Structure determination of two metal-organic complexes from high-resolution synchrotron powder diffraction data

The crystal structures of [1,2-bis(2,6-diisopropylphenylimino)acenaphthene-N,N′]carbonylchlororhodium(I) (1) and [N,N′-ethylene-bis(3-methylsalicylideneiminato)-O,N,N′,O′](tetrahydrofurfuryl)-cobalt(II) (2) have been determined from high-resolution synchrotron X-ray powder diffraction data. Compound 1 is the first neutral Rh complex, in contrast with findings in the literature, containing a bidentate nitrogen ligand, and compound 2 is the first three-dimensional structure of a (five-coordinated) tetrahydrofurfuryl­cobalt(III) complex. Grid-search and Rietveld refinement have been used to determine and refine the structures, respectively. Crystals of 1 are orthorhombic, space group Pbca, Z = 8, with cell parameters a = 21.729 (2), b = 27.376 (3), c = 11.580 (1) Å. Crystals of 2 are monoclinic, space group P2₁/n, Z = 4, a = 16.6701 (6), b = 9.4170 (4), c = 13.7088 (7) Å and β = 96.520 (3)°. Chemical diagrams for the two compounds are given. Soft restraints were applied during Rietveld refinement; for 1 converging to R_p = 8.4%, R_w = 11.0%, GoF = 2.3, and for 2 converging to R_p = 8.5%, R_w = 11.4%, GoF = 7.6.

1. Introduction.

The structure determinations presented in this paper are part of a series of attempts to determine crystal structures from X-ray powder diffraction data (Helmholdt et al., 1998; Goubitz et al., 1999, 2001; van Langevelde et al., 1999; Dova et al., 2001). The determination of crystal structures from single-crystal data has become a standard routine during the last decades provided it is possible to grow suitable crystals. If only powder is available then structure determination is certainly by no means a standard procedure. In the last decade a number of research groups have attempted to tackle this problem and a couple of program packages exist nowadays [e.g. POWSIM (Jansen et al., 1992a,b, 1993), SIRPOW (Altomare et al., 1994, 1995)]. The main problem in structure determination is the number of reflections with reliable intensity that can be extracted from a powder diffractogram. Particularly for lower symmetries (up to orthorhombic) and larger structures, the overlap of reflections often prevents the extraction of reliable intensities, especially at higher θ values. Standard ab initio determination procedures are hampered because data sets obtained from powder data are far from complete. The grid-search technique (Chernyshev & Schenk, 1998) used here can overcome this problem for molecules with known conformation. Only the lower angle part of the diffractogram, where overlap of reflections is less severe, is needed to obtain a reliable estimate of the position and the orientation of the molecule within the asymmetric unit. Variation of proper torsion angles can result in a more reliable structural model that can be used as a starting point in a refinement procedure.

2. Chemical background.

Compound 1 is a Rh complex containing a bidentate nitrogen ligand. These complexes are of great interest because of their catalytic activity in several types of reaction such as hydroformylation (Saus et al., 1983; Garcia et al., 1985; Clauti et al., 1986; Bayón et al., 1991; Botteghi & Paganelli, 1993), hydrogenation (Mestroni et al., 1977; Pasternak et al., 1976; Pasternak & Pruchnik, 1976; Zassinovich et al., 1976, 1977, 1987) and hydrogen transfer (Gillard et al., 1975). These complexes are also known for their electrocatalytic capability in the reduction of carbon dioxide (Bollinger et al., 1988). Compound 1 was prepared by reacting [Rh(CO)₂(Cl)]₂ with 2,6-diisopropylbis-(phenylimino)acenaphtene in dichloromethane. Details of the synthesis will be published elsewhere (Mahabiersing et al., 2001).

Organocobalt(III)salen complexes like 2 can be used as model compounds for coenzyme B₁₂ (5′-deoxyadenosylcobalamin). Similar to the coenzyme, the Co—C bond of (alkyl)Co(salen) complexes can be cleaved homolytically by heat or light to create a cobalt(II) complex and an alkyl radical. Co—C bond homolysis is the first step in a number of B₁₂-dependent enzymatic 1,2-rearrangement reactions (Halpern, 1985). The thus generated 5′-deoxyadenosyl radical abstracts an H atom from the substrate, after which a 1,2-migration occurs.

Structural investigations of the coenzyme and models thereof have provided valuable information on the relative weakness of the organometallic bond at the coenzyme (Toscano & Marzilli, 1984). A notable feature in the crystal structure of the coenzyme is the large Co—C—C angle of 125°. Since the tetrahydrofurfuryl ligand structurally resembles the 5′-deoxyadenosyl group, comparison of structural information on tetrahydrofurfurylcobalt(III) complexes with that of the coenzyme may show interesting similarities or differences. Tetrahydrofurfurylbromide was prepared according to a published procedure (Smith, 1955). (Tetrahydrofurfuryl)Co(3-mesalen) was synthesized by using the procedure for (n-butyl)Co(salen) (van Arkel et al., 1993).

3. Experimental

X-ray powder diffraction photographs of these samples were taken using an Enraf–Nonius FR 552 Guinier Johansson camera (Enraf–Nonius, Delft, The Netherlands) equipped with a Johansson monochromator (Roberts & Parrish, 1962) using Cu Kα₁ radiation, λ = 1.54060 Å. The samples were prepared by pressing the powder into a thin layer onto Mylar foil. To improve particle statistics the sample holder was rotated in the specimen plane. For indexing of the patterns the accurate positions of as many lines as possible were collected by reading out the Guinier photographs with an optical instrument. Using a Johansson LS-18 microdensitometer the Guinier photographs were digitized from 4.0 to 84.2° 2θ in steps of 0.01° 2θ. Cell parameters and (possible) space groups were determined using the program ITO (Visser, 1969).

X-ray powder diffraction patterns of both compounds were measured at the high-resolution powder diffraction station BM16 (Fitch, 1996) at the European Synchrotron Radiation Facility (ESRF, Grenoble, France) with λ = 0.65296 Å for 1 and λ = 0.65052 Å for 2. The wavelength was calibrated by measuring 11 peaks from NIST Si standard 640b (lattice parameter certified as 5.43094 Å). These peaks were fitted with a pseudo-Voigt profile function to obtain peak positions, accounting for asymmetry using the Finger–Cox–Jephcoat correction, and then fitting the wavelength and instrumental zero point to these positions via least squares. For data collection a capillary with a diameter of 1.5 mm was filled with powder and rotated during exposure. Continuous scans were made from 0.0 to 25.0° 2θ for 1 and 0.0 to 30.0° 2θ for 2 with 0.5° 2θ min⁻¹ and a sampling time of 50 ms. After data collection the scans were binned at 0.005° 2θ.

All data collections were performed at room temperature.

4. Structure solution and refinement

To obtain reflection intensities a full-pattern decomposition (FPD) procedure using the program MRIA (Zlokazov & Chernyshev, 1992) was performed: the high-resolution synchrotron powder diffraction patterns were fitted employing a split-type pseudo-Voigt peak profile function (Toraya, 1986). Some details of the FPD procedure are listed in Table 2.

Initial models of both compounds were built from similar complexes searched for in the Cambridge Structural Database (CSD) (Allen & Kennard, 1993) and the necessary changes were made using the program package Cerius² (Molecular Simulations Inc., 1995). Compound 1 (Fig. 1) could be built from the CSD entry WETGIL (van Asselt et al., 1994); replacing Pd by Rh and the CH₃ group by CO yielded the desired model, which was used in the grid-search procedure. For 2 the CSD entry ESALCP (Haller & Enemark, 1978) was used and by using Cerius² the molecule was completed with the tetrahydrofurfuryl moiety. This model was optimized using some cycles of energy minimization.

Figure 1 Chemical diagram of 1.

To position the molecule in the asymmetric part of the unit cell, the initial models were used in the grid-search procedure (Chernyshev & Schenk, 1998) performed by the program MRIA, using 50 low-angle X_obs [X_obs and R(X) are defined in expressions (1) and (2) of Chernyshev & Schenk (1998)] values extracted from the patterns after the FPD procedure. The model was translated and rotated through the asymmetric unit. The initial grid increments were 0.6 Å for molecule translations along a, b and c, and 30° for the three rotations around φ, ψ and κ angles. The minima found in this way were examined in more detail by gradually lowering the incremental steps in translation to 0.1 Å and in rotation to 0.5°, resulting in R(X) values of 37.2 and 45.6%, respectively. For 2 the model was further refined by using a script that automatically varied two torsion angles τ1 and τ2 (Fig. 2) in steps of 5° each and that updated the input for the grid search. This resulted in a minimum R(X) value of 35.1%.

Figure 2 Chemical diagram of 2 (the torsion angles varied are indicated by arrows).

The bond-restrained Rietveld refinement (RR) was performed using the same program suite MRIA. For both patterns the split-type pseudo-Voigt peak profile function (Toraya, 1986) was used. The preferred orientation was refined using the symmetrized harmonics expansion method (Ahtee et al., 1989; Järvinen, 1993).

In order to retain chemically realistic models a bond-restrained RR as described by Baerlocher (1993) was applied to all interatomic distances up to 3.0 Å (with σ = 1% of the ideal distance). The weight c_w (Baerlocher, 1993, p. 188) that weighs the residual function of the restraints S_R versus the Rietveld residual S_Y was gradually reduced from 209.4 to 1.0 for 1 and from 46.5 to 0.2 for 2.

