17)	0.0707 (10)
O3	0.3872 (5)	0.2894 (5)	−0.06607 (19)	0.0809 (11)
N2	−0.1349 (5)	0.2402 (5)	0.4305 (2)	0.0646 (11)
O1	1.0634 (5)	0.4441 (5)	0.0996 (3)	0.1037 (14)
N1	0.2945 (5)	0.2587 (6)	0.5142 (2)	0.0722 (13)
C32	0.0733 (5)	0.2514 (5)	0.6495 (2)	0.0489 (10)
C35	−0.2211 (5)	0.2476 (5)	0.6682 (2)	0.0501 (11)
C36	−0.1225 (5)	0.2544 (4)	0.7233 (2)	0.0499 (11)
H36	−0.1545	0.2588	0.7670	0.060*
C31	0.0217 (5)	0.2547 (5)	0.7145 (2)	0.0474 (10)
C8	0.6486 (5)	0.1997 (5)	0.2355 (2)	0.0503 (11)
C5	0.4354 (5)	0.2700 (5)	0.3922 (2)	0.0557 (11)
C34	−0.1749 (5)	0.2403 (5)	0.6019 (2)	0.0540 (11)
C28	0.4338 (5)	0.2222 (6)	0.0541 (2)	0.0566 (12)
C33	−0.0269 (5)	0.2435 (5)	0.5942 (2)	0.0555 (12)
H33	0.0058	0.2403	0.5506	0.067*
C29	0.4991 (6)	0.2646 (5)	−0.0551 (2)	0.0570 (12)
C13	0.8141 (5)	0.2176 (5)	0.1226 (2)	0.0562 (12)
C7	0.5661 (5)	0.1880 (5)	0.2963 (2)	0.0580 (12)
H7	0.5490	0.1037	0.3128	0.070*
C23	0.2557 (6)	0.2027 (6)	0.1627 (2)	0.0605 (12)
C20	0.0329 (5)	0.2629 (5)	0.3166 (2)	0.0555 (12)
C9	0.6857 (5)	0.0829 (5)	0.2027 (3)	0.0619 (12)
H9	0.6549	−0.0029	0.2190	0.074*
C6	0.5133 (5)	0.2827 (6)	0.3304 (2)	0.0593 (12)
H6	0.5269	0.3659	0.3134	0.071*
C12	0.7803 (6)	0.3357 (5)	0.1532 (3)	0.0629 (13)
H12	0.8113	0.4208	0.1365	0.075*
C11	0.6996 (6)	0.3244 (5)	0.2092 (2)	0.0604 (12)
H11	0.6780	0.4047	0.2305	0.072*
C14	1.0103 (6)	0.3359 (7)	0.0565 (3)	0.0715 (15)
C10	0.7678 (5)	0.0924 (5)	0.1463 (3)	0.0613 (12)
H10	0.7910	0.0134	0.1247	0.074*
C27	0.4315 (6)	0.3493 (6)	0.0944 (3)	0.0665 (13)
H27	0.4881	0.4408	0.0859	0.080*
C4	0.3757 (5)	0.3730 (6)	0.4200 (3)	0.0638 (13)
H4	0.3823	0.4491	0.3986	0.077*
C25	0.3481 (6)	0.0886 (6)	0.0660 (3)	0.0707 (14)
H25	0.3484	0.0037	0.0373	0.085*
C3	0.3075 (6)	0.3622 (7)	0.4787 (3)	0.0723 (15)
H3	0.2667	0.4318	0.4955	0.087*
C2	0.4223 (6)	0.1610 (6)	0.4280 (3)	0.0712 (14)
H2	0.4607	0.0891	0.4120	0.085*
C18	−0.0906 (6)	0.3586 (7)	0.4053 (3)	0.0721 (15)
H18	−0.1164	0.4364	0.4262	0.087*
C17	−0.0134 (6)	0.1374 (6)	0.3425 (3)	0.0722 (15)
H17	0.0103	0.0578	0.3222	0.087*
C21	0.1248 (6)	0.2816 (6)	0.2580 (3)	0.0658 (13)
H21	0.1576	0.3733	0.2472	0.079*
C22	0.1638 (6)	0.1848 (6)	0.2206 (3)	0.0674 (14)
H22	0.1303	0.0930	0.2313	0.081*
C1	0.3527 (6)	0.1606 (7)	0.4865 (3)	0.0784 (16)
H1	0.3450	0.0860	0.5092	0.094*
C16	−0.0956 (6)	0.1317 (6)	0.3990 (3)	0.0748 (15)
H16	−0.1250	0.0467	0.4158	0.090*
C26	0.3407 (6)	0.3354 (6)	0.1485 (3)	0.0691 (14)
H26	0.3378	0.4201	0.1762	0.083*
C30	0.6187 (6)	0.2682 (6)	−0.1025 (3)	0.0786 (16)
H30A	0.7142	0.3474	−0.0824	0.118*
H30B	0.5859	0.2824	−0.1459	0.118*
H30C	0.6332	0.1769	−0.1098	0.118*
C19	−0.0076 (6)	0.3744 (6)	0.3493 (3)	0.0682 (14)
H19	0.0205	0.4611	0.3338	0.082*
C24	0.2606 (7)	0.0782 (6)	0.1202 (3)	0.0769 (15)
H24	0.2042	−0.0136	0.1283	0.092*
C15	1.0673 (7)	0.3074 (8)	−0.0112 (3)	0.106 (2)
H15A	1.0722	0.2119	−0.0201	0.159*
H15B	1.1683	0.3804	−0.0103	0.159*
H15C	0.9983	0.3114	−0.0469	0.159*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0665 (2)	0.0636 (2)	0.0466 (2)	0.03351 (17)	0.00496 (14)	0.01470 (15)
I2	0.0516 (2)	0.0806 (3)	0.0597 (2)	0.03340 (17)	0.02117 (14)	0.02343 (17)
O5	0.0546 (19)	0.114 (3)	0.052 (2)	0.0481 (19)	0.0198 (15)	0.026 (2)
O4	0.072 (2)	0.103 (3)	0.053 (2)	0.051 (2)	0.0222 (17)	0.0282 (19)
O6	0.0572 (19)	0.122 (3)	0.0431 (19)	0.042 (2)	0.0108 (15)	0.025 (2)
O2	0.068 (2)	0.083 (2)	0.056 (2)	0.025 (2)	0.0269 (17)	0.0075 (18)
O3	0.082 (3)	0.120 (3)	0.063 (2)	0.053 (2)	0.0175 (19)	0.043 (2)
N2	0.062 (3)	0.087 (3)	0.048 (2)	0.031 (2)	0.0154 (19)	0.016 (2)
O1	0.078 (3)	0.089 (3)	0.119 (4)	0.008 (2)	0.044 (3)	0.010 (3)
N1	0.058 (3)	0.113 (4)	0.047 (2)	0.035 (3)	0.018 (2)	0.015 (3)
C32	0.049 (2)	0.059 (3)	0.048 (3)	0.030 (2)	0.013 (2)	0.016 (2)
C35	0.041 (2)	0.066 (3)	0.050 (3)	0.026 (2)	0.0158 (19)	0.016 (2)
C36	0.057 (3)	0.065 (3)	0.042 (2)	0.034 (2)	0.018 (2)	0.017 (2)
C31	0.050 (2)	0.052 (3)	0.043 (2)	0.022 (2)	0.0088 (19)	0.012 (2)
C8	0.046 (2)	0.060 (3)	0.044 (2)	0.021 (2)	0.0040 (19)	0.010 (2)
C5	0.048 (3)	0.069 (3)	0.049 (3)	0.019 (2)	0.010 (2)	0.014 (2)
C34	0.052 (3)	0.074 (3)	0.042 (2)	0.032 (2)	0.012 (2)	0.014 (2)
C28	0.063 (3)	0.082 (4)	0.041 (3)	0.042 (3)	0.015 (2)	0.021 (2)
C33	0.056 (3)	0.076 (3)	0.040 (2)	0.032 (2)	0.019 (2)	0.011 (2)
C29	0.065 (3)	0.057 (3)	0.047 (3)	0.020 (2)	0.013 (2)	0.015 (2)
C13	0.054 (3)	0.067 (3)	0.047 (3)	0.024 (2)	0.010 (2)	0.007 (2)
C7	0.053 (3)	0.065 (3)	0.054 (3)	0.018 (2)	0.009 (2)	0.019 (2)
C23	0.060 (3)	0.076 (4)	0.050 (3)	0.028 (3)	0.013 (2)	0.018 (3)
C20	0.050 (3)	0.069 (3)	0.037 (2)	0.012 (2)	0.004 (2)	0.008 (2)
C9	0.063 (3)	0.058 (3)	0.066 (3)	0.021 (2)	0.013 (2)	0.021 (3)
C6	0.062 (3)	0.075 (3)	0.051 (3)	0.032 (3)	0.017 (2)	0.023 (2)
C12	0.074 (3)	0.059 (3)	0.065 (3)	0.030 (3)	0.027 (3)	0.022 (2)
C11	0.070 (3)	0.064 (3)	0.056 (3)	0.035 (3)	0.021 (2)	0.015 (2)
C14	0.057 (3)	0.096 (4)	0.069 (4)	0.033 (3)	0.024 (3)	0.025 (3)
C10	0.062 (3)	0.060 (3)	0.062 (3)	0.026 (2)	0.013 (2)	0.009 (3)
C27	0.077 (3)	0.067 (3)	0.064 (3)	0.031 (3)	0.021 (3)	0.022 (3)
C4	0.059 (3)	0.078 (3)	0.057 (3)	0.029 (3)	0.010 (2)	0.016 (3)
C25	0.091 (4)	0.071 (4)	0.056 (3)	0.039 (3)	0.020 (3)	0.011 (3)
C3	0.055 (3)	0.105 (4)	0.058 (3)	0.037 (3)	0.011 (2)	0.008 (3)
C2	0.082 (4)	0.093 (4)	0.053 (3)	0.043 (3)	0.029 (3)	0.028 (3)
C18	0.084 (4)	0.085 (4)	0.056 (3)	0.048 (3)	0.010 (3)	0.006 (3)
C17	0.082 (4)	0.077 (4)	0.052 (3)	0.028 (3)	0.022 (3)	0.004 (3)
C21	0.065 (3)	0.073 (3)	0.053 (3)	0.020 (3)	0.008 (2)	0.012 (3)
C22	0.068 (3)	0.069 (3)	0.062 (3)	0.025 (3)	0.007 (3)	0.010 (3)
C1	0.080 (4)	0.102 (4)	0.062 (3)	0.034 (3)	0.023 (3)	0.035 (3)
C16	0.087 (4)	0.067 (3)	0.066 (4)	0.020 (3)	0.023 (3)	0.023 (3)
C26	0.082 (4)	0.076 (4)	0.055 (3)	0.043 (3)	0.011 (3)	0.002 (3)
C30	0.083 (4)	0.093 (4)	0.067 (4)	0.033 (3)	0.031 (3)	0.031 (3)
C19	0.076 (3)	0.077 (4)	0.056 (3)	0.031 (3)	0.017 (3)	0.019 (3)
C24	0.089 (4)	0.074 (4)	0.062 (3)	0.024 (3)	0.026 (3)	0.012 (3)
C15	0.084 (4)	0.167 (7)	0.077 (4)	0.050 (4)	0.043 (3)	0.037 (4)