During the refinement the U_iso values of identical atom types were coupled. The relevant crystal data and the results of the refinements are presented in Tables 1 and 2, respectively; selected bond distances and angles are listed in Tables 3 and 4.¹ Plots of the observed and calculated X-ray diffraction patterns and difference plots after RR and PLUTON (Spek, 1990) plots of both compounds are depicted in Figs. 3–6.

Table 1
Crystallographic data for compounds 1 and 2

	1	2
Formula	C37H40N2OClRh	C23H27N2O3Co
Space Group	Pbca	P21/n
a (Å)	21.729 (2)	16.6701 (6)
b (Å)	27.376 (3)	9.4170 (4)
c (Å)	11.579 (1)	13.7088 (7)
β(°)		96.520 (3)
V(Å^3)	6888 (2)	2138.1 (2)
Z	8	4
Wavelength (Å)	0.65296	0.65051
Dx (g cm^−3)	1.29	1.35
F(000) (electrons)	2768	920

Table 2
Details of the bond-restrained Rietveld refinement

R_p = Σ|y_obs − y_calc|/Σy_obs. R_wp = Σw(y_obs − y_calc)/Σwy_obs. The second line for GoF, R_p and R_wp indicates the results of the FPD procedure.

	1	2
M20	25.1	14.0
2θ region (°)	2.5–25.0	0.01–30.00
Number of datapoints	4500	5999
Number of reflections	1102	1182
Number of restraints	377	276
Number of variables
Structural
Lattice	3	4
Positional	126	87
Thermal	5	4
Other
Texture	9	15
Profile	19	19
Background	12	12
Zero shift	1	1
GoF	2.5	7.6
	2.3	8.0
Rp (%)	8.4	8.5
	7.7	8.6
Rwp (%)	11.1	11.4
	10.3	11.8

Table 3
Selected distances (Å) and angles (°) for 1

Rh—Cl	2.25 (3)	Rh—N2	2.06 (3)
Rh—N1	2.06 (3)	Rh—C13	1.99 (4)
Cl—Rh—N1	174.0 (10)	N1—Rh1—N2	80.0 (10)
Cl—Rh—N2	94.3 (9)	N1—Rh1—C13	94.3 (11)
Cl—Rh—C13	91.5 (10)	N2—Rh1—C13	174.2 (12)

Table 4
Selected distances (Å) and angles (°) for 2

Co—O1	1.84 (4)	Co—N2	1.94 (6)
Co—O2	1.94 (5)	Co—C19	2.04 (6)
Co—N1	1.86 (7)
O1—Co—O2	88 (2)	O2—Co—N2	92 (3)
O1—Co—N1	96 (2)	O2—Co—C19	84 (3)
O1—Co—N2	178 (2)	N1—Co—N2	84 (3)
O1—Co—C19	90 (2)	N1—Co—C19	94 (3)
O2—Co—N1	175 (2)	N2—Co—C19	93 (2)

Figure 3 Bond-restrained RR of 1. The upper curve illustrates the observed data, the middle curve illustrates the calculated data, while the lower curve shows the difference between the observed and calculated data. Markers of all reflections are included at the bottom.

Figure 4 Bond-restrained RR of 2. The upper curve illustrates the observed data, the middle curve illustrates the calculated data, while the lower curve shows the difference between the observed and calculated data. Markers of all reflections are included at the bottom

Figure 5 PLUTON plot of 1 after bond-restrained RR.

Figure 6 PLUTON plot of 2 after bond-restrained RR.

5. Discussion

5.1. Structural features of 1

After the RR, inspection of the observed and calculated pattern revealed some residual intensity. The shoulder at 4.3° and the single peak at 4.7° and other peaks in the difference pattern are considerably broader than the peaks belonging to Bragg reflections, suggesting some impurity in the sample. This could also explain the rather high peak in the difference pattern at 3.4°, because that peak has the same shape as the peaks mentioned before (Fig. 7). The same applies to some other peaks in the low-angle region of the difference pattern. During the Guinier measurements these same peaks were present in the first photograph, but photographs taken from the same sample a couple of hours later no longer showed these peaks. This suggests the presence of a solvent that, under the vacuum conditions in the Guinier–Johansson camera, (slowly) evaporated. The capillary used for measuring the synchrotron data was filled and closed immediately, so evaporation of possible solvent could be prevented.

Figure 7 Lower-angle part of the diffraction pattern of 1 (see §5.1)

The bond distances and angles are similar to those found in comparable complexes in the literature. All aromatic rings are planar and the coordination of the Rh atom is a regular octahedron.

Meanwhile, from 1, a single-crystal structure has also been determined (Mahabiersing et al., 2001). In that structure a solvent molecule (acetone) is present and the crystals are tetragonal with space group I4₁/a. Matching identical atoms of both structures led to an r.m.s. of 0.44 Å, the largest differences occurring in the diisopropylphenyl moieties (not taking those into account in the match led to an r.m.s. value of 0.10 Å). This is further evidence that the methods described in this paper lead to correctly determined and refined stuctures.

5.2. Structural features of 2

Compound 2 could only be refined by employing a very small damping factor (0.005) to avoid destroying the geometry of the molecule during refinement. Examination of the sample and the powder pattern revealed that this powder was of poor quality (maybe due to the crystallinity and/or particle size) and hardly any significant diffraction signal was present at diffraction angles beyond 20° 2θ; this may have caused the difficulties encountered during refinement. It is also noticeable that the full width at half-maximum of 1 is considerably smaller (minimum 0.014) than that of 2 (minimum 0.038). Attempting to refine 2 without the heavy damping was not successful; the only atoms that could be refined were the Co atom and the five atoms directly bonded to it, and every attempt to decrease the bond restraints or to release the other atomic positions failed; this RR converged to R_P = 10.3%.

Compound 2 is comparable with other Co-(salen) complexes from the literature. The equatorial atoms which are directly connected to the Co atom show some tetrahedral distortion which, in combination with the N,N′-ethylene bridge, lead to a slight deviation from planarity of both aromatic rings. This tetrahedral distortion was also observed in cobaloximes by De Ridder et al. (1996, and references therein). The tetrahydrofurfuryl moiety is almost perpendicular to the rest of the molecule.

Supporting information

Computing details

For both compounds, cell refinement: UnitCell; data reduction: MRIA; program(s) used to solve structure: MRIA; program(s) used to refine structure: MRIA; molecular graphics: CHEMDRAW and PLATON.

Figures

(Compound_1) chloro-CO-(bis(2,6-di-isoprpopylpheylimino)acenaphtene-N,N')-rhodium

Crystal data

C37H40ClN2ORh	V = 6888 (2) Å^3
Mr = 667.07	Z = 8
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.65296 Å
Hall symbol: -p 2ac 2ab	µ = 0.6 mm^−1
a = 21.729 (2) Å	T = 293 K
b = 27.376 (3) Å	cylinder, ? × 0.7 mm mm
c = 11.579 (1) Å

Data collection

ESRF BM16 diffractometer	Data collection mode: transmission
Radiation source: synchrotron	Scan method: continuous
Specimen mounting: capillary	2θmin = 2.500°, 2θmax = 25.00°, 2θstep = 0.005°

Refinement

Rp = 8.4	175 parameters
Rwp = 11.1	38 restraints
Rexp = ?	Calculated and kept fixed
χ^2 = 6.250
4500 data points	Background function: polynomal
Profile function: split-type pseudo-Voigt	Preferred orientation correction: 'Ahtee and Jarvinen'