Geometric parameters (Å, º)

I1—C31	2.100 (4)	C23—C24	1.384 (7)
I2—C35	2.097 (4)	C20—C17	1.384 (7)
O5—H5	0.8200	C20—C21	1.481 (7)
O5—C32	1.348 (5)	C20—C19	1.369 (7)
O4—C28	1.406 (5)	C9—H9	0.9300
O4—C29	1.340 (6)	C9—C10	1.388 (7)
O6—H6A	0.8200	C6—H6	0.9300
O6—C34	1.346 (5)	C12—H12	0.9300
O2—C13	1.396 (5)	C12—C11	1.373 (7)
O2—C14	1.359 (7)	C11—H11	0.9300
O3—C29	1.188 (6)	C14—C15	1.484 (8)
N2—C18	1.315 (7)	C10—H10	0.9300
N2—C16	1.330 (6)	C27—H27	0.9300
O1—C14	1.171 (6)	C27—C26	1.396 (7)
N1—C3	1.342 (7)	C4—H4	0.9300
N1—C1	1.335 (7)	C4—C3	1.358 (7)
C32—C31	1.398 (6)	C25—H25	0.9300
C32—C33	1.391 (6)	C25—C24	1.381 (7)
C35—C36	1.381 (6)	C3—H3	0.9300
C35—C34	1.402 (6)	C2—H2	0.9300
C36—H36	0.9300	C2—C1	1.359 (7)
C36—C31	1.372 (5)	C18—H18	0.9300
C8—C7	1.463 (6)	C18—C19	1.387 (7)
C8—C9	1.395 (6)	C17—H17	0.9300
C8—C11	1.384 (6)	C17—C16	1.388 (7)
C5—C6	1.459 (6)	C21—H21	0.9300
C5—C4	1.387 (7)	C21—C22	1.279 (7)
C5—C2	1.392 (7)	C22—H22	0.9300
C34—C33	1.394 (6)	C1—H1	0.9300
C28—C27	1.379 (6)	C16—H16	0.9300
C28—C25	1.362 (7)	C26—H26	0.9300
C33—H33	0.9300	C30—H30A	0.9600
C29—C30	1.492 (7)	C30—H30B	0.9600
C13—C12	1.375 (6)	C30—H30C	0.9600
C13—C10	1.357 (7)	C19—H19	0.9300
C7—H7	0.9300	C24—H24	0.9300
C7—C6	1.318 (6)	C15—H15A	0.9600
C23—C22	1.468 (7)	C15—H15B	0.9600
C23—C26	1.371 (7)	C15—H15C	0.9600
C32—O5—H5	109.5	O2—C14—C15	110.6 (5)
C29—O4—C28	118.4 (4)	O1—C14—O2	123.5 (5)
C34—O6—H6A	109.5	O1—C14—C15	125.9 (6)
C14—O2—C13	120.9 (4)	C13—C10—C9	119.7 (4)
C18—N2—C16	116.0 (5)	C13—C10—H10	120.1
C1—N1—C3	114.5 (5)	C9—C10—H10	120.1
O5—C32—C31	119.8 (4)	C28—C27—H27	121.3
O5—C32—C33	121.9 (4)	C28—C27—C26	117.3 (5)
C33—C32—C31	118.3 (4)	C26—C27—H27	121.3
C36—C35—I2	121.3 (3)	C5—C4—H4	120.2
C36—C35—C34	120.2 (4)	C3—C4—C5	119.6 (5)
C34—C35—I2	118.5 (3)	C3—C4—H4	120.2
C35—C36—H36	119.5	C28—C25—H25	119.8
C31—C36—C35	121.0 (4)	C28—C25—C24	120.5 (5)
C31—C36—H36	119.5	C24—C25—H25	119.8
C32—C31—I1	118.7 (3)	N1—C3—C4	125.0 (5)
C36—C31—I1	120.9 (3)	N1—C3—H3	117.5
C36—C31—C32	120.4 (4)	C4—C3—H3	117.5
C9—C8—C7	119.8 (4)	C5—C2—H2	120.3
C11—C8—C7	123.7 (4)	C1—C2—C5	119.3 (5)
C11—C8—C9	116.4 (4)	C1—C2—H2	120.3
C4—C5—C6	120.2 (5)	N2—C18—H18	118.0
C4—C5—C2	116.4 (5)	N2—C18—C19	124.0 (5)
C2—C5—C6	123.3 (4)	C19—C18—H18	118.0
O6—C34—C35	119.7 (4)	C20—C17—H17	120.4
O6—C34—C33	122.3 (4)	C20—C17—C16	119.2 (5)
C33—C34—C35	118.0 (4)	C16—C17—H17	120.4
C27—C28—O4	120.5 (5)	C20—C21—H21	116.6
C25—C28—O4	118.4 (4)	C22—C21—C20	126.8 (5)
C25—C28—C27	120.9 (5)	C22—C21—H21	116.6
C32—C33—C34	122.1 (4)	C23—C22—H22	116.5
C32—C33—H33	119.0	C21—C22—C23	127.1 (5)
C34—C33—H33	119.0	C21—C22—H22	116.5
O4—C29—C30	110.8 (4)	N1—C1—C2	125.2 (6)
O3—C29—O4	123.3 (5)	N1—C1—H1	117.4
O3—C29—C30	125.9 (5)	C2—C1—H1	117.4
C12—C13—O2	122.5 (5)	N2—C16—C17	124.1 (5)
C10—C13—O2	116.1 (4)	N2—C16—H16	118.0
C10—C13—C12	121.3 (5)	C17—C16—H16	118.0
C8—C7—H7	116.2	C23—C26—C27	123.1 (5)
C6—C7—C8	127.7 (5)	C23—C26—H26	118.4
C6—C7—H7	116.2	C27—C26—H26	118.4
C26—C23—C22	124.4 (5)	C29—C30—H30A	109.5
C26—C23—C24	117.3 (5)	C29—C30—H30B	109.5
C24—C23—C22	118.2 (5)	C29—C30—H30C	109.5
C17—C20—C21	123.4 (5)	H30A—C30—H30B	109.5
C19—C20—C17	116.5 (5)	H30A—C30—H30C	109.5
C19—C20—C21	120.0 (5)	H30B—C30—H30C	109.5
C8—C9—H9	119.5	C20—C19—C18	120.2 (5)
C10—C9—C8	121.1 (5)	C20—C19—H19	119.9
C10—C9—H9	119.5	C18—C19—H19	119.9
C5—C6—H6	116.8	C23—C24—H24	119.6
C7—C6—C5	126.4 (5)	C25—C24—C23	120.8 (5)
C7—C6—H6	116.8	C25—C24—H24	119.6
C13—C12—H12	120.9	C14—C15—H15A	109.5
C11—C12—C13	118.2 (5)	C14—C15—H15B	109.5
C11—C12—H12	120.9	C14—C15—H15C	109.5
C8—C11—H11	118.4	H15A—C15—H15B	109.5
C12—C11—C8	123.3 (4)	H15A—C15—H15C	109.5
C12—C11—H11	118.4	H15B—C15—H15C	109.5
I2—C35—C36—C31	−177.7 (3)	C7—C8—C11—C12	178.3 (5)
I2—C35—C34—O6	−2.6 (6)	C20—C17—C16—N2	0.5 (8)
I2—C35—C34—C33	176.6 (3)	C20—C21—C22—C23	−179.6 (4)
O5—C32—C31—I1	−3.2 (6)	C9—C8—C7—C6	−175.0 (5)
O5—C32—C31—C36	177.1 (4)	C9—C8—C11—C12	1.0 (7)
O5—C32—C33—C34	−178.2 (4)	C6—C5—C4—C3	−178.1 (4)
O4—C28—C27—C26	−173.9 (4)	C6—C5—C2—C1	177.6 (5)
O4—C28—C25—C24	173.3 (5)	C12—C13—C10—C9	−0.5 (7)
O6—C34—C33—C32	−179.9 (5)	C11—C8—C7—C6	7.9 (7)
O2—C13—C12—C11	176.9 (4)	C11—C8—C9—C10	−0.8 (7)
O2—C13—C10—C9	−176.9 (4)	C14—O2—C13—C12	41.8 (7)
N2—C18—C19—C20	0.1 (8)	C14—O2—C13—C10	−141.9 (5)
C35—C36—C31—I1	−178.3 (3)	C10—C13—C12—C11	0.8 (7)
C35—C36—C31—C32	1.4 (7)	C27—C28—C25—C24	−2.1 (8)
C35—C34—C33—C32	0.9 (7)	C4—C5—C6—C7	−175.3 (5)
C36—C35—C34—O6	179.4 (4)	C4—C5—C2—C1	0.4 (7)
C36—C35—C34—C33	−1.4 (7)	C25—C28—C27—C26	1.4 (7)
C31—C32—C33—C34	0.6 (7)	C3—N1—C1—C2	0.8 (8)
C8—C7—C6—C5	−178.0 (4)	C2—C5—C6—C7	7.5 (8)
C8—C9—C10—C13	0.5 (7)	C2—C5—C4—C3	−0.8 (7)
C5—C4—C3—N1	1.3 (8)	C18—N2—C16—C17	−0.3 (8)
C5—C2—C1—N1	−0.4 (9)	C17—C20—C21—C22	5.5 (8)
C34—C35—C36—C31	0.2 (7)	C17—C20—C19—C18	0.1 (7)
C28—O4—C29—O3	−1.2 (7)	C21—C20—C17—C16	178.1 (5)
C28—O4—C29—C30	179.0 (4)	C21—C20—C19—C18	−178.4 (4)
C28—C27—C26—C23	0.0 (8)	C22—C23—C26—C27	177.6 (5)
C28—C25—C24—C23	1.3 (8)	C22—C23—C24—C25	−178.4 (5)
C33—C32—C31—I1	177.9 (3)	C1—N1—C3—C4	−1.2 (8)
C33—C32—C31—C36	−1.8 (7)	C16—N2—C18—C19	0.0 (8)
C29—O4—C28—C27	−74.1 (6)	C26—C23—C22—C21	14.1 (8)
C29—O4—C28—C25	110.5 (5)	C26—C23—C24—C25	0.1 (8)
C13—O2—C14—O1	3.8 (8)	C19—C20—C17—C16	−0.3 (7)
C13—O2—C14—C15	−178.6 (5)	C19—C20—C21—C22	−176.1 (5)
C13—C12—C11—C8	−1.1 (8)	C24—C23—C22—C21	−167.6 (5)
C7—C8—C9—C10	−178.1 (4)	C24—C23—C26—C27	−0.7 (8)

(web006)

Crystal data

C30H26N2O4·C6H4I2O2	F(000) = 1656
Mr = 840.42	Dx = 1.637 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 1.2399 Å
a = 21.7663 (10) Å	Cell parameters from 6743 reflections
b = 9.8526 (5) Å	θ = 3.5–49.2°
c = 16.2690 (7) Å	µ = 8.37 mm^−1
β = 102.198 (2)°	T = 150 K
V = 3410.2 (3) Å^3	Block, colorless
Z = 4	0.10 × 0.08 × 0.05 mm

Data collection

Bruker D8 diffractometer	6120 independent reflections
Radiation source: synchrotron, Bend magnet, Station 11.3.1, ALS, LBNL	5506 reflections with I > 2σ(I)
Silicon 111 monochromator	Rint = 0.055
ω rotation scans	θmax = 48.1°, θmin = 4.0°
Absorption correction: multi-scan SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1061 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.8044. The λ/2 correction factor is Not present.	h = −26→26
Tmin = 0.470, Tmax = 0.658	k = −11→11
23281 measured reflections	l = −19→19

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1005P)^2 + 14.9743P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6120 reflections	Δρmax = 2.43 e Å^−3
395 parameters	Δρmin = −1.87 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I2	0.74864 (2)	0.57795 (5)	0.28461 (3)	0.04173 (17)
I1	0.64417 (2)	0.87199 (4)	−0.03725 (3)	0.04109 (17)
O6	0.60466 (19)	0.5066 (5)	0.2604 (3)	0.0344 (9)
H6A	0.5672	0.4807	0.2536	0.052*
O5	0.5198 (2)	0.7509 (5)	0.0048 (3)	0.0410 (10)
H5	0.4858	0.7307	0.0182	0.062*
N1	0.4041 (2)	0.6970 (5)	0.0327 (3)	0.0332 (11)
N2	0.4879 (2)	0.4789 (6)	0.2831 (3)	0.0356 (11)
C36	0.6801 (3)	0.7081 (6)	0.1223 (4)	0.0306 (12)
H36	0.7213	0.7354	0.1185	0.037*
C32	0.5681 (3)	0.7100 (6)	0.0656 (4)	0.0307 (12)
C4	0.3418 (3)	0.7290 (6)	0.1363 (4)	0.0330 (12)
H4	0.3333	0.7811	0.1818	0.040*
C35	0.6712 (3)	0.6271 (6)	0.1883 (4)	0.0284 (12)
C31	0.6289 (3)	0.7491 (6)	0.0617 (3)	0.0298 (12)
C3	0.3905 (3)	0.7641 (6)	0.0992 (4)	0.0333 (13)
H3	0.4160	0.8394	0.1212	0.040*
C5	0.3044 (3)	0.6152 (6)	0.1068 (4)	0.0344 (13)
O2	−0.0500 (4)	0.6232 (9)	0.1021 (6)	0.1040 (14)
C34	0.6112 (3)	0.5856 (6)	0.1951 (4)	0.0290 (12)
C33	0.5599 (3)	0.6264 (6)	0.1329 (4)	0.0306 (12)
H33	0.5188	0.5973	0.1360	0.037*
C18	0.4623 (3)	0.5551 (7)	0.3351 (4)	0.0396 (15)
H18	0.4891	0.6070	0.3772	0.047*
C1	0.3661 (3)	0.5945 (7)	0.0016 (4)	0.0369 (14)
H1	0.3731	0.5493	−0.0471	0.044*
C20	0.3581 (3)	0.4860 (6)	0.2687 (4)	0.0375 (14)
C17	0.3850 (3)	0.4033 (7)	0.2191 (4)	0.0387 (14)
H17	0.3594	0.3461	0.1789	0.046*
C19	0.3976 (3)	0.5607 (7)	0.3297 (4)	0.0406 (15)
H19	0.3809	0.6157	0.3676	0.049*
C2	0.3172 (3)	0.5510 (6)	0.0365 (4)	0.0355 (13)
H2	0.2921	0.4765	0.0122	0.043*
C23	0.2150 (3)	0.5721 (7)	0.3490 (4)	0.0413 (15)
C16	0.4491 (3)	0.4026 (7)	0.2273 (4)	0.0375 (14)
H16	0.4667	0.3450	0.1915	0.045*
C6	0.2573 (3)	0.5543 (6)	0.1533 (4)	0.0375 (14)
H6	0.2303	0.4846	0.1182	0.045*
C21	0.2860 (3)	0.4983 (6)	0.2447 (4)	0.0357 (13)
H21	0.2666	0.4084	0.2523	0.043*
C24	0.1746 (3)	0.4606 (8)	0.3380 (5)	0.0467 (16)
H24	0.1732	0.4031	0.2907	0.056*
C22	0.2525 (3)	0.6108 (7)	0.2850 (4)	0.0385 (15)
H22	0.2838	0.6821	0.3093	0.046*
C7	0.2169 (3)	0.6561 (7)	0.1926 (4)	0.0394 (14)
H7	0.2287	0.7514	0.1814	0.047*
C8	0.1460 (3)	0.6391 (7)	0.1688 (4)	0.0407 (15)
O3	0.1355 (4)	0.2929 (10)	0.5573 (6)	0.1040 (14)
C26	0.2166 (4)	0.6501 (9)	0.4199 (5)	0.0529 (18)
H26	0.2437	0.7267	0.4296	0.063*
C25	0.1363 (4)	0.4314 (9)	0.3944 (6)	0.060 (2)
H25	0.1084	0.3562	0.3849	0.072*
C9	0.1161 (3)	0.5309 (9)	0.1229 (5)	0.0524 (18)
H9	0.1405	0.4621	0.1042	0.063*
C11	0.1090 (4)	0.7363 (9)	0.1956 (6)	0.061 (2)
H11	0.1287	0.8109	0.2277	0.073*
C28	0.1395 (5)	0.5133 (10)	0.4646 (6)	0.070 (3)
C27	0.1795 (6)	0.6196 (9)	0.4777 (6)	0.070 (3)
H27	0.1825	0.6739	0.5266	0.084*
C10	0.0505 (4)	0.5210 (10)	0.1036 (5)	0.058 (2)
H10	0.0306	0.4447	0.0736	0.070*
C13	0.0152 (3)	0.6223 (8)	0.1283 (5)	0.0520 (19)
C15	−0.1511 (5)	0.5376 (14)	0.0945 (9)	0.094 (3)
H15A	−0.1606	0.6177	0.0583	0.141*
H15B	−0.1746	0.5426	0.1396	0.141*
H15C	−0.1633	0.4555	0.0611	0.141*
C14	−0.0847 (4)	0.5335 (10)	0.1306 (6)	0.066 (2)
C12	0.0447 (4)	0.7285 (10)	0.1775 (7)	0.069 (3)
H12	0.0204	0.7952	0.1984	0.083*
C29	0.0975 (6)	0.3787 (9)	0.5597 (7)	0.088 (3)
O1	−0.0594 (4)	0.4621 (9)	0.1865 (6)	0.1040 (14)
C30	0.0486 (6)	0.3781 (14)	0.6092 (9)	0.094 (3)
H30A	0.0077	0.3609	0.5720	0.141*
H30B	0.0477	0.4664	0.6367	0.141*
H30C	0.0576	0.3068	0.6520	0.141*
O4	0.0983 (4)	0.4925 (9)	0.5183 (6)	0.1040 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I2	0.0284 (2)	0.0559 (3)	0.0400 (3)	0.00555 (16)	0.00522 (17)	0.01099 (18)
I1	0.0483 (3)	0.0391 (3)	0.0376 (3)	−0.00481 (17)	0.01293 (19)	0.00959 (16)
O6	0.027 (2)	0.044 (2)	0.033 (2)	0.0039 (18)	0.0064 (16)	0.0123 (18)
O5	0.034 (2)	0.056 (3)	0.033 (2)	0.003 (2)	0.0044 (18)	0.015 (2)
N1	0.033 (3)	0.034 (3)	0.033 (3)	0.003 (2)	0.005 (2)	0.002 (2)
N2	0.030 (3)	0.039 (3)	0.038 (3)	0.002 (2)	0.008 (2)	0.006 (2)
C36	0.034 (3)	0.026 (3)	0.033 (3)	−0.002 (2)	0.012 (2)	−0.003 (2)
C32	0.034 (3)	0.030 (3)	0.028 (3)	0.003 (2)	0.007 (2)	0.000 (2)
C4	0.033 (3)	0.036 (3)	0.031 (3)	0.005 (2)	0.007 (2)	−0.003 (2)
C35	0.031 (3)	0.028 (3)	0.026 (3)	0.003 (2)	0.004 (2)	−0.002 (2)
C31	0.039 (3)	0.025 (3)	0.027 (3)	−0.001 (2)	0.011 (2)	0.002 (2)
C3	0.032 (3)	0.029 (3)	0.037 (3)	−0.004 (2)	0.003 (2)	0.001 (2)
C5	0.027 (3)	0.034 (3)	0.042 (3)	0.000 (2)	0.007 (2)	0.000 (3)
O2	0.082 (3)	0.109 (3)	0.124 (4)	−0.011 (2)	0.029 (2)	0.037 (3)
C34	0.034 (3)	0.028 (3)	0.027 (3)	0.003 (2)	0.010 (2)	0.001 (2)
C33	0.028 (3)	0.033 (3)	0.031 (3)	0.002 (2)	0.007 (2)	0.002 (2)
C18	0.040 (4)	0.043 (4)	0.033 (3)	−0.001 (3)	0.002 (3)	0.006 (3)
C1	0.042 (4)	0.033 (3)	0.035 (3)	0.006 (3)	0.007 (3)	−0.005 (3)
C20	0.032 (3)	0.032 (3)	0.047 (4)	0.000 (2)	0.006 (3)	0.017 (3)
C17	0.038 (3)	0.034 (3)	0.042 (3)	−0.001 (3)	0.004 (3)	0.008 (3)
C19	0.042 (4)	0.043 (4)	0.040 (3)	0.010 (3)	0.016 (3)	0.006 (3)
C2	0.027 (3)	0.033 (3)	0.044 (3)	−0.001 (2)	0.002 (3)	−0.006 (3)
C23	0.031 (3)	0.045 (4)	0.046 (4)	0.005 (3)	0.006 (3)	−0.001 (3)
C16	0.042 (4)	0.033 (3)	0.039 (3)	0.002 (3)	0.011 (3)	0.003 (3)
C6	0.035 (3)	0.031 (3)	0.046 (4)	0.001 (3)	0.008 (3)	−0.004 (3)
C21	0.032 (3)	0.031 (3)	0.044 (3)	−0.005 (2)	0.008 (3)	−0.001 (3)
C24	0.046 (4)	0.045 (4)	0.052 (4)	0.001 (3)	0.016 (3)	−0.003 (3)
C22	0.033 (3)	0.038 (3)	0.044 (4)	−0.003 (3)	0.007 (3)	−0.006 (3)
C7	0.040 (4)	0.031 (3)	0.050 (4)	0.000 (3)	0.014 (3)	−0.003 (3)
C8	0.033 (3)	0.043 (4)	0.045 (4)	−0.001 (3)	0.005 (3)	−0.001 (3)
O3	0.082 (3)	0.109 (3)	0.124 (4)	−0.011 (2)	0.029 (2)	0.037 (3)
C26	0.048 (4)	0.055 (4)	0.058 (5)	−0.004 (3)	0.018 (3)	−0.008 (4)
C25	0.057 (5)	0.053 (5)	0.079 (6)	−0.010 (4)	0.029 (4)	0.003 (4)
C9	0.038 (4)	0.062 (5)	0.059 (4)	0.003 (3)	0.014 (3)	−0.016 (4)
C11	0.042 (4)	0.050 (4)	0.089 (6)	0.002 (3)	0.010 (4)	−0.018 (4)
C28	0.084 (7)	0.062 (6)	0.081 (6)	−0.004 (5)	0.053 (6)	0.000 (5)
C27	0.106 (8)	0.054 (5)	0.057 (5)	−0.004 (5)	0.033 (5)	−0.010 (4)
C10	0.041 (4)	0.070 (5)	0.060 (5)	−0.004 (4)	0.002 (3)	−0.011 (4)
C13	0.025 (3)	0.063 (5)	0.065 (5)	0.003 (3)	0.002 (3)	0.009 (4)
C15	0.076 (5)	0.107 (6)	0.113 (7)	−0.011 (5)	0.050 (5)	0.000 (5)
C14	0.051 (5)	0.079 (6)	0.069 (5)	0.000 (4)	0.014 (4)	0.028 (5)
C12	0.035 (4)	0.059 (5)	0.117 (8)	0.002 (4)	0.023 (4)	−0.020 (5)
C29	0.123 (10)	0.069 (7)	0.081 (7)	−0.014 (6)	0.044 (7)	0.004 (5)
O1	0.082 (3)	0.109 (3)	0.124 (4)	−0.011 (2)	0.029 (2)	0.037 (3)
C30	0.076 (5)	0.107 (6)	0.113 (7)	−0.011 (5)	0.050 (5)	0.000 (5)
O4	0.082 (3)	0.109 (3)	0.124 (4)	−0.011 (2)	0.029 (2)	0.037 (3)