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

	x	y	z	Biso*/Beq
Rh1	0.5684 (6)	0.3673 (4)	0.5327 (10)	*
Cl1	0.4653 (12)	0.3676 (9)	0.5116 (18)	*
N1	0.6610 (10)	0.3707 (8)	0.5681 (19)	*
N2	0.5655 (10)	0.3838 (8)	0.705 (2)	*
C1	0.6703 (10)	0.3808 (9)	0.6734 (18)	*
C2	0.7244 (10)	0.3815 (11)	0.7402 (17)	*
C3	0.7880 (12)	0.3750 (10)	0.7166 (16)	*
C4	0.8308 (11)	0.373 (2)	0.817 (3)	*
C5	0.8095 (12)	0.380 (3)	0.928 (3)	*
C6	0.7467 (12)	0.398 (4)	0.946 (3)	*
C7	0.7179 (12)	0.400 (3)	1.056 (2)	*
C8	0.6529 (14)	0.400 (2)	1.067 (2)	*
C9	0.6151 (9)	0.3976 (9)	0.971 (2)	*
C10	0.6424 (9)	0.3921 (10)	0.862 (2)	*
C11	0.6204 (10)	0.3875 (9)	0.746 (2)	*
C12	0.7058 (9)	0.3892 (14)	0.854 (2)	*
C13	0.5804 (12)	0.3525 (11)	0.366 (3)	*
O13	0.5851 (13)	0.3448 (11)	0.278 (3)	*
C14	0.7077 (11)	0.3555 (6)	0.4867 (18)	*
C15	0.7234 (12)	0.3054 (8)	0.476 (2)	*
C16	0.7707 (13)	0.2902 (8)	0.400 (2)	*
C18	0.7842 (13)	0.3743 (8)	0.340 (2)	*
C19	0.7381 (12)	0.3904 (8)	0.417 (2)	*
C20	0.6896 (11)	0.2656 (8)	0.549 (2)	*
C21	0.7335 (12)	0.2405 (8)	0.630 (2)	*
C22	0.6568 (10)	0.2288 (8)	0.471 (2)	*
C23	0.7212 (12)	0.4459 (9)	0.425 (2)	*
C24	0.7764 (13)	0.4753 (8)	0.467 (2)	*
C25	0.6980 (11)	0.4648 (8)	0.311 (2)	*
C26	0.5108 (10)	0.3813 (6)	0.775 (2)	*
C27	0.4782 (12)	0.4246 (8)	0.802 (2)	*
C28	0.4273 (12)	0.4218 (8)	0.878 (3)	*
C29	0.4099 (14)	0.3770 (8)	0.929 (3)	*
C17	0.8011 (15)	0.3254 (8)	0.335 (3)	*
C30	0.4385 (12)	0.3338 (8)	0.894 (3)	*
C31	0.4897 (12)	0.3352 (7)	0.819 (2)	*
C32	0.4987 (12)	0.4744 (9)	0.752 (2)	*
C33	0.4493 (14)	0.4978 (9)	0.675 (2)	*
C34	0.5171 (11)	0.5094 (8)	0.852 (2)	*
C35	0.5223 (12)	0.2876 (8)	0.788 (2)	*
C36	0.4807 (12)	0.2510 (8)	0.726 (2)	*
C37	0.5498 (11)	0.2642 (8)	0.898 (2)	*
H1	0.80273	0.36977	0.63452	*
H2	0.87553	0.37255	0.79426	*
H3	0.83992	0.38567	0.98991	*
H4	0.74619	0.39694	1.12774	*
H5	0.63566	0.40459	1.14665	*
H6	0.56971	0.40008	0.97761	*
H7	0.77919	0.25485	0.38967	*
H8	0.83211	0.31403	0.27445	*
H9	0.80656	0.39862	0.28890	*
H10	0.65634	0.28327	0.59441	*
H11	0.76640	0.22461	0.58515	*
H12	0.75116	0.26574	0.68351	*
H13	0.71101	0.21551	0.67785	*
H14	0.62441	0.24620	0.42087	*
H15	0.68620	0.21209	0.41974	*
H16	0.63330	0.20350	0.51744	*
H17	0.68886	0.44885	0.48102	*
H18	0.79058	0.46276	0.54411	*
H19	0.81327	0.47030	0.41072	*
H20	0.76802	0.51043	0.47085	*
H21	0.73195	0.45969	0.24681	*
H22	0.66150	0.44596	0.28395	*
H23	0.68910	0.50012	0.31176	*
H24	0.40127	0.45159	0.89068	*
H25	0.36719	0.37442	0.96421	*
H26	0.42220	0.30131	0.91827	*
H27	0.53578	0.46870	0.70549	*
H28	0.43986	0.47522	0.61058	*
H29	0.41007	0.50198	0.72382	*
H30	0.46204	0.52997	0.64681	*
H31	0.47990	0.51334	0.90543	*
H32	0.55086	0.49359	0.89863	*
H33	0.52987	0.54112	0.82320	*
H34	0.55903	0.29602	0.73582	*
H35	0.44626	0.24312	0.77591	*
H36	0.46760	0.26601	0.65177	*
H37	0.50485	0.21997	0.70692	*
H38	0.58117	0.28854	0.93443	*
H39	0.51778	0.25752	0.95441	*
H40	0.57413	0.23387	0.88007	*

Geometric parameters (Å, º)