Geometric parameters (Å, º)

I2—C35	2.101 (6)	C16—H16	0.9500
I1—C31	2.097 (5)	C6—C7	1.557 (9)
O6—C34	1.347 (7)	C6—C21	1.585 (9)
O6—H6A	0.8400	C6—H6	1.0000
O5—C32	1.343 (7)	C21—C22	1.546 (9)
O5—H5	0.8400	C21—H21	1.0000
N1—C1	1.336 (8)	C24—C25	1.394 (11)
N1—C3	1.351 (8)	C24—H24	0.9500
N2—C16	1.333 (9)	C22—C7	1.603 (10)
N2—C18	1.338 (9)	C22—H22	1.0000
C36—C31	1.384 (8)	C7—C8	1.519 (9)
C36—C35	1.385 (8)	C7—H7	1.0000
C36—H36	0.9500	C8—C11	1.381 (10)
C32—C31	1.393 (8)	C8—C9	1.383 (10)
C32—C33	1.412 (8)	O3—C29	1.188 (9)
C4—C3	1.372 (9)	C26—C27	1.395 (12)
C4—C5	1.408 (9)	C26—H26	0.9500
C4—H4	0.9500	C25—C28	1.389 (13)
C35—C34	1.396 (9)	C25—H25	0.9500
C3—H3	0.9500	C9—C10	1.399 (11)
C5—C2	1.387 (9)	C9—H9	0.9500
C5—C6	1.520 (9)	C11—C12	1.370 (11)
O2—C14	1.310 (9)	C11—H11	0.9500
O2—C13	1.392 (11)	C28—C27	1.349 (14)
C34—C33	1.399 (8)	C28—O4	1.394 (11)
C33—H33	0.9500	C27—H27	0.9500
C18—C19	1.393 (10)	C10—C13	1.370 (12)
C18—H18	0.9500	C10—H10	0.9500
C1—C2	1.375 (9)	C13—C12	1.389 (12)
C1—H1	0.9500	C15—C14	1.442 (14)
C20—C17	1.363 (10)	C15—H15A	0.9800
C20—C19	1.380 (10)	C15—H15B	0.9800
C20—C21	1.540 (9)	C15—H15C	0.9800
C17—C16	1.374 (10)	C14—O1	1.188 (9)
C17—H17	0.9500	C12—H12	0.9500
C19—H19	0.9500	C29—O4	1.310 (9)
C2—H2	0.9500	C29—C30	1.465 (12)
C23—C26	1.380 (11)	C30—H30A	0.9800
C23—C24	1.394 (10)	C30—H30B	0.9800
C23—C22	1.502 (10)	C30—H30C	0.9800
C34—O6—H6A	109.5	C22—C21—H21	109.4
C32—O5—H5	109.5	C6—C21—H21	109.4
C1—N1—C3	116.7 (5)	C25—C24—C23	121.7 (7)
C16—N2—C18	117.3 (6)	C25—C24—H24	119.1
C31—C36—C35	119.8 (5)	C23—C24—H24	119.1
C31—C36—H36	120.1	C23—C22—C21	119.1 (6)
C35—C36—H36	120.1	C23—C22—C7	119.7 (5)
O5—C32—C31	119.2 (5)	C21—C22—C7	88.8 (5)
O5—C32—C33	122.6 (5)	C23—C22—H22	109.2
C31—C32—C33	118.2 (5)	C21—C22—H22	109.2
C3—C4—C5	119.7 (6)	C7—C22—H22	109.2
C3—C4—H4	120.1	C8—C7—C6	117.1 (6)
C5—C4—H4	120.1	C8—C7—C22	118.2 (6)
C36—C35—C34	121.2 (5)	C6—C7—C22	90.1 (5)
C36—C35—I2	119.3 (4)	C8—C7—H7	110.0
C34—C35—I2	119.4 (4)	C6—C7—H7	110.0
C36—C31—C32	121.3 (5)	C22—C7—H7	110.0
C36—C31—I1	118.7 (4)	C11—C8—C9	117.7 (7)
C32—C31—I1	120.0 (4)	C11—C8—C7	118.3 (6)
N1—C3—C4	123.3 (6)	C9—C8—C7	124.1 (6)
N1—C3—H3	118.4	C23—C26—C27	121.8 (8)
C4—C3—H3	118.4	C23—C26—H26	119.1
C2—C5—C4	116.2 (6)	C27—C26—H26	119.1
C2—C5—C6	120.4 (6)	C28—C25—C24	119.3 (8)
C4—C5—C6	123.1 (6)	C28—C25—H25	120.4
C14—O2—C13	120.9 (8)	C24—C25—H25	120.4
O6—C34—C35	119.2 (5)	C8—C9—C10	121.1 (7)
O6—C34—C33	122.4 (5)	C8—C9—H9	119.4
C35—C34—C33	118.4 (5)	C10—C9—H9	119.4
C34—C33—C32	121.2 (5)	C12—C11—C8	122.2 (8)
C34—C33—H33	119.4	C12—C11—H11	118.9
C32—C33—H33	119.4	C8—C11—H11	118.9
N2—C18—C19	122.2 (6)	C27—C28—C25	120.0 (8)
N2—C18—H18	118.9	C27—C28—O4	119.6 (9)
C19—C18—H18	118.9	C25—C28—O4	120.2 (9)
N1—C1—C2	123.5 (6)	C28—C27—C26	120.4 (8)
N1—C1—H1	118.3	C28—C27—H27	119.8
C2—C1—H1	118.3	C26—C27—H27	119.8
C17—C20—C19	117.6 (6)	C13—C10—C9	119.5 (8)
C17—C20—C21	116.0 (6)	C13—C10—H10	120.2
C19—C20—C21	126.1 (6)	C9—C10—H10	120.2
C20—C17—C16	120.0 (6)	C10—C13—C12	119.9 (7)
C20—C17—H17	120.0	C10—C13—O2	120.8 (8)
C16—C17—H17	120.0	C12—C13—O2	119.3 (8)
C20—C19—C18	119.6 (6)	C14—C15—H15A	109.5
C20—C19—H19	120.2	C14—C15—H15B	109.5
C18—C19—H19	120.2	H15A—C15—H15B	109.5
C1—C2—C5	120.4 (6)	C14—C15—H15C	109.5
C1—C2—H2	119.8	H15A—C15—H15C	109.5
C5—C2—H2	119.8	H15B—C15—H15C	109.5
C26—C23—C24	116.8 (7)	O1—C14—O2	117.5 (8)
C26—C23—C22	121.1 (6)	O1—C14—C15	126.2 (9)
C24—C23—C22	122.0 (6)	O2—C14—C15	116.1 (9)
N2—C16—C17	123.2 (6)	C11—C12—C13	119.5 (8)
N2—C16—H16	118.4	C11—C12—H12	120.3
C17—C16—H16	118.4	C13—C12—H12	120.3
C5—C6—C7	116.7 (5)	O3—C29—O4	120.5 (10)
C5—C6—C21	115.5 (5)	O3—C29—C30	127.4 (10)
C7—C6—C21	89.1 (5)	O4—C29—C30	112.0 (10)
C5—C6—H6	111.3	C29—C30—H30A	109.5
C7—C6—H6	111.3	C29—C30—H30B	109.5
C21—C6—H6	111.3	H30A—C30—H30B	109.5
C20—C21—C22	119.6 (5)	C29—C30—H30C	109.5
C20—C21—C6	116.4 (5)	H30A—C30—H30C	109.5
C22—C21—C6	91.2 (5)	H30B—C30—H30C	109.5
C20—C21—H21	109.4	C29—O4—C28	121.9 (9)
C31—C36—C35—C34	0.0 (8)	C26—C23—C22—C21	139.8 (7)
C31—C36—C35—I2	−175.3 (4)	C24—C23—C22—C21	−43.5 (9)
C35—C36—C31—C32	−0.3 (9)	C26—C23—C22—C7	−113.4 (8)
C35—C36—C31—I1	179.9 (4)	C24—C23—C22—C7	63.4 (9)
O5—C32—C31—C36	−179.2 (5)	C20—C21—C22—C23	−108.2 (7)
C33—C32—C31—C36	−0.3 (9)	C6—C21—C22—C23	130.2 (6)
O5—C32—C31—I1	0.7 (8)	C20—C21—C22—C7	128.0 (6)
C33—C32—C31—I1	179.5 (4)	C6—C21—C22—C7	6.5 (5)
C1—N1—C3—C4	2.1 (9)	C5—C6—C7—C8	126.0 (6)
C5—C4—C3—N1	2.0 (9)	C21—C6—C7—C8	−115.7 (6)
C3—C4—C5—C2	−4.5 (9)	C5—C6—C7—C22	−111.9 (6)
C3—C4—C5—C6	168.9 (6)	C21—C6—C7—C22	6.4 (5)
C36—C35—C34—O6	179.9 (5)	C23—C22—C7—C8	−8.7 (9)
I2—C35—C34—O6	−4.8 (7)	C21—C22—C7—C8	114.6 (6)
C36—C35—C34—C33	0.8 (8)	C23—C22—C7—C6	−129.9 (6)
I2—C35—C34—C33	176.2 (4)	C21—C22—C7—C6	−6.6 (5)
O6—C34—C33—C32	179.5 (5)	C6—C7—C8—C11	−173.4 (7)
C35—C34—C33—C32	−1.4 (9)	C22—C7—C8—C11	80.5 (9)
O5—C32—C33—C34	180.0 (6)	C6—C7—C8—C9	7.8 (10)
C31—C32—C33—C34	1.2 (9)	C22—C7—C8—C9	−98.3 (9)
C16—N2—C18—C19	−3.0 (9)	C24—C23—C26—C27	−0.3 (12)
C3—N1—C1—C2	−3.7 (9)	C22—C23—C26—C27	176.6 (8)
C19—C20—C17—C16	−3.9 (9)	C23—C24—C25—C28	−1.6 (13)
C21—C20—C17—C16	169.7 (6)	C11—C8—C9—C10	0.7 (13)
C17—C20—C19—C18	3.6 (9)	C7—C8—C9—C10	179.6 (8)
C21—C20—C19—C18	−169.3 (6)	C9—C8—C11—C12	−0.7 (14)
N2—C18—C19—C20	−0.1 (10)	C7—C8—C11—C12	−179.6 (9)
N1—C1—C2—C5	1.1 (10)	C24—C25—C28—C27	−0.2 (15)
C4—C5—C2—C1	3.1 (9)	C24—C25—C28—O4	174.9 (9)
C6—C5—C2—C1	−170.5 (6)	C25—C28—C27—C26	1.8 (17)
C18—N2—C16—C17	2.7 (9)	O4—C28—C27—C26	−173.4 (9)
C20—C17—C16—N2	0.8 (10)	C23—C26—C27—C28	−1.5 (15)
C2—C5—C6—C7	−145.5 (6)	C8—C9—C10—C13	2.0 (13)
C4—C5—C6—C7	41.4 (9)	C9—C10—C13—C12	−4.8 (14)
C2—C5—C6—C21	111.8 (7)	C9—C10—C13—O2	172.7 (8)
C4—C5—C6—C21	−61.3 (8)	C14—O2—C13—C10	70.2 (14)
C17—C20—C21—C22	−167.5 (6)	C14—O2—C13—C12	−112.2 (12)
C19—C20—C21—C22	5.4 (9)	C13—O2—C14—O1	8.5 (17)
C17—C20—C21—C6	−59.5 (7)	C13—O2—C14—C15	−175.6 (10)
C19—C20—C21—C6	113.5 (7)	C8—C11—C12—C13	−2.1 (16)
C5—C6—C21—C20	−11.6 (8)	C10—C13—C12—C11	4.9 (15)
C7—C6—C21—C20	−130.9 (6)	O2—C13—C12—C11	−172.7 (9)
C5—C6—C21—C22	112.6 (6)	O3—C29—O4—C28	5.5 (19)
C7—C6—C21—C22	−6.7 (5)	C30—C29—O4—C28	−177.6 (11)
C26—C23—C24—C25	1.8 (11)	C27—C28—O4—C29	−122.7 (13)
C22—C23—C24—C25	−175.0 (7)	C25—C28—O4—C29	62.0 (15)