Rh1—C13	1.99 (3)	C21—H13	1.01 (2)
Rh1—N2	2.04 (3)	C22—H15	0.99 (2)
Rh1—N1	2.06 (2)	C22—H16	1.01 (2)
Rh1—Cl1	2.26 (3)	C22—H14	1.03 (2)
N1—C1	1.27 (3)	C23—H17	0.96 (3)
N1—C14	1.45 (3)	C23—C25	1.50 (4)
N2—C11	1.29 (3)	C23—C24	1.52 (4)
N2—C26	1.44 (3)	C24—H20	0.98 (2)
C1—C11	1.38 (3)	C24—H18	1.00 (2)
C1—C2	1.41 (3)	C24—H19	1.04 (3)
C2—C12	1.40 (3)	C25—H23	0.99 (2)
C2—C3	1.42 (3)	C25—H22	1.00 (2)
C3—H1	1.01 (2)	C25—H21	1.06 (3)
C3—C4	1.49 (4)	C26—C27	1.41 (3)
C4—H2	1.01 (3)	C26—C31	1.43 (3)
C4—C5	1.38 (4)	C27—C28	1.41 (4)
C5—H3	0.98 (3)	C27—C32	1.55 (3)
C5—C6	1.46 (6)	C28—H24	1.00 (2)
C6—C12	1.40 (4)	C28—C29	1.42 (4)
C6—C7	1.43 (4)	C29—H25	1.01 (3)
C7—H4	1.03 (3)	C29—C30	1.40 (3)
C7—C8	1.42 (4)	C17—H8	1.02 (3)
C8—H5	1.00 (3)	C30—H26	1.00 (2)
C8—C9	1.39 (4)	C30—C31	1.41 (4)
C9—H6	0.99 (2)	C31—C35	1.53 (3)
C9—C10	1.40 (3)	C32—H27	0.98 (3)
C10—C12	1.38 (3)	C32—C33	1.53 (4)
C10—C11	1.44 (3)	C32—C34	1.55 (4)
C13—O13	1.04 (4)	C33—H30	0.98 (2)
C14—C19	1.41 (3)	C33—H28	0.99 (2)
C14—C15	1.42 (3)	C33—H29	1.03 (3)
C15—C16	1.42 (4)	C34—H33	0.97 (2)
C15—C20	1.56 (3)	C34—H32	1.01 (2)
C16—H7	0.99 (2)	C34—H31	1.02 (3)
C16—C17	1.39 (4)	C35—H34	1.02 (3)
C18—H9	1.02 (2)	C35—C36	1.52 (3)
C18—C17	1.39 (3)	C35—C37	1.55 (4)
C18—C19	1.41 (4)	C36—H35	0.97 (2)
C19—C23	1.57 (3)	C36—H36	1.00 (2)
C20—H10	1.01 (2)	C36—H37	1.02 (2)
C20—C21	1.50 (3)	C37—H39	0.98 (2)
C20—C22	1.53 (3)	C37—H40	1.00 (2)
C21—H11	0.98 (2)	C37—H38	1.04 (2)
C21—H12	1.01 (2)
C37···H14^i	1.67 (2)	C14···C21	3.60 (3)
C22···H38	1.76 (2)	C2···C9	3.60 (3)
C25···H17	2.02 (3)	C6···C11	3.60 (4)
C4···H3	2.04 (3)	C20···C37	3.60 (3)
C24···H17	2.04 (3)	C26···C37	3.60 (3)
C20···H12	2.05 (3)	O13···C14	3.61 (4)
C20···H11	2.05 (2)	C14···C24	3.61 (3)
C35···H35	2.06 (2)	C3···C10	3.62 (3)
C35···H36	2.06 (3)	C26···C34	3.62 (3)
C19···H17	2.06 (2)	C14···C25	3.62 (3)
C22···H10	2.06 (2)	C13···C19	3.63 (4)
C27···H27	2.07 (3)	C9···C27	3.64 (3)
C34···H27	2.07 (3)	C22···C35	3.64 (3)
C33···H27	2.07 (3)	C14···C22	3.64 (3)
C7···H5	2.07 (3)	C26···C33	3.65 (3)
C30···H25	2.07 (3)	C3···C15	3.65 (3)
C32···H28	2.07 (3)	C3···C19	3.65 (3)
C37···H34	2.08 (3)	C11···C14	3.66 (3)
C17···H9	2.08 (2)	C7···C18	3.66 (4)
C10···H6	2.08 (2)	C12···C22^i	3.66 (4)
C20···H13	2.08 (2)	C1···C26	3.66 (3)
C16···H8	2.08 (3)	C9···C31	3.67 (3)
C31···H34	2.08 (2)	C26···C36	3.67 (3)
C8···H6	2.08 (3)	C3···C11	3.67 (3)
C31···H26	2.08 (3)	C1···C9	3.68 (3)
C21···H10	2.09 (2)	C3···C30	3.69 (4)
C23···H22	2.09 (3)	C2···C15	3.70 (3)
C15···H10	2.09 (3)	C2···C7	3.70 (3)
C17···H7	2.09 (2)	C10···C31	3.70 (3)
C29···H26	2.09 (2)	Cl1···C31	3.70 (4)
C9···H5	2.09 (2)	C8···C22^i	3.70 (6)
C32···H29	2.09 (3)	Cl1···C27	3.72 (4)
C23···H18	2.09 (3)	C5···C10	3.72 (3)
C18···H8	2.10 (2)	C10···C27	3.74 (3)
C28···H25	2.10 (3)	N2···C28	3.75 (4)
C15···H7	2.10 (2)	C4···C27	3.76 (4)
C27···H24	2.10 (3)	C2···C19	3.76 (3)
C20···H15	2.10 (2)	N1···C18	3.76 (4)
C23···H23	2.10 (2)	C4···C7	3.77 (4)
C29···H24	2.10 (2)	N2···C30	3.78 (4)
C35···H39	2.10 (3)	N1···C16	3.78 (3)
C32···H30	2.10 (3)	C5···C8	3.80 (4)
C36···H34	2.10 (2)	C8···C11	3.80 (3)
C23···H20	2.11 (2)	Rh1···C35	3.80 (3)
C3···H2	2.11 (2)	Cl1···O13	3.81 (4)
C35···H37	2.11 (2)	N1···O13	3.81 (4)
C6···H4	2.11 (3)	C18···C29	3.82 (4)
C23···H21	2.11 (3)	Rh1···C15	3.83 (3)
C32···H32	2.11 (3)	C29···C35	3.83 (4)
C23···H19	2.11 (3)	Rh1···C31	3.83 (3)
C32···H31	2.11 (3)	C20···C17	3.84 (4)
C19···H9	2.12 (3)	Rh1···C20	3.84 (3)
C32···H33	2.12 (2)	C28···C34	3.85 (4)
C6···H3	2.12 (3)	C1···C4	3.87 (3)
C20···H14	2.12 (3)	C23···C17	3.87 (3)
C2···H1	2.12 (2)	C27···C35	3.87 (3)
C5···H2	2.12 (3)	O13···C35	3.88 (4)
C20···H16	2.13 (2)	C29···C17	3.88 (5)
C35···H38	2.13 (3)	C29···C32	3.88 (4)
C35···H40	2.14 (2)	C19···C20	3.89 (3)
C8···H4	2.15 (3)	C15···C23	3.89 (3)
C4···H1	2.20 (3)	C31···C32	3.89 (3)
C11···C12	2.24 (3)	C9···O13	3.90 (4)
C1···C12	2.24 (3)	C7···C22^i	3.90 (7)
C2···C11	2.27 (3)	O13···C19	3.90 (4)
N1···C11	2.29 (3)	C8···C24	3.91 (6)
C1···C10	2.29 (3)	C13···C36	3.91 (4)
C2···C10	2.29 (3)	O13···C15	3.93 (4)
N2···C1	2.31 (3)	C4···C31	3.93 (4)
C7···C12	2.37 (4)	C2···C20	3.94 (3)
C8···C10	2.39 (3)	Rh1···C37	3.95 (2)
C9···C12	2.40 (3)	C12···C24	3.95 (4)
C1···C14	2.41 (3)	C7···C21^i	3.96 (7)
C11···C26	2.41 (3)	N1···C21	3.96 (3)
C15···C17	2.42 (4)	C13···C22	3.96 (4)
C5···C12	2.42 (3)	C10···C35	3.97 (3)
C16···C18	2.42 (3)	C13···C20	3.97 (4)
C3···C12	2.43 (3)	Rh1···C19	3.97 (3)
C28···C30	2.43 (3)	C9···C34	3.97 (3)
C14···C18	2.43 (4)	N2···C34	3.98 (3)
C26···C28	2.43 (3)	N2···C37	3.98 (3)
N1···C2	2.44 (3)	N1···C24	3.98 (3)
C19···C17	2.44 (4)	C3···C24	3.99 (3)
C29···C31	2.44 (4)	C3···C21	4.00 (3)
C7···C9	2.44 (3)	C6···C22^i	4.00 (10)
C15···C19	2.45 (3)	Rh1···C27	4.00 (3)
C4···C6	2.45 (5)	C9···C37	4.01 (3)
C26···C30	2.46 (3)	N1···C25	4.01 (3)
C14···C16	2.46 (3)	C24···C28	4.02 (4)
C27···C29	2.47 (4)	C8···C13	4.02 (4)
C27···C31	2.47 (3)	N2···C33	4.03 (3)
C6···C10	2.47 (4)	N2···C13	4.03 (4)
C2···C6	2.47 (4)	N1···C22	4.04 (3)
N2···C27	2.47 (3)	C13···C23	4.05 (4)
C6···C8	2.48 (4)	C13···C25	4.05 (4)
N1···C19	2.48 (3)	Cl1···C33	4.05 (3)
N1···C15	2.48 (3)	C2···C23	4.05 (3)
C22···C37	2.48 (3)	C10···C32	4.06 (3)
N2···C10	2.49 (3)	C4···C26	4.06 (3)
C2···C4	2.49 (3)	C10···C37	4.06 (3)
N2···C31	2.49 (3)	Cl1···C36	4.06 (3)
C24···C25	2.50 (4)	N1···C26	4.06 (3)
C21···C22	2.50 (3)	N2···C14	4.07 (3)
C3···C5	2.50 (4)	Cl1···C35	4.07 (3)
C36···C37	2.51 (3)	C2···C21	4.07 (4)
C31···C37	2.51 (3)	N2···C36	4.08 (3)
C15···C21	2.52 (3)	Cl1···C32	4.10 (3)
C19···C25	2.53 (3)	C11···C37	4.10 (3)
C30···C35	2.54 (4)	C1···C21	4.11 (3)
C19···C24	2.54 (3)	C36···C37	4.12 (4)
C27···C34	2.54 (3)	O13···C25	4.12 (4)
C33···C34	2.54 (4)	C2···C8	4.13 (3)
C5···C7	2.54 (4)	C18···C21	4.13 (3)
C31···C36	2.55 (3)	C24···C29	4.13 (4)
C15···C22	2.55 (3)	C1···C13	4.14 (4)
C16···C20	2.55 (4)	C13···C35	4.14 (4)
C27···C33	2.56 (3)	C19···C29	4.15 (4)