(mcg16113)

Crystal data

C26H22N2O2	F(000) = 3328
Mr = 394.45	Dx = 1.217 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 19.7244 (19) Å	Cell parameters from 9907 reflections
b = 12.3920 (12) Å	θ = 2.3–24.0°
c = 35.750 (3) Å	µ = 0.08 mm^−1
β = 99.796 (6)°	T = 190 K
V = 8610.8 (14) Å^3	Prism, colorless
Z = 16	0.42 × 0.23 × 0.14 mm

Data collection

Nonius Kappa CCD diffractometer	5946 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.045
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0790 before and 0.0685 after correction. The Ratio of minimum to maximum transmission is 0.9038. The λ/2 correction factor is 0.00150.	θmax = 25.3°, θmin = 2.2°
Tmin = 0.979, Tmax = 0.989	h = −47→47
66161 measured reflections	k = −11→15
7778 independent reflections	l = −24→24

Refinement

Refinement on F^2	29 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 16.8778P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
7778 reflections	Δρmax = 0.63 e Å^−3
569 parameters	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.72942 (9)	0.53307 (16)	−0.71568 (5)	0.0400 (5)
O2	−0.43548 (10)	0.59912 (19)	−0.80622 (5)	0.0481 (6)
N1	−0.35329 (11)	0.34720 (19)	−0.49259 (6)	0.0383 (5)
N2	−0.17578 (10)	0.63768 (18)	−0.56540 (6)	0.0348 (5)
C1	−0.39147 (15)	0.4349 (2)	−0.49333 (8)	0.0424 (7)
H1A	−0.4004	0.4610	−0.4703	0.051*
C2	−0.41898 (14)	0.4904 (2)	−0.52556 (7)	0.0369 (6)
H2A	−0.4456	0.5516	−0.5239	0.044*
C3	−0.34021 (13)	0.3123 (2)	−0.52606 (7)	0.0383 (6)
H3	−0.3130	0.2512	−0.5265	0.046*
C4	−0.36562 (13)	0.3635 (2)	−0.56028 (7)	0.0355 (6)
H4	−0.3551	0.3368	−0.5829	0.043*
C5	−0.40686 (12)	0.4549 (2)	−0.56039 (7)	0.0287 (5)
C6	−0.43723 (12)	0.51578 (19)	−0.59586 (6)	0.0267 (5)
H6	−0.4727	0.5664	−0.5907	0.032*
C7	−0.46383 (11)	0.44646 (19)	−0.63197 (6)	0.0260 (5)
H7	−0.4600	0.3692	−0.6261	0.031*
C8	−0.53462 (11)	0.47376 (19)	−0.65322 (6)	0.0261 (5)
C9	−0.56052 (12)	0.5789 (2)	−0.65660 (7)	0.0314 (6)
H9	−0.5342	0.6350	−0.6445	0.038*
C10	−0.62498 (12)	0.6012 (2)	−0.67771 (7)	0.0302 (5)
H10	−0.6410	0.6719	−0.6799	0.036*
C11	−0.57567 (12)	0.39275 (19)	−0.67173 (7)	0.0290 (5)
H11	−0.5594	0.3222	−0.6702	0.035*
C12	−0.63989 (12)	0.4137 (2)	−0.69228 (7)	0.0308 (5)
H12	−0.6664	0.3574	−0.7041	0.037*
C13	−0.66525 (12)	0.5184 (2)	−0.69538 (7)	0.0281 (5)
C14	−0.23016 (13)	0.6667 (2)	−0.54998 (7)	0.0345 (6)
H14	−0.2220	0.7039	−0.5271	0.041*
C15	−0.29734 (13)	0.6452 (2)	−0.56563 (7)	0.0336 (6)
H15	−0.3328	0.6664	−0.5531	0.040*
C16	−0.19035 (13)	0.5851 (2)	−0.59847 (8)	0.0409 (7)
H16	−0.1540	0.5626	−0.6101	0.049*
C17	−0.25703 (13)	0.5623 (2)	−0.61640 (7)	0.0372 (6)
H17	−0.2644	0.5267	−0.6396	0.045*
C18	−0.31209 (12)	0.59260 (19)	−0.59974 (7)	0.0283 (5)
C19	−0.38546 (12)	0.57271 (19)	−0.61851 (6)	0.0270 (5)
H19	−0.4056	0.6413	−0.6285	0.032*
C20	−0.40065 (12)	0.48674 (19)	−0.64985 (7)	0.0273 (5)
H20	−0.3645	0.4317	−0.6456	0.033*
C22A	−0.38903 (15)	0.6171 (2)	−0.70247 (8)	0.0349 (4)	0.9
H22A	−0.3680	0.6656	−0.6842	0.042*	0.9
C23A	−0.39682 (15)	0.6450 (2)	−0.74079 (8)	0.0381 (7)	0.9
H23A	−0.3816	0.7118	−0.7478	0.046*	0.9
C24A	−0.44114 (14)	0.4481 (2)	−0.71870 (8)	0.0330 (6)	0.9
H24A	−0.4560	0.3813	−0.7114	0.040*	0.9
C25A	−0.44889 (14)	0.4743 (2)	−0.75691 (8)	0.0340 (6)	0.9
H25A	−0.4688	0.4252	−0.7752	0.041*	0.9
O3	−0.33379 (9)	0.25911 (17)	−0.92208 (6)	0.0429 (5)
O4	−0.43287 (10)	0.76181 (16)	−0.97855 (5)	0.0397 (5)
N3	−0.80987 (11)	0.36427 (19)	−0.82231 (6)	0.0388 (5)
N4	−0.71359 (11)	0.77347 (17)	−0.80174 (6)	0.0354 (5)
C27	−0.79803 (13)	0.3622 (2)	−0.85783 (8)	0.0402 (7)
H27	−0.8352	0.3518	−0.8773	0.048*
C28	−0.73352 (12)	0.3747 (2)	−0.86751 (7)	0.0324 (6)
H28	−0.7282	0.3731	−0.8929	0.039*
C29	−0.75539 (14)	0.3796 (2)	−0.79518 (7)	0.0403 (7)
H29	−0.7624	0.3826	−0.7701	0.048*
C30	−0.68949 (13)	0.3911 (2)	−0.80225 (7)	0.0341 (6)
H30	−0.6532	0.4000	−0.7822	0.041*
C31	−0.67683 (11)	0.38962 (17)	−0.83929 (7)	0.0241 (5)
C32	−0.60522 (11)	0.41327 (18)	−0.84651 (6)	0.0225 (5)
H32	−0.5698	0.3791	−0.8277	0.027*
C33	−0.59106 (11)	0.39800 (18)	−0.88781 (6)	0.0231 (5)
H33	−0.6287	0.3582	−0.9033	0.028*
C34	−0.52234 (11)	0.35524 (17)	−0.89380 (6)	0.0227 (5)
C35	−0.51959 (12)	0.29388 (18)	−0.92598 (6)	0.0255 (5)
H35	−0.5605	0.2752	−0.9416	0.031*
C36	−0.45791 (12)	0.25952 (19)	−0.93561 (6)	0.0269 (5)
H36	−0.4580	0.2171	−0.9571	0.032*
C37	−0.45947 (12)	0.38217 (19)	−0.87127 (7)	0.0288 (5)
H37	−0.4594	0.4227	−0.8494	0.035*
C38	−0.39732 (12)	0.3500 (2)	−0.88081 (7)	0.0308 (5)
H38	−0.3562	0.3696	−0.8655	0.037*
C39	−0.39631 (12)	0.2884 (2)	−0.91323 (7)	0.0283 (5)
C40	−0.72482 (12)	0.7520 (2)	−0.83892 (7)	0.0323 (6)
H40	−0.7594	0.7899	−0.8544	0.039*
C41	−0.68798 (12)	0.67688 (19)	−0.85561 (7)	0.0295 (5)
H41	−0.6986	0.6645	−0.8816	0.035*
C42	−0.66249 (14)	0.7180 (2)	−0.78056 (7)	0.0392 (6)
H42	−0.6535	0.7311	−0.7546	0.047*
C43	−0.62270 (13)	0.6428 (2)	−0.79515 (7)	0.0351 (6)
H43	−0.5875	0.6075	−0.7792	0.042*
C44	−0.63512 (11)	0.61970 (17)	−0.83381 (6)	0.0231 (5)
C45	−0.59211 (11)	0.53848 (17)	−0.85054 (6)	0.0214 (5)
H45	−0.5435	0.5533	−0.8408	0.026*
C46	−0.60078 (11)	0.52348 (17)	−0.89380 (6)	0.0220 (5)
H46	−0.6488	0.5380	−0.9050	0.026*
C47	−0.55471 (11)	0.58606 (18)	−0.91538 (6)	0.0225 (5)
C48	−0.55605 (13)	0.5668 (2)	−0.95385 (7)	0.0303 (5)
H48	−0.5853	0.5140	−0.9660	0.036*
C49	−0.51495 (13)	0.6243 (2)	−0.97442 (7)	0.0332 (6)
H49	−0.5162	0.6089	−1.0000	0.040*
C50	−0.51002 (11)	0.66463 (18)	−0.89836 (6)	0.0244 (5)
H50	−0.5072	0.6777	−0.8725	0.029*
C51	−0.46921 (11)	0.72459 (19)	−0.91885 (6)	0.0265 (5)
H51	−0.4402	0.7779	−0.9068	0.032*
C52	−0.47199 (12)	0.70463 (19)	−0.95712 (6)	0.0266 (5)
C24B	−0.3905 (6)	0.4492 (4)	−0.71690 (9)	0.0335 (8)	0.1
H24B	−0.3714	0.3831	−0.7085	0.040*	0.1
C25B	−0.3981 (6)	0.4760 (5)	−0.75514 (8)	0.0345 (9)	0.1
H25B	−0.3841	0.4278	−0.7723	0.041*	0.1
C26	−0.42664 (12)	0.5748 (2)	−0.76776 (5)	0.0340 (6)
C23B	−0.4475 (6)	0.6467 (5)	−0.74214 (9)	0.0381 (7)	0.1
H23B	−0.4666	0.7128	−0.7506	0.046*	0.1
C22B	−0.4398 (6)	0.6199 (5)	−0.70390 (8)	0.0349 (4)	0.1
H22B	−0.4538	0.6681	−0.6868	0.042*	0.1
C21	−0.41132 (11)	0.5211 (2)	−0.69128 (5)	0.0284 (5)
H1	−0.7469 (17)	0.601 (3)	−0.7143 (9)	0.066 (10)*
H2	−0.3961 (18)	0.621 (3)	−0.8118 (9)	0.059 (10)*
H3A	−0.3423 (17)	0.227 (3)	−0.9431 (10)	0.065 (11)*
H4A	−0.4017 (17)	0.803 (3)	−0.9633 (9)	0.058 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0287 (9)	0.0425 (11)	0.0431 (11)	0.0095 (8)	−0.0099 (8)	−0.0148 (9)
O2	0.0303 (10)	0.0935 (17)	0.0205 (9)	−0.0141 (10)	0.0041 (8)	0.0063 (10)
N1	0.0397 (12)	0.0473 (14)	0.0263 (11)	−0.0135 (11)	0.0013 (9)	0.0102 (10)
N2	0.0285 (11)	0.0496 (14)	0.0258 (11)	−0.0119 (10)	0.0038 (9)	0.0019 (10)
C1	0.0587 (18)	0.0427 (17)	0.0290 (14)	−0.0170 (14)	0.0162 (13)	−0.0009 (12)
C2	0.0443 (15)	0.0347 (14)	0.0335 (14)	−0.0063 (12)	0.0124 (12)	0.0017 (11)
C3	0.0315 (13)	0.0441 (16)	0.0394 (15)	−0.0008 (12)	0.0060 (11)	0.0095 (13)
C4	0.0366 (14)	0.0482 (16)	0.0230 (13)	−0.0067 (12)	0.0091 (11)	−0.0005 (11)
C5	0.0230 (12)	0.0329 (13)	0.0288 (13)	−0.0094 (10)	0.0001 (10)	0.0048 (10)
C6	0.0253 (12)	0.0297 (13)	0.0261 (12)	0.0003 (10)	0.0072 (10)	−0.0023 (10)
C7	0.0287 (12)	0.0244 (12)	0.0247 (12)	0.0004 (10)	0.0045 (10)	0.0017 (10)
C8	0.0231 (12)	0.0344 (13)	0.0222 (12)	0.0066 (10)	0.0076 (9)	0.0069 (10)
C9	0.0284 (13)	0.0342 (14)	0.0309 (13)	−0.0051 (11)	0.0029 (10)	−0.0034 (11)
C10	0.0280 (12)	0.0272 (13)	0.0335 (13)	0.0070 (10)	0.0000 (10)	−0.0044 (10)
C11	0.0345 (13)	0.0252 (12)	0.0280 (13)	0.0038 (10)	0.0071 (10)	0.0000 (10)
C12	0.0312 (13)	0.0308 (13)	0.0299 (13)	0.0018 (11)	0.0042 (10)	−0.0065 (11)
C13	0.0249 (12)	0.0348 (14)	0.0240 (12)	0.0061 (10)	0.0024 (9)	−0.0025 (10)
C14	0.0336 (14)	0.0473 (16)	0.0227 (12)	−0.0094 (12)	0.0050 (10)	−0.0019 (11)
C15	0.0296 (13)	0.0423 (15)	0.0292 (13)	−0.0042 (11)	0.0056 (10)	0.0021 (11)
C16	0.0325 (14)	0.0563 (18)	0.0371 (15)	−0.0090 (13)	0.0150 (12)	−0.0062 (13)
C17	0.0387 (15)	0.0441 (16)	0.0289 (14)	−0.0079 (12)	0.0064 (11)	−0.0073 (12)
C18	0.0299 (12)	0.0282 (13)	0.0267 (12)	−0.0042 (10)	0.0049 (10)	0.0068 (10)
C19	0.0288 (12)	0.0269 (12)	0.0253 (12)	0.0013 (10)	0.0044 (10)	0.0019 (10)
C20	0.0233 (12)	0.0294 (13)	0.0294 (13)	0.0002 (10)	0.0049 (10)	−0.0002 (10)
C22A	0.0389 (8)	0.0395 (9)	0.0260 (8)	−0.0094 (8)	0.0047 (7)	−0.0062 (7)
C23A	0.0426 (16)	0.0412 (16)	0.0309 (12)	−0.0157 (14)	0.0073 (11)	0.0002 (11)
C24A	0.0371 (15)	0.0359 (15)	0.0272 (12)	−0.0034 (13)	0.0088 (11)	−0.0048 (11)
C25A	0.0341 (14)	0.0433 (16)	0.0248 (12)	−0.0051 (13)	0.0055 (11)	−0.0074 (11)
O3	0.0283 (10)	0.0639 (13)	0.0366 (11)	0.0101 (9)	0.0056 (8)	−0.0197 (10)
O4	0.0406 (10)	0.0517 (12)	0.0280 (10)	−0.0219 (9)	0.0091 (8)	0.0008 (9)
N3	0.0324 (12)	0.0500 (14)	0.0375 (12)	−0.0129 (10)	0.0158 (10)	−0.0122 (11)
N4	0.0345 (12)	0.0347 (12)	0.0369 (12)	0.0081 (10)	0.0056 (9)	−0.0086 (10)
C27	0.0296 (13)	0.0565 (18)	0.0358 (15)	−0.0115 (12)	0.0096 (11)	−0.0143 (13)
C28	0.0304 (13)	0.0420 (15)	0.0269 (13)	−0.0043 (11)	0.0109 (10)	−0.0068 (11)
C29	0.0422 (15)	0.0531 (17)	0.0294 (14)	−0.0132 (13)	0.0170 (12)	−0.0066 (12)
C30	0.0340 (14)	0.0425 (15)	0.0262 (13)	−0.0087 (11)	0.0064 (11)	−0.0016 (11)
C31	0.0258 (12)	0.0162 (11)	0.0316 (13)	−0.0031 (9)	0.0088 (10)	−0.0012 (9)
C32	0.0244 (11)	0.0202 (11)	0.0236 (12)	0.0016 (9)	0.0058 (9)	0.0005 (9)
C33	0.0238 (11)	0.0221 (12)	0.0241 (12)	−0.0034 (9)	0.0061 (9)	−0.0017 (9)
C34	0.0253 (11)	0.0193 (11)	0.0249 (12)	−0.0006 (9)	0.0081 (9)	0.0013 (9)
C35	0.0272 (12)	0.0237 (12)	0.0257 (12)	−0.0025 (10)	0.0045 (10)	−0.0011 (10)
C36	0.0334 (13)	0.0284 (13)	0.0200 (11)	0.0044 (10)	0.0078 (10)	−0.0046 (10)
C37	0.0343 (13)	0.0289 (13)	0.0239 (12)	0.0040 (10)	0.0072 (10)	−0.0065 (10)
C38	0.0268 (12)	0.0374 (14)	0.0271 (13)	0.0022 (11)	0.0011 (10)	−0.0064 (11)
C39	0.0276 (12)	0.0325 (13)	0.0255 (12)	0.0063 (10)	0.0067 (10)	−0.0029 (10)
C40	0.0291 (13)	0.0302 (13)	0.0363 (14)	0.0070 (10)	0.0013 (11)	−0.0030 (11)
C41	0.0300 (13)	0.0301 (13)	0.0282 (13)	0.0013 (10)	0.0041 (10)	−0.0035 (10)
C42	0.0446 (15)	0.0425 (16)	0.0294 (14)	0.0114 (13)	0.0027 (12)	−0.0083 (12)
C43	0.0368 (14)	0.0366 (15)	0.0297 (13)	0.0119 (11)	−0.0010 (11)	−0.0036 (11)
C44	0.0214 (11)	0.0206 (11)	0.0276 (12)	−0.0018 (9)	0.0054 (9)	0.0002 (9)
C45	0.0195 (11)	0.0220 (11)	0.0228 (11)	−0.0009 (9)	0.0039 (9)	−0.0011 (9)
C46	0.0203 (11)	0.0218 (11)	0.0237 (12)	0.0003 (9)	0.0036 (9)	−0.0001 (9)
C47	0.0219 (11)	0.0210 (11)	0.0243 (12)	0.0030 (9)	0.0027 (9)	0.0022 (9)
C48	0.0364 (13)	0.0292 (13)	0.0239 (12)	−0.0103 (11)	0.0015 (10)	−0.0023 (10)
C49	0.0441 (15)	0.0370 (14)	0.0190 (12)	−0.0090 (12)	0.0065 (11)	−0.0030 (10)
C50	0.0279 (12)	0.0263 (12)	0.0195 (11)	−0.0002 (10)	0.0051 (9)	−0.0007 (9)
C51	0.0241 (12)	0.0283 (12)	0.0258 (12)	−0.0042 (10)	0.0008 (9)	−0.0012 (10)
C52	0.0263 (12)	0.0293 (13)	0.0245 (12)	−0.0018 (10)	0.0052 (9)	0.0050 (10)
C24B	0.0376 (18)	0.0368 (18)	0.0271 (14)	−0.0034 (16)	0.0081 (14)	−0.0056 (13)
C25B	0.0345 (18)	0.0437 (19)	0.0255 (14)	−0.0052 (17)	0.0058 (13)	−0.0066 (13)
C26	0.0204 (11)	0.0620 (18)	0.0208 (12)	−0.0074 (12)	0.0064 (9)	−0.0006 (12)
C23B	0.0426 (16)	0.0412 (16)	0.0309 (12)	−0.0157 (14)	0.0073 (11)	0.0002 (11)
C22B	0.0389 (8)	0.0395 (9)	0.0260 (8)	−0.0094 (8)	0.0047 (7)	−0.0062 (7)
C21	0.0213 (11)	0.0417 (14)	0.0230 (12)	0.0021 (10)	0.0061 (9)	0.0014 (11)