C28···C32	2.57 (4)	C7···O13	4.15 (5)
C26···C32	2.58 (3)	Rh1···C23	4.15 (3)
C26···C35	2.58 (3)	C9···C32	4.15 (3)
C18···C23	2.58 (3)	C3···C23	4.16 (3)
C14···C20	2.59 (3)	C3···C20	4.16 (3)
C14···C23	2.59 (3)	C4···C10	4.16 (3)
C1···C3	2.61 (3)	Rh1···C32	4.16 (3)
C9···C11	2.62 (3)	Rh1···C2	4.17 (2)
N1···N2	2.64 (3)	C23···C33	4.18 (4)
C8···C12	2.74 (4)	C13···C33	4.18 (4)
Rh1···C11	2.77 (2)	O13···C22	4.19 (4)
Rh1···C1	2.77 (2)	C7···C11	4.19 (3)
C4···C12	2.78 (3)	C11···C22^i	4.19 (3)
C7···C10	2.79 (3)	Rh1···C10	4.20 (3)
C15···C18	2.79 (3)	C9···C35	4.20 (3)
C14···C17	2.81 (4)	C9···C24	4.20 (3)
C28···C31	2.81 (3)	C11···C34	4.20 (3)
C26···C29	2.83 (4)	C1···C24	4.21 (3)
C27···C30	2.84 (3)	C10···C34	4.21 (3)
C16···C19	2.84 (3)	C7···C19	4.21 (4)
C2···C5	2.86 (4)	C10···C24	4.21 (4)
C3···C6	2.87 (4)	C15···C21	4.21 (3)
C6···C9	2.87 (3)	C7···C17	4.22 (5)
N2···C32	2.92 (3)	C1···C5	4.22 (4)
N1···C20	2.95 (3)	C2···C24	4.23 (3)
N1···C23	2.95 (3)	C6···C25	4.23 (10)
N2···C35	2.95 (3)	N1···C17	4.26 (4)
N1···C13	2.97 (4)	Cl1···C37	4.26 (3)
Rh1···O13	3.03 (3)	N2···C29	4.27 (4)
C2···C14	3.04 (3)	C4···C33	4.27 (5)
Cl1···C13	3.05 (4)	C9···C28	4.27 (3)
C10···C26	3.05 (3)	C3···C7	4.27 (3)
C30···C37	3.08 (3)	C5···C9	4.28 (3)
C16···C21	3.09 (4)	C2···C22^i	4.29 (3)
Rh1···C14	3.09 (3)	C8···C21^i	4.29 (6)
Rh1···C26	3.10 (3)	Cl1···N1	4.30 (3)
C13···C14	3.10 (4)	Rh1···C22	4.31 (3)
C16···C22	3.10 (3)	C9···C30	4.31 (3)
C28···C34	3.11 (3)	C11···C20	4.31 (3)
C30···C36	3.12 (4)	C1···C35	4.31 (3)
C18···C25	3.12 (3)	C29···C34	4.32 (4)
C18···C24	3.13 (3)	C8···C18	4.32 (4)
C3···C29	3.14 (4)	C16···C29	4.32 (4)
Cl1···N2	3.15 (3)	C15···C37	4.32 (3)
C28···C33	3.17 (4)	C6···C23	4.33 (11)
C3···C14	3.23 (3)	Rh1···C36	4.34 (3)
C8···O13	3.23 (5)	O13···C21	4.34 (4)
Cl1···C26	3.23 (3)	C28···C35	4.34 (3)
C9···C26	3.24 (3)	C12···C26	4.34 (3)
N1···C3	3.25 (3)	C17···C30	4.34 (4)
C13···C37	3.28 (4)	C24···C25	4.35 (4)
C1···C15	3.28 (3)	C29···C37	4.35 (3)
N2···C9	3.29 (3)	C18···C20	4.35 (3)
C11···C31	3.29 (3)	C3···C16	4.35 (3)
C11···C27	3.32 (3)	C9···C34	4.35 (3)
C1···C19	3.32 (3)	C3···C27	4.36 (4)
C21···C17^i	3.32 (4)	C12···C14	4.36 (3)
C4···C29	3.33 (5)	C3···C18	4.36 (3)
C16···C21	3.34 (4)	Cl1···C11	4.36 (3)
C4···C28	3.35 (4)	C6···C21^i	4.36 (10)
C25···C33	3.36 (4)	C5···C21^i	4.37 (6)
O13···C37	3.38 (4)	O13···C22	4.37 (4)
C3···C28	3.46 (4)	C21···C22^i	4.38 (3)
C7···C25	3.47 (5)	C21···C17	4.38 (4)
Cl1···C5	3.47 (4)	C30···C32	4.39 (3)
C8···C25	3.48 (5)	O13···C23	4.39 (4)
N2···C2	3.48 (3)	C22···C17	4.40 (4)
N1···C10	3.48 (3)	C5···C24	4.40 (7)
C1···C20	3.49 (3)	C27···C34	4.40 (4)
N1···C12	3.49 (3)	C29···C34	4.40 (3)
C11···C35	3.50 (3)	C22···C31	4.40 (3)
C6···C24	3.51 (11)	C16···C23	4.41 (3)
N2···C12	3.51 (3)	O13···C33	4.41 (4)
O13···C36	3.52 (4)	C24···C17	4.41 (3)
Cl1···C4	3.54 (4)	Rh1···C33	4.42 (3)
C34···C34	3.55 (4)	C25···C17	4.43 (3)
C4···C30	3.55 (4)	Cl1···C30	4.56 (4)
C10···C22^i	3.56 (4)	Cl1···C28	4.56 (4)
C11···C32	3.56 (3)	Cl1···C36	4.64 (3)
C1···C23	3.56 (3)	Rh1···C25	4.65 (3)
C7···C24	3.57 (7)	Cl1···C33	4.66 (3)
C9···C22^i	3.58 (3)	Rh1···C33	4.71 (3)
C1···C6	3.59 (4)	Rh1···C12	4.81 (2)
C13···C15	3.60 (4)
C13—Rh1—N2	174.2 (12)	H16—C22—H14	106 (2)
C13—Rh1—N1	94.3 (11)	H16—C22—C20	112 (2)
C13—Rh1—Cl1	91.4 (10)	H14—C22—C20	110 (2)
N2—Rh1—N1	80.0 (10)	H17—C23—C25	108 (2)
N2—Rh1—Cl1	94.2 (9)	H17—C23—C24	108 (2)
N1—Rh1—Cl1	174.0 (10)	H17—C23—C19	107 (2)
C1—N1—C14	125 (2)	C25—C23—C24	111 (2)
C1—N1—Rh1	111.0 (17)	C25—C23—C19	111 (2)
C14—N1—Rh1	122.9 (16)	C24—C23—C19	110 (2)
C11—N2—C26	124 (2)	H20—C24—H18	111 (2)
C11—N2—Rh1	110.3 (17)	H20—C24—H19	107 (2)
C26—N2—Rh1	124.6 (17)	H20—C24—C23	113 (2)
N1—C1—C11	119 (2)	H18—C24—H19	106 (2)
N1—C1—C2	132 (2)	H18—C24—C23	110 (2)
C11—C1—C2	108.6 (19)	H19—C24—C23	110 (2)
C12—C2—C1	106.3 (19)	H23—C25—H22	111 (2)
C12—C2—C3	118.8 (18)	H23—C25—H21	106 (2)
C1—C2—C3	134.8 (19)	H23—C25—C23	114 (2)
H1—C3—C2	120 (2)	H22—C25—H21	105 (2)
H1—C3—C4	122 (2)	H22—C25—C23	112 (2)
C2—C3—C4	117.5 (18)	H21—C25—C23	110 (2)
H2—C4—C5	125 (3)	C27—C26—C31	120 (2)
H2—C4—C3	114 (3)	C27—C26—N2	119.6 (18)
C5—C4—C3	121 (2)	C31—C26—N2	120.2 (18)
H3—C5—C4	118 (3)	C28—C27—C26	119 (2)
H3—C5—C6	118 (4)	C28—C27—C32	120 (2)
C4—C5—C6	119 (3)	C26—C27—C32	121 (2)
C12—C6—C7	114 (3)	H24—C28—C27	119 (2)
C12—C6—C5	115 (5)	H24—C28—C29	119 (3)
C7—C6—C5	123 (4)	C27—C28—C29	121 (2)
H4—C7—C8	121 (2)	H25—C29—C30	118 (2)
H4—C7—C6	117 (3)	H25—C29—C28	118 (2)
C8—C7—C6	121 (2)	C30—C29—C28	119 (3)
H5—C8—C9	122 (3)	H8—C17—C18	120 (3)
H5—C8—C7	117 (3)	H8—C17—C16	118 (2)
C9—C8—C7	121 (2)	C18—C17—C16	121 (3)
H6—C9—C8	121 (2)	H26—C30—C29	121 (3)
H6—C9—C10	120 (2)	H26—C30—C31	119 (2)
C8—C9—C10	119 (2)	C29—C30—C31	121 (2)
C12—C10—C9	119 (2)	C30—C31—C26	119 (2)
C12—C10—C11	105.2 (19)	C30—C31—C35	119 (2)
C9—C10—C11	135.5 (19)	C26—C31—C35	121 (2)
N2—C11—C1	119 (2)	H27—C32—C33	109 (2)
N2—C11—C10	131 (2)	H27—C32—C27	108 (2)
C1—C11—C10	108.7 (18)	H27—C32—C34	107 (2)
C10—C12—C2	111 (2)	C33—C32—C27	113 (2)
C10—C12—C6	125 (2)	C33—C32—C34	111 (2)
C2—C12—C6	124 (2)	C27—C32—C34	110 (2)
O13—C13—Rh1	178 (3)	H30—C33—H28	112 (2)
C19—C14—C15	120 (2)	H30—C33—H29	109 (2)
C19—C14—N1	120.2 (17)	H30—C33—C32	112 (2)
C15—C14—N1	120 (2)	H28—C33—H29	108 (3)
C14—C15—C16	121 (2)	H28—C33—C32	109 (2)
C14—C15—C20	121 (2)	H29—C33—C32	108 (2)
C16—C15—C20	118.2 (19)	H33—C34—H32	111 (2)
H7—C16—C17	121 (3)	H33—C34—H31	110 (2)
H7—C16—C15	120 (2)	H33—C34—C32	112 (2)
C17—C16—C15	119 (2)	H32—C34—H31	107 (2)
H9—C18—C17	118 (3)	H32—C34—C32	109 (2)
H9—C18—C19	120 (2)	H31—C34—C32	108 (2)
C17—C18—C19	121 (2)	H34—C35—C36	110 (2)
C18—C19—C14	119 (2)	H34—C35—C31	108 (2)
C18—C19—C23	120 (2)	H34—C35—C37	106 (2)
C14—C19—C23	121 (2)	C36—C35—C31	113 (2)
H10—C20—C21	110 (2)	C36—C35—C37	109.8 (18)
H10—C20—C22	107 (2)	C31—C35—C37	110 (2)
H10—C20—C15	106.4 (18)	H35—C36—H36	113 (2)
C21—C20—C22	111.1 (18)	H35—C36—H37	110 (2)
C21—C20—C15	111 (2)	H35—C36—C35	109 (2)
C22—C20—C15	111 (2)	H36—C36—H37	107 (2)
H11—C21—H12	111 (2)	H36—C36—C35	108 (2)
H11—C21—H13	110 (2)	H37—C36—C35	110 (2)
H11—C21—C20	110 (2)	H39—C37—H40	111 (2)
H12—C21—H13	108 (2)	H39—C37—H38	108 (2)
H12—C21—C20	108.2 (19)	H39—C37—C35	111 (2)
H13—C21—C20	110 (2)	H40—C37—H38	105 (2)
H15—C22—H16	109 (2)	H40—C37—C35	112 (2)
H15—C22—H14	108 (2)	H38—C37—C35	108.9 (19)
H15—C22—C20	111 (2)
Cl1—Rh1—N1—C1	16 (11)	H9—C18—C17—H8	−6 (5)
Cl1—Rh1—N1—C14	−174 (9)	C14—C19—C23—C24	117 (3)
N2—Rh1—N1—C1	−0.0 (18)	C14—C19—C23—C25	−119 (3)
N2—Rh1—N1—C14	170.6 (18)	C14—C19—C23—H17	0 (3)
C13—Rh1—N1—C1	179 (2)	C18—C19—C23—C24	−63 (3)
C13—Rh1—N1—C14	−10 (2)	C18—C19—C23—C25	61 (3)
Cl1—Rh1—N2—C11	−178.7 (18)	C18—C19—C23—H17	179 (2)
Cl1—Rh1—N2—C26	13.7 (19)	C15—C20—C21—H11	−60 (3)
N1—Rh1—N2—C11	−0.3 (18)	C15—C20—C21—H12	61 (3)
N1—Rh1—N2—C26	−168.0 (19)	C15—C20—C21—H13	178 (2)
C13—Rh1—N2—C11	−9 (13)	C22—C20—C21—H11	64 (3)
C13—Rh1—N2—C26	−177 (12)	C22—C20—C21—H12	−175 (2)
Cl1—Rh1—C13—O13	6 (91)	C22—C20—C21—H13	−57 (3)
N1—Rh1—C13—O13	−172 (91)	H10—C20—C21—H11	−178 (2)
N2—Rh1—C13—O13	−163 (84)	H10—C20—C21—H12	−57 (3)
Rh1—N1—C1—C2	172 (3)	H10—C20—C21—H13	61 (3)
Rh1—N1—C1—C11	0 (3)	C15—C20—C22—H14	−60 (3)
C14—N1—C1—C2	1 (4)	C15—C20—C22—H15	60 (3)
C14—N1—C1—C11	−170 (2)	C15—C20—C22—H16	−178 (2)
Rh1—N1—C14—C15	−82 (3)	C21—C20—C22—H14	176 (2)
Rh1—N1—C14—C19	98 (2)	C21—C20—C22—H15	−64 (3)
C1—N1—C14—C15	87 (3)	C21—C20—C22—H16	58 (3)
C1—N1—C14—C19	−93 (3)	H10—C20—C22—H14	55 (3)
Rh1—N2—C11—C1	0 (3)	H10—C20—C22—H15	175 (2)
Rh1—N2—C11—C10	−171 (2)	H10—C20—C22—H16	−62 (3)
C26—N2—C11—C1	168 (2)	C19—C23—C24—H18	−57 (3)
C26—N2—C11—C10	−3 (4)	C19—C23—C24—H19	59 (3)
Rh1—N2—C26—C27	−101 (2)	C19—C23—C24—H20	178 (2)
Rh1—N2—C26—C31	80 (3)	C25—C23—C24—H18	178 (2)
C11—N2—C26—C27	93 (3)	C25—C23—C24—H19	−65 (3)
C11—N2—C26—C31	−87 (3)	C25—C23—C24—H20	54 (3)
N1—C1—C2—C3	5 (6)	H17—C23—C24—H18	59 (3)
N1—C1—C2—C12	−172 (3)	H17—C23—C24—H19	175 (2)
C11—C1—C2—C3	177 (3)	H17—C23—C24—H20	−65 (3)
C11—C1—C2—C12	0 (3)	C19—C23—C25—H21	−59 (3)
N1—C1—C11—N2	0 (4)	C19—C23—C25—H22	57 (3)
N1—C1—C11—C10	173 (2)	C19—C23—C25—H23	−177 (2)
C2—C1—C11—N2	−174 (2)	C24—C23—C25—H21	65 (3)
C2—C1—C11—C10	0 (3)	C24—C23—C25—H22	−179 (2)
C1—C2—C3—C4	−173 (4)	C24—C23—C25—H23	−53 (3)
C1—C2—C3—H1	3 (5)	H17—C23—C25—H21	−176 (2)
C12—C2—C3—C4	4 (5)	H17—C23—C25—H22	−60 (3)
C12—C2—C3—H1	−179 (3)	H17—C23—C25—H23	66 (3)
C1—C2—C12—C6	−172 (6)	N2—C26—C27—C28	−176 (2)
C1—C2—C12—C10	1 (4)	N2—C26—C27—C32	3 (4)
C3—C2—C12—C6	10 (7)	C31—C26—C27—C28	4 (4)
C3—C2—C12—C10	−177 (3)	C31—C26—C27—C32	−177 (2)
C2—C3—C4—C5	−3 (7)	N2—C26—C31—C30	176 (2)
C2—C3—C4—H2	−173 (4)	N2—C26—C31—C35	−3 (4)
H1—C3—C4—C5	−179 (5)	C27—C26—C31—C30	−4 (4)
H1—C3—C4—H2	10 (6)	C27—C26—C31—C35	178 (2)
C3—C4—C5—C6	−12 (*)	C26—C27—C28—C29	2 (4)
C3—C4—C5—H3	−167 (5)	C26—C27—C28—H24	−174 (3)
H2—C4—C5—C6	158 (7)	C32—C27—C28—C29	−176 (3)
H2—C4—C5—H3	2 (11)	C32—C27—C28—H24	8 (4)
C4—C5—C6—C7	171 (7)	C26—C27—C32—C33	118 (3)
C4—C5—C6—C12	24 (11)	C26—C27—C32—C34	−118 (3)
H3—C5—C6—C7	−33 (13)	C26—C27—C32—H27	−2 (4)
H3—C5—C6—C12	−180 (6)	C28—C27—C32—C33	−63 (3)
C5—C6—C7—C8	−157 (7)	C28—C27—C32—C34	61 (3)
C5—C6—C7—H4	16 (13)	C28—C27—C32—H27	177 (3)
C12—C6—C7—C8	−9 (12)	C27—C28—C29—C30	−8 (5)
C12—C6—C7—H4	163 (7)	C27—C28—C29—H25	−163 (3)
C5—C6—C12—C2	−24 (10)	H24—C28—C29—C30	168 (3)
C5—C6—C12—C10	164 (5)	H24—C28—C29—H25	13 (5)
C7—C6—C12—C2	−174 (6)	C28—C29—C30—C31	8 (5)
C7—C6—C12—C10	14 (11)	C28—C29—C30—H26	−169 (3)
C6—C7—C8—C9	1 (10)	H25—C29—C30—C31	163 (3)
C6—C7—C8—H5	−175 (7)	H25—C29—C30—H26	−14 (5)
H4—C7—C8—C9	−171 (6)	C29—C30—C31—C26	−2 (4)
H4—C7—C8—H5	13 (*)	C29—C30—C31—C35	176 (3)
C7—C8—C9—C10	4 (7)	H26—C30—C31—C26	175 (3)
C7—C8—C9—H6	−176 (5)	H26—C30—C31—C35	−6 (4)
H5—C8—C9—C10	179 (4)	C26—C31—C35—C36	−121 (3)
H5—C8—C9—H6	0 (7)	C26—C31—C35—C37	116 (3)
C8—C9—C10—C11	179 (4)	C26—C31—C35—H34	1 (4)
C8—C9—C10—C12	0 (5)	C30—C31—C35—C36	61 (3)
H6—C9—C10—C11	−2 (5)	C30—C31—C35—C37	−62 (3)
H6—C9—C10—C12	180 (3)	C30—C31—C35—H34	−177 (2)
C9—C10—C11—N2	−5 (5)	C27—C32—C33—H28	−59 (3)
C9—C10—C11—C1	−177 (3)	C27—C32—C33—H29	58 (3)
C12—C10—C11—N2	174 (3)	C27—C32—C33—H30	177 (2)
C12—C10—C11—C1	1 (3)	C34—C32—C33—H28	178 (2)
C9—C10—C12—C2	177 (3)	C34—C32—C33—H29	−65 (3)
C9—C10—C12—C6	−10 (7)	C34—C32—C33—H30	54 (3)
C11—C10—C12—C2	−2 (4)	H27—C32—C33—H28	60 (3)
C11—C10—C12—C6	171 (6)	H27—C32—C33—H29	177 (2)
N1—C14—C15—C16	−178 (2)	H27—C32—C33—H30	−63 (3)
N1—C14—C15—C20	2 (3)	C27—C32—C34—H31	−59 (3)
C19—C14—C15—C16	2 (4)	C27—C32—C34—H32	57 (3)
C19—C14—C15—C20	−178 (2)	C27—C32—C34—H33	−180 (2)
N1—C14—C19—C18	179 (2)	C33—C32—C34—H31	66 (3)
N1—C14—C19—C23	−1 (4)	C33—C32—C34—H32	−178 (2)
C15—C14—C19—C18	0 (4)	C33—C32—C34—H33	−55 (3)
C15—C14—C19—C23	179 (2)	H27—C32—C34—H31	−175 (2)
C14—C15—C16—C17	0 (4)	H27—C32—C34—H32	−59 (3)
C14—C15—C16—H7	−176 (2)	H27—C32—C34—H33	64 (3)
C20—C15—C16—C17	180 (3)	C31—C35—C36—H35	−60 (3)
C20—C15—C16—H7	5 (4)	C31—C35—C36—H36	63 (3)
C14—C15—C20—C21	−117 (2)	C31—C35—C36—H37	179 (2)
C14—C15—C20—C22	119 (2)	C37—C35—C36—H35	64 (3)
C14—C15—C20—H10	3 (3)	C37—C35—C36—H36	−174 (2)
C16—C15—C20—C21	63 (3)	C37—C35—C36—H37	−57 (3)
C16—C15—C20—C22	−61 (3)	H34—C35—C36—H35	180 (2)
C16—C15—C20—H10	−177 (2)	H34—C35—C36—H36	−58 (3)
C15—C16—C17—C18	−2 (4)	H34—C35—C36—H37	59 (3)
C15—C16—C17—H8	−174 (3)	C31—C35—C37—H38	−60 (3)
H7—C16—C17—C18	173 (3)	C31—C35—C37—H39	59 (3)
H7—C16—C17—H8	0 (5)	C31—C35—C37—H40	−176 (2)
C17—C18—C19—C14	−2 (4)	C36—C35—C37—H38	175 (2)
C17—C18—C19—C23	178 (3)	C36—C35—C37—H39	−66 (3)
H9—C18—C19—C14	179 (2)	C36—C35—C37—H40	59 (3)
H9—C18—C19—C23	0 (4)	H34—C35—C37—H38	57 (3)
C19—C18—C17—C16	4 (5)	H34—C35—C37—H39	175 (2)
C19—C18—C17—H8	176 (3)	H34—C35—C37—H40	−60 (3)
H9—C18—C17—C16	−178 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