Geometric parameters (Å, º)

O1—C13	1.360 (3)	N3—C29	1.333 (3)
O1—H1	0.92 (4)	N4—C40	1.336 (3)
O2—C26	1.389 (2)	N4—C42	1.342 (3)
O2—H2	0.88 (3)	C27—H27	0.9300
N1—C1	1.320 (4)	C27—C28	1.383 (3)
N1—C3	1.338 (3)	C28—H28	0.9300
N2—C14	1.336 (3)	C28—C31	1.385 (3)
N2—C16	1.338 (3)	C29—H29	0.9300
C1—H1A	0.9300	C29—C30	1.373 (3)
C1—C2	1.372 (4)	C30—H30	0.9300
C2—H2A	0.9300	C30—C31	1.389 (3)
C2—C5	1.379 (4)	C31—C32	1.507 (3)
C3—H3	0.9300	C32—H32	0.9800
C3—C4	1.393 (4)	C32—C33	1.560 (3)
C4—H4	0.9300	C32—C45	1.584 (3)
C4—C5	1.394 (4)	C33—H33	0.9800
C5—C6	1.509 (3)	C33—C34	1.504 (3)
C6—H6	0.9800	C33—C46	1.577 (3)
C6—C7	1.565 (3)	C34—C35	1.388 (3)
C6—C19	1.574 (3)	C34—C37	1.399 (3)
C7—H7	0.9800	C35—H35	0.9300
C7—C8	1.510 (3)	C35—C36	1.387 (3)
C7—C20	1.575 (3)	C36—H36	0.9300
C8—C9	1.397 (3)	C36—C39	1.383 (3)
C8—C11	1.385 (3)	C37—H37	0.9300
C9—H9	0.9300	C37—C38	1.386 (3)
C9—C10	1.391 (3)	C38—H38	0.9300
C10—H10	0.9300	C38—C39	1.391 (3)
C10—C13	1.382 (3)	C40—H40	0.9300
C11—H11	0.9300	C40—C41	1.378 (3)
C11—C12	1.376 (3)	C41—H41	0.9300
C12—H12	0.9300	C41—C44	1.386 (3)
C12—C13	1.388 (3)	C42—H42	0.9300
C14—H14	0.9300	C42—C43	1.377 (3)
C14—C15	1.374 (3)	C43—H43	0.9300
C15—H15	0.9300	C43—C44	1.392 (3)
C15—C18	1.370 (3)	C44—C45	1.504 (3)
C16—H16	0.9300	C45—H45	0.9800
C16—C17	1.390 (4)	C45—C46	1.538 (3)
C17—H17	0.9300	C46—H46	0.9800
C17—C18	1.377 (3)	C46—C47	1.504 (3)
C18—C19	1.508 (3)	C47—C48	1.392 (3)
C19—H19	0.9800	C47—C50	1.383 (3)
C19—C20	1.538 (3)	C48—H48	0.9300
C20—H20	0.9800	C48—C49	1.381 (3)
C20—C21	1.521 (3)	C49—H49	0.9300
C22A—H22A	0.9300	C49—C52	1.383 (3)
C22A—C23A	1.396 (4)	C50—H50	0.9300
C22A—C21	1.352 (4)	C50—C51	1.392 (3)
C23—H23	0.9300	C51—H51	0.9300
C23—C26	1.357 (4)	C51—C52	1.382 (3)
C24—H24	0.9300	C24B—H24B	0.9300
C24—C25	1.387 (4)	C24B—C25B	1.3900
C24—C21	1.389 (4)	C24B—C21	1.3900
C25—H25	0.9300	C25B—H25B	0.9300
C25—C26	1.397 (4)	C25B—C26	1.3900
O3—C39	1.373 (3)	C26—C23B	1.3900
O3—H3A	0.84 (4)	C23B—H23B	0.9300
O4—C52	1.373 (3)	C23B—C22B	1.3900
O4—H4A	0.91 (3)	C22B—H22B	0.9300
N3—C27	1.330 (3)	C22B—C21	1.3900
C13—O1—H1	115 (2)	C31—C30—H30	119.9
C26—O2—H2	109 (2)	C28—C31—C30	116.3 (2)
C1—N1—C3	116.4 (2)	C28—C31—C32	124.4 (2)
C14—N2—C16	115.4 (2)	C30—C31—C32	119.1 (2)
N1—C1—H1A	117.5	C31—C32—H32	112.2
N1—C1—C2	124.9 (3)	C31—C32—C33	117.54 (18)
C2—C1—H1A	117.5	C31—C32—C45	112.23 (17)
C1—C2—H2A	120.2	C33—C32—H32	112.2
C1—C2—C5	119.6 (3)	C33—C32—C45	88.54 (16)
C5—C2—H2A	120.2	C45—C32—H32	112.2
N1—C3—H3	118.6	C32—C33—H33	110.9
N1—C3—C4	122.9 (3)	C32—C33—C46	88.38 (16)
C4—C3—H3	118.6	C34—C33—C32	119.23 (19)
C3—C4—H4	120.2	C34—C33—H33	110.9
C3—C4—C5	119.7 (2)	C34—C33—C46	114.82 (18)
C5—C4—H4	120.2	C46—C33—H33	110.9
C2—C5—C4	116.6 (2)	C35—C34—C33	118.3 (2)
C2—C5—C6	119.6 (2)	C35—C34—C37	116.9 (2)
C4—C5—C6	123.8 (2)	C37—C34—C33	124.4 (2)
C5—C6—H6	110.9	C34—C35—H35	118.9
C5—C6—C7	116.6 (2)	C36—C35—C34	122.3 (2)
C5—C6—C19	117.18 (19)	C36—C35—H35	118.9
C7—C6—H6	110.9	C35—C36—H36	120.1
C7—C6—C19	88.72 (17)	C39—C36—C35	119.9 (2)
C19—C6—H6	110.9	C39—C36—H36	120.1
C6—C7—H7	111.0	C34—C37—H37	119.2
C6—C7—C20	89.05 (17)	C38—C37—C34	121.6 (2)
C8—C7—C6	116.33 (19)	C38—C37—H37	119.2
C8—C7—H7	111.0	C37—C38—H38	119.9
C8—C7—C20	116.89 (19)	C37—C38—C39	120.1 (2)
C20—C7—H7	111.0	C39—C38—H38	119.9
C9—C8—C7	123.1 (2)	O3—C39—C36	122.2 (2)
C11—C8—C7	119.6 (2)	O3—C39—C38	118.5 (2)
C11—C8—C9	117.3 (2)	C36—C39—C38	119.2 (2)
C8—C9—H9	119.4	N4—C40—H40	118.2
C10—C9—C8	121.3 (2)	N4—C40—C41	123.7 (2)
C10—C9—H9	119.4	C41—C40—H40	118.2
C9—C10—H10	120.0	C40—C41—H41	119.9
C13—C10—C9	120.1 (2)	C40—C41—C44	120.3 (2)
C13—C10—H10	120.0	C44—C41—H41	119.9
C8—C11—H11	119.0	N4—C42—H42	118.2
C12—C11—C8	121.9 (2)	N4—C42—C43	123.7 (2)
C12—C11—H11	119.0	C43—C42—H42	118.2
C11—C12—H12	119.8	C42—C43—H43	120.0
C11—C12—C13	120.3 (2)	C42—C43—C44	120.0 (2)
C13—C12—H12	119.8	C44—C43—H43	120.0
O1—C13—C10	123.7 (2)	C41—C44—C43	116.2 (2)
O1—C13—C12	117.2 (2)	C41—C44—C45	122.7 (2)
C10—C13—C12	119.1 (2)	C43—C44—C45	121.1 (2)
N2—C14—H14	117.7	C32—C45—H45	108.4
N2—C14—C15	124.5 (2)	C44—C45—C32	120.50 (18)
C15—C14—H14	117.7	C44—C45—H45	108.4
C14—C15—H15	120.0	C44—C45—C46	120.46 (18)
C18—C15—C14	119.9 (2)	C46—C45—C32	88.91 (16)
C18—C15—H15	120.0	C46—C45—H45	108.4
N2—C16—H16	118.3	C33—C46—H46	108.8
N2—C16—C17	123.4 (2)	C45—C46—C33	89.57 (16)
C17—C16—H16	118.3	C45—C46—H46	108.8
C16—C17—H17	120.0	C47—C46—C33	120.55 (18)
C18—C17—C16	120.0 (2)	C47—C46—C45	118.69 (18)
C18—C17—H17	120.0	C47—C46—H46	108.8
C15—C18—C17	116.8 (2)	C48—C47—C46	120.5 (2)
C15—C18—C19	121.1 (2)	C50—C47—C46	122.2 (2)
C17—C18—C19	122.1 (2)	C50—C47—C48	117.3 (2)
C6—C19—H19	108.6	C47—C48—H48	119.2
C18—C19—C6	120.12 (19)	C49—C48—C47	121.6 (2)
C18—C19—H19	108.6	C49—C48—H48	119.2
C18—C19—C20	119.4 (2)	C48—C49—H49	119.9
C20—C19—C6	90.06 (17)	C48—C49—C52	120.2 (2)
C20—C19—H19	108.6	C52—C49—H49	119.9
C7—C20—H20	108.8	C47—C50—H50	119.1
C19—C20—C7	89.63 (17)	C47—C50—C51	121.8 (2)
C19—C20—H20	108.8	C51—C50—H50	119.1
C21—C20—C7	119.74 (19)	C50—C51—H51	120.1