(Compound_2) tetrahydrofurfuryl-(N,N'-ethylene-bis(3-methyl-salicylideneiminato –N,N',O,O')-cobalt

Crystal data

C23H27CoN2O3	β = 96.520 (3)°
Mr = 438.41	V = 2138.1 (2) Å^3
Monoclinic, P21/n	Z = 4
Hall symbol: -p 2yn	Synchrotron radiation, λ = 0.65051 Å
a = 16.6701 (6) Å	µ = 0.8 mm^−1
b = 9.4170 (4) Å	T = 293 K
c = 13.7088 (7) Å	cylinder, ? × 0.7 mm mm

Data collection

ESRF BM16 diffractometer	Data collection mode: transmission
Radiation source: synchrotron	Scan method: continuous
Specimen mounting: capillary	2θmin = 0.010°, 2θmax = 30.00°, 2θstep = 0.005°

Refinement

Rp = 8.5	142 parameters
Rwp = 11.4	Calculated and kept fixed
Rexp = ?
χ^2 = 57.760	Background function: polynomal
5999 data points	Preferred orientation correction: 'Ahtee and Jarvinen'
Profile function: split-type pseudo-Voigt

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

	x	y	z	Biso*/Beq
Co	0.5091 (7)	0.6512 (9)	0.4239 (9)	*
O1	0.531 (3)	0.551 (5)	0.315 (3)	*
O2	0.395 (3)	0.637 (5)	0.377 (4)	*
O3	0.540 (4)	0.932 (5)	0.193 (3)	*
N1	0.616 (4)	0.677 (5)	0.475 (4)	*
N2	0.486 (4)	0.750 (5)	0.542 (5)	*
C1	0.599 (5)	0.502 (8)	0.294 (5)	*
C2	0.671 (4)	0.526 (9)	0.353 (5)	*
C3	0.676 (4)	0.600 (7)	0.448 (5)	*
C4	0.337 (4)	0.724 (8)	0.415 (5)	*
C5	0.349 (4)	0.796 (7)	0.504 (5)	*
C6	0.423 (4)	0.802 (7)	0.561 (5)	*
C7	0.562 (5)	0.754 (7)	0.615 (5)	*
C8	0.630 (5)	0.764 (6)	0.562 (5)	*
C9	0.603 (5)	0.433 (8)	0.203 (6)	*
C10	0.679 (5)	0.383 (7)	0.177 (5)	*
C11	0.748 (5)	0.438 (8)	0.238 (7)	*
C12	0.741 (5)	0.496 (8)	0.325 (5)	*
C13	0.534 (4)	0.387 (7)	0.138 (4)	*
C14	0.253 (5)	0.698 (8)	0.377 (5)	*
C15	0.190 (4)	0.745 (7)	0.424 (5)	*
C16	0.206 (4)	0.827 (7)	0.511 (5)	*
C17	0.285 (4)	0.863 (7)	0.543 (5)	*
C18	0.242 (5)	0.623 (7)	0.278 (6)	*
C19	0.504 (5)	0.834 (6)	0.343 (5)	*
C20	0.519 (5)	0.801 (7)	0.240 (4)	*
C21	0.508 (5)	0.917 (6)	0.097 (5)	*
C22	0.463 (4)	0.783 (5)	0.076 (5)	*
C23	0.449 (5)	0.740 (6)	0.179 (5)	*
H1	0.72884	0.61379	0.48906	*
H2	0.43276	0.90214	0.60771	*
H3	0.55768	0.84416	0.65820	*
H4	0.56422	0.67196	0.65380	*
H5	0.63725	0.87313	0.53487	*
H6	0.68218	0.74487	0.60020	*
H7	0.68471	0.34137	0.11580	*
H8	0.80489	0.39637	0.22219	*
H9	0.79623	0.51885	0.37329	*
H10	0.49656	0.33205	0.17186	*
H11	0.50302	0.48493	0.11774	*
H12	0.53528	0.34401	0.07094	*
H13	0.13313	0.73514	0.39212	*
H14	0.15992	0.85422	0.54692	*
H15	0.29630	0.90654	0.61220	*
H16	0.26695	0.69110	0.22854	*
H17	0.26302	0.53630	0.28082	*
H18	0.18150	0.62065	0.24375	*
H19	0.45160	0.86780	0.33850	*
H20	0.54797	0.88792	0.37344	*
H21	0.57209	0.73194	0.23607	*
H22	0.47607	0.99620	0.06920	*
H23	0.55818	0.91210	0.04944	*
H24	0.40989	0.79650	0.03228	*
H25	0.49384	0.70628	0.03658	*
H26	0.40026	0.76273	0.19330	*
H27	0.45486	0.62278	0.17759	*

Geometric parameters (Å, º)