C21—C20—C19	119.5 (2)	C52—C51—C50	119.8 (2)
C21—C20—H20	108.8	C52—C51—H51	120.1
C23—C22A—H22A	119.3	O4—C52—C49	118.8 (2)
C21—C22A—H22A	119.3	O4—C52—C51	121.9 (2)
C21—C22A—C23A	121.4 (3)	C51—C52—C49	119.3 (2)
C22A—C23A—H23A	120.0	C25B—C24B—H24B	120.0
C26—C23A—C22A	120.0 (3)	C25B—C24B—C21	120.0
C26—C23—H23	120.0	C21—C24B—H24B	120.0
C25—C24—H24	119.8	C24B—C25B—H25B	120.0
C25—C24—C21	120.3 (3)	C26—C25B—C24B	120.0
C21—C24—H24	119.8	C26—C25B—H25B	120.0
C24—C25—H25	120.2	O2—C26—C25A	118.4 (2)
C24—C25—C26	119.7 (2)	O2—C26—C25B	119.2 (2)
C26—C25—H25	120.2	O2—C26—C23B	120.8 (2)
C39—O3—H3A	106 (2)	C23A—C26—O2	122.0 (2)
C52—O4—H4A	110 (2)	C23A—C26—C25A	119.6 (2)
C27—N3—C29	116.5 (2)	C23B—C26—C25B	120.0
C40—N4—C42	116.1 (2)	C26—C23B—H23B	120.0
N3—C27—H27	118.1	C26—C23B—C22B	120.0
N3—C27—C28	123.7 (2)	C22B—C23B—H23B	120.0
C28—C27—H27	118.1	C23B—C22B—H22B	120.0
C27—C28—H28	120.1	C21—C22B—C23B	120.0
C27—C28—C31	119.7 (2)	C21—C22B—H22B	120.0
C31—C28—H28	120.1	C22A—C21—C24A	119.0 (2)
N3—C29—H29	118.2	C24A—C21—C20	118.5 (2)
N3—C29—C30	123.5 (2)	C24B—C21—C20	117.04 (18)
C30—C29—H29	118.2	C22B—C21—C20	122.96 (18)
C29—C30—H30	119.9	C22B—C21—C24B	120.0
C29—C30—C31	120.2 (2)
O2—C26—C23B—C22B	178.4 (2)	C27—N3—C29—C30	−1.1 (4)
N1—C1—C2—C5	−0.3 (4)	C27—C28—C31—C30	−0.1 (4)
N1—C3—C4—C5	−0.3 (4)	C27—C28—C31—C32	−174.7 (2)
N2—C14—C15—C18	−1.4 (4)	C28—C31—C32—C33	−12.4 (3)
N2—C16—C17—C18	−1.2 (4)	C28—C31—C32—C45	88.1 (3)
C1—N1—C3—C4	−0.8 (4)	C29—N3—C27—C28	0.1 (4)
C1—C2—C5—C4	−0.9 (4)	C29—C30—C31—C28	−0.8 (4)
C1—C2—C5—C6	179.9 (2)	C29—C30—C31—C32	174.1 (2)
C2—C5—C6—C7	−142.1 (2)	C30—C31—C32—C33	173.2 (2)
C2—C5—C6—C19	114.7 (2)	C30—C31—C32—C45	−86.3 (3)
C3—N1—C1—C2	1.1 (4)	C31—C32—C33—C34	−143.7 (2)
C3—C4—C5—C2	1.2 (3)	C31—C32—C33—C46	98.6 (2)
C3—C4—C5—C6	−179.6 (2)	C31—C32—C45—C44	22.2 (3)
C4—C5—C6—C7	38.7 (3)	C31—C32—C45—C46	−103.03 (19)
C4—C5—C6—C19	−64.5 (3)	C32—C33—C34—C35	148.9 (2)
C5—C6—C7—C8	132.1 (2)	C32—C33—C34—C37	−38.1 (3)
C5—C6—C7—C20	−108.2 (2)	C32—C33—C46—C45	16.32 (16)
C5—C6—C19—C18	−17.2 (3)	C32—C33—C46—C47	139.9 (2)
C5—C6—C19—C20	107.4 (2)	C32—C45—C46—C33	−16.07 (15)
C6—C7—C8—C9	34.9 (3)	C32—C45—C46—C47	−141.19 (19)
C6—C7—C8—C11	−147.8 (2)	C33—C32—C45—C44	141.5 (2)
C6—C7—C20—C19	−12.11 (17)	C33—C32—C45—C46	16.25 (16)
C6—C7—C20—C21	−136.4 (2)	C33—C34—C35—C36	174.0 (2)
C6—C19—C20—C7	12.04 (17)	C33—C34—C37—C38	−172.5 (2)
C6—C19—C20—C21	136.5 (2)	C33—C46—C47—C48	65.2 (3)
C7—C6—C19—C18	−136.7 (2)	C33—C46—C47—C50	−115.2 (2)
C7—C6—C19—C20	−12.12 (17)	C34—C33—C46—C45	−105.4 (2)
C7—C8—C9—C10	177.4 (2)	C34—C33—C46—C47	18.2 (3)
C7—C8—C11—C12	−178.4 (2)	C34—C35—C36—C39	−1.4 (4)
C7—C20—C21—C22A	128.1 (3)	C34—C37—C38—C39	−0.7 (4)
C7—C20—C21—C24A	−56.1 (3)	C35—C34—C37—C38	0.6 (3)
C7—C20—C21—C24B	−103.6 (6)	C35—C36—C39—O3	−178.1 (2)
C7—C20—C21—C22B	77.0 (7)	C35—C36—C39—C38	1.3 (4)
C8—C7—C20—C19	107.2 (2)	C37—C34—C35—C36	0.5 (3)
C8—C7—C20—C21	−17.2 (3)	C37—C38—C39—O3	179.2 (2)
C8—C9—C10—C13	1.0 (4)	C37—C38—C39—C36	−0.3 (4)
C8—C11—C12—C13	0.7 (4)	C40—N4—C42—C43	0.1 (4)
C9—C8—C11—C12	−0.9 (3)	C40—C41—C44—C43	0.2 (3)
C9—C10—C13—O1	178.3 (2)	C40—C41—C44—C45	−178.6 (2)
C9—C10—C13—C12	−1.2 (4)	C41—C44—C45—C32	−102.7 (3)
C11—C8—C9—C10	0.0 (3)	C41—C44—C45—C46	6.0 (3)
C11—C12—C13—O1	−179.2 (2)	C42—N4—C40—C41	0.9 (4)
C11—C12—C13—C10	0.3 (4)	C42—C43—C44—C41	0.7 (4)
C14—N2—C16—C17	0.8 (4)	C42—C43—C44—C45	179.6 (2)
C14—C15—C18—C17	0.9 (4)	C43—C44—C45—C32	78.5 (3)
C14—C15—C18—C19	−177.0 (2)	C43—C44—C45—C46	−172.8 (2)
C15—C18—C19—C6	−53.0 (3)	C44—C45—C46—C33	−141.4 (2)
C15—C18—C19—C20	−162.2 (2)	C44—C45—C46—C47	93.5 (2)
C16—N2—C14—C15	0.5 (4)	C45—C32—C33—C34	101.9 (2)
C16—C17—C18—C15	0.3 (4)	C45—C32—C33—C46	−15.85 (15)
C16—C17—C18—C19	178.2 (2)	C45—C46—C47—C48	173.5 (2)
C17—C18—C19—C6	129.1 (3)	C45—C46—C47—C50	−6.9 (3)
C17—C18—C19—C20	20.0 (3)	C46—C33—C34—C35	−108.2 (2)
C18—C19—C20—C7	137.2 (2)	C46—C33—C34—C37	64.8 (3)
C18—C19—C20—C21	−98.3 (3)	C46—C47—C48—C49	179.1 (2)
C19—C6—C7—C8	−107.9 (2)	C46—C47—C50—C51	−177.9 (2)
C19—C6—C7—C20	11.84 (17)	C47—C48—C49—C52	−1.3 (4)
C19—C20—C21—C22A	19.8 (3)	C47—C50—C51—C52	−1.2 (3)
C19—C20—C21—C24A	−164.5 (2)	C48—C47—C50—C51	1.8 (3)
C19—C20—C21—C24B	148.0 (6)	C48—C49—C52—O4	−178.6 (2)
C19—C20—C21—C22B	−31.3 (7)	C48—C49—C52—C51	1.9 (4)
C20—C7—C8—C9	−68.5 (3)	C50—C47—C48—C49	−0.6 (4)
C20—C7—C8—C11	108.9 (2)	C50—C51—C52—O4	179.8 (2)
C22A—C23A—C26—O2	180.0 (3)	C50—C51—C52—C49	−0.7 (3)
C22A—C23A—C26—C25	−0.5 (4)	C24B—C25B—C26—O2	−178.4 (2)
C23A—C22A—C21—C20	177.3 (2)	C24B—C25B—C26—C23B	0.0
C23A—C22A—C21—C24A	1.5 (4)	C25B—C24B—C21—C20	−179.38 (19)
C24—C25—C26—O2	−179.6 (2)	C25B—C24B—C21—C22B	0.0
C24A—C25—C26—C23A	0.9 (4)	C25B—C26—C23B—C22B	0.0
C25—C24A—C21—C20	−177.0 (2)	C26—C23B—C22B—C21	0.0
C25—C24A—C21—C22A	−1.1 (4)	C23B—C22B—C21—C20	179.3 (2)
N3—C27—C28—C31	0.5 (4)	C23B—C22B—C21—C24B	0.0
N3—C29—C30—C31	1.5 (4)	C21—C22A—C23A—C26	−0.7 (4)
N4—C40—C41—C44	−1.1 (4)	C21—C24A—C25A—C26	−0.1 (4)
N4—C42—C43—C44	−0.9 (4)	C21—C24B—C25B—C26	0.0