Co—O1	1.83 (5)	C10—C11	1.43 (11)
Co—N1	1.86 (6)	C11—H8	1.08 (9)
Co—N2	1.94 (6)	C11—C12	1.34 (12)
Co—O2	1.95 (5)	C12—H9	1.09 (8)
Co—C19	2.05 (6)	C13—H10	0.97 (7)
O1—C1	1.30 (9)	C13—H12	1.00 (6)
O2—C4	1.40 (9)	C13—H11	1.07 (6)
O3—C21	1.36 (8)	C14—C15	1.37 (11)
O3—C20	1.45 (8)	C14—C18	1.52 (10)
N1—C3	1.31 (9)	C15—H13	1.01 (6)
N1—C8	1.44 (9)	C15—C16	1.42 (9)
N2—C6	1.22 (10)	C16—H14	0.99 (8)
N2—C7	1.52 (9)	C16—C17	1.38 (10)
C1—C2	1.38 (10)	C17—H15	1.03 (7)
C1—C9	1.42 (11)	C18—H17	0.88 (7)
C2—C12	1.31 (11)	C18—H16	1.05 (8)
C2—C3	1.46 (10)	C18—H18	1.07 (8)
C3—H1	1.00 (6)	C19—H19	0.93 (8)
C4—C5	1.39 (10)	C19—H20	0.95 (7)
C4—C14	1.46 (11)	C19—C20	1.49 (9)
C5—C6	1.39 (9)	C20—H21	1.10 (8)
C5—C17	1.40 (10)	C20—C23	1.48 (10)
C6—H2	1.14 (7)	C21—H22	0.97 (7)
C7—H4	0.94 (7)	C21—H23	1.12 (9)
C7—H3	1.04 (7)	C21—C22	1.48 (9)
C7—C8	1.42 (11)	C22—H24	1.01 (7)
C8—H6	0.98 (7)	C22—H25	1.07 (6)
C8—H5	1.10 (6)	C22—C23	1.52 (10)
C9—C13	1.43 (10)	C23—H26	0.88 (8)
C9—C10	1.44 (11)	C23—H27	1.11 (6)
C10—H7	0.94 (7)
N1···H1	1.95 (6)	C1···C19	3.60 (10)
C20···H19	1.96 (7)	C5···C19	3.61 (11)
N2···H2	1.96 (6)	C6···C16	3.61 (10)
C8···H4	1.96 (8)	O2···N1	3.61 (7)
C9···H11	1.98 (7)	C10···C16	3.61 (10)
O3···H22	1.99 (5)	N1···C20	3.63 (8)
C9···H10	2.01 (7)	O1···C10	3.65 (9)
C20···H20	2.01 (6)	C2···C5	3.65 (10)
C22···H22	2.02 (5)	N2···C1	3.67 (10)
C22···H26	2.03 (7)	C13···C23	3.68 (9)
O3···H21	2.03 (4)	C19···C22	3.68 (9)
O3···H23	2.03 (5)	O2···C15	3.68 (8)
C8···H3	2.03 (8)	C11···C13	3.70 (11)
N2···H4	2.03 (6)	C6···C14	3.70 (10)
C14···H17	2.03 (7)	C2···C6	3.71 (10)
N1···H6	2.04 (6)	C5···C7	3.72 (10)
N1···H5	2.04 (5)	C7···C18	3.73 (10)
C7···H6	2.04 (8)	O3···C12	3.74 (10)
C20···H26	2.05 (8)	O2···C17	3.74 (9)
C16···H15	2.06 (7)	N1···C6	3.75 (10)
C22···H23	2.07 (7)	C2···C8	3.75 (10)
C14···H13	2.07 (8)	C21···C22	3.75 (9)
C22···H27	2.07 (6)	O2···C7	3.76 (8)
C14···H16	2.07 (7)	C2···C13	3.76 (9)
C11···H7	2.08 (8)	C5···C18	3.76 (10)
N2···H3	2.08 (6)	C3···C19	3.77 (9)
C2···H9	2.08 (7)	O1···C6	3.77 (8)
C15···H14	2.08 (7)	O1···N2	3.77 (8)
C5···H15	2.09 (7)	C3···C9	3.79 (10)
C12···H8	2.09 (8)	C9···C20	3.79 (10)
C7···H5	2.09 (7)	C3···C14	3.79 (9)
C11···H9	2.09 (9)	Co···N2	3.80 (5)
C17···H14	2.09 (7)	O2···N1	3.81 (7)
C9···H7	2.10 (8)	C11···C16	3.81 (11)
C21···H24	2.10 (8)	C3···C5	3.82 (9)
C16···H13	2.11 (7)	C2···C20	3.82 (10)
C23···H24	2.11 (7)	C7···C19	3.82 (9)
C23···H21	2.11 (7)	C12···C16	3.82 (10)
C10···H8	2.12 (7)	N2···C3	3.82 (10)
C20···H27	2.12 (7)	C6···C19	3.82 (9)
C5···H2	2.13 (7)	C16···C18	3.83 (10)
C21···H25	2.15 (6)	C9···C23	3.85 (10)
C2···H1	2.16 (7)	C12···C17	3.88 (10)
O1···H21	2.17 (5)	C10···C12	3.88 (11)
C19···H21	2.17 (7)	O2···C8	3.90 (8)
C9···H12	2.18 (7)	C4···C23	3.92 (11)
C14···H18	2.19 (7)	C1···C7	3.92 (11)
C23···H25	2.19 (7)	O2···C1	3.93 (9)
C20···C21	2.23 (9)	O1···O3	3.97 (6)
C21···C23	2.30 (10)	C2···C4	3.97 (10)
C2···C11	2.31 (12)	C13···C15	3.97 (9)
C3···C12	2.32 (11)	C13···C22	3.97 (8)
N2···C5	2.33 (9)	C2···C17	3.97 (10)
N1···C7	2.33 (10)	C1···C5	3.97 (10)
O1···C9	2.34 (9)	C6···C9	3.98 (10)
O1···C2	2.34 (9)	O1···C4	3.99 (9)
C20···C22	2.35 (9)	O1···C22	4.00 (8)
C1···C12	2.35 (11)	C18···C23	4.00 (12)
O3···C23	2.35 (8)	C2···C19	4.00 (10)
C6···C17	2.36 (10)	C9···C16	4.00 (11)
N2···C8	2.38 (10)	Co···C7	4.01 (7)
C3···C8	2.38 (10)	C5···C12	4.01 (10)
C6···C7	2.39 (10)	O1···C11	4.02 (11)
O3···C19	2.39 (8)	Co···O2	4.05 (5)
O3···C22	2.39 (8)	N2···C2	4.06 (10)
C5···C14	2.41 (10)	Co···N1	4.07 (6)
C2···C9	2.41 (10)	C11···C20	4.07 (12)
C9···C11	2.41 (11)	C7···C19	4.09 (9)
C15···C17	2.41 (9)	C3···C10	4.10 (10)
C14···C16	2.41 (10)	C3···C20	4.10 (9)
C5···C16	2.41 (10)	N1···C4	4.11 (9)
C10···C12	2.42 (10)	O1···C8	4.11 (8)
O2···C14	2.42 (10)	C8···C17	4.11 (10)
C10···C13	2.42 (10)	Co···C9	4.11 (8)
C4···C17	2.43 (10)	C3···C6	4.12 (9)
N1···C2	2.43 (10)	C7···C13	4.13 (10)
C4···C6	2.44 (10)	C4···C20	4.15 (11)
Co···H20	2.443 (9)	C6···C15	4.15 (9)
C1···C10	2.47 (11)	C13···C20	4.16 (9)
C4···C15	2.48 (10)	C12···C15	4.17 (9)
O2···C5	2.48 (9)	Co···O1	4.17 (5)
Co···H19	2.489 (10)	O2···C7	4.19 (8)
C19···C23	2.49 (9)	C12···C13	4.19 (10)
C4···C18	2.50 (10)	O3···C6	4.19 (8)
C1···C3	2.51 (9)	Co···O3	4.20 (5)
C1···C13	2.53 (9)	C11···C17	4.21 (11)
C15···C18	2.54 (10)	C3···C15	4.21 (9)
N1···N2	2.55 (9)	O3···C21	4.21 (8)
O1···C20	2.57 (8)	O2···C16	4.21 (9)
O1···O2	2.64 (8)	N2···C19	4.22 (8)
O2···C19	2.68 (9)	C2···C16	4.22 (10)
O1···C19	2.73 (7)	C12···C17	4.23 (10)
O2···C18	2.74 (9)	C2···C10	4.24 (11)
C1···C11	2.74 (12)	O2···N2	4.24 (7)
O1···N1	2.74 (7)	C11···C16	4.24 (11)
C9···C12	2.76 (10)	C3···C10	4.24 (10)
C14···C17	2.76 (9)	C11···C12	4.25 (11)
C2···C10	2.79 (10)	O2···C2	4.26 (9)
O2···N2	2.79 (8)	Co···C14	4.26 (8)
C5···C15	2.79 (9)	C5···C8	4.26 (9)
Co···C3	2.80 (7)	C10···C22	4.26 (9)
Co···C8	2.81 (7)	N2···C3	4.27 (9)
O1···C23	2.81 (8)	N2···C20	4.27 (9)
Co···C1	2.83 (8)	C12···C21	4.27 (12)
Co···C7	2.83 (7)	C17···C18	4.27 (10)
C4···C16	2.84 (11)	N2···C14	4.29 (10)
N1···C19	2.86 (8)	C7···C9	4.29 (11)
Co···C6	2.87 (7)	C9···C22	4.29 (9)
N2···C4	2.87 (9)	C16···C21	4.30 (11)
O1···C13	2.89 (8)	C13···C21	4.31 (9)
O1···C3	2.89 (8)	N2···C9	4.31 (10)
N2···C19	2.89 (9)	C13···C16	4.32 (10)
Co···C20	2.91 (6)	C2···C14	4.32 (10)
Co···C4	2.94 (7)	C6···C12	4.33 (11)
O2···C6	2.96 (8)	C2···C11	4.34 (11)
N1···C1	2.96 (9)	C15···C21	4.34 (11)
C21···C21	3.07 (9)	C9···C22	4.35 (10)
O2···C23	3.11 (9)	O3···C1	4.35 (9)
C1···C20	3.16 (10)	O3···C13	4.35 (8)
Co···C2	3.19 (8)	C3···C11	4.36 (11)
C4···C19	3.23 (11)	N1···N2	4.36 (7)
Co···C5	3.30 (7)	N1···C9	4.36 (9)
O2···C20	3.33 (9)	C13···C13	4.36 (8)
C13···C22	3.34 (9)	C16···C22	4.37 (11)
C11···C17	3.37 (11)	C3···C18	4.38 (10)
C6···C19	3.44 (10)	C9···C17	4.38 (11)
O1···C7	3.45 (8)	C4···C7	4.38 (10)
C3···C7	3.46 (10)	C1···C8	4.40 (10)
C6···C8	3.46 (11)	Co···C3	4.40 (7)
C19···C21	3.46 (10)	C3···C17	4.41 (10)
O1···N2	3.48 (7)	Co···C6	4.41 (6)
Co···C23	3.49 (7)	C1···C22	4.42 (9)
C8···C18	3.50 (10)	C1···C17	4.42 (10)
N1···C12	3.52 (10)	C2···C15	4.43 (9)
C8···C19	3.52 (10)	C13···C16	4.43 (10)
N2···C17	3.52 (10)	C4···C12	4.44 (11)
C1···C6	3.53 (10)	C11···C21	4.44 (12)
O1···C12	3.53 (10)	Co···C12	4.48 (9)
Co···Co	3.564 (14)	Co···C8	4.56 (7)
O3···C11	3.57 (10)	Co···C18	4.67 (8)
O2···C3	3.57 (9)	Co···C1	4.68 (8)
C3···C11	3.58 (11)	Co···C17	4.70 (8)
C1···C23	3.59 (10)	Co···C13	4.70 (6)
C10···C17	3.59 (10)	Co···C4	4.76 (7)
C3···C4	3.60 (10)	Co···C2	4.82 (8)
O1—Co—N1	96 (3)	H9—C12—C2	120 (7)
O1—Co—N2	178 (2)	H9—C12—C11	118 (8)
O1—Co—O2	88 (2)	C2—C12—C11	121 (7)
O1—Co—C19	89 (2)	H10—C13—H12	108 (6)
N1—Co—N2	84 (3)	H10—C13—H11	105 (6)
N1—Co—O2	175 (2)	H10—C13—C9	112 (6)
N1—Co—C19	94 (3)	H12—C13—H11	100 (5)
N2—Co—O2	92 (2)	H12—C13—C9	126 (7)
N2—Co—C19	93 (2)	H11—C13—C9	103 (5)
O2—Co—C19	84 (3)	C15—C14—C4	122 (6)
C1—O1—Co	129 (5)	C15—C14—C18	123 (7)
C4—O2—Co	121 (4)	C4—C14—C18	114 (7)
C21—O3—C20	105 (5)	H13—C15—C14	120 (6)
C3—N1—C8	120 (6)	H13—C15—C16	120 (6)
C3—N1—Co	123 (4)	C14—C15—C16	119 (6)
C8—N1—Co	116 (5)	H14—C16—C17	123 (7)
C6—N2—C7	121 (6)	H14—C16—C15	118 (6)
C6—N2—Co	129 (5)	C17—C16—C15	119 (7)
C7—N2—Co	109 (5)	H15—C17—C16	118 (7)
O1—C1—C2	122 (7)	H15—C17—C5	118 (6)
O1—C1—C9	119 (6)	C16—C17—C5	120 (6)
C2—C1—C9	119 (7)	H17—C18—H16	114 (9)
C12—C2—C1	122 (7)	H17—C18—H18	110 (7)
C12—C2—C3	114 (6)	H17—C18—C14	113 (7)
C1—C2—C3	124 (7)	H16—C18—H18	98 (6)
H1—C3—N1	114 (6)	H16—C18—C14	106 (6)
H1—C3—C2	121 (7)	H18—C18—C14	115 (7)
N1—C3—C2	123 (6)	H19—C19—H20	121 (7)
C5—C4—O2	125 (6)	H19—C19—C20	106 (6)
C5—C4—C14	116 (7)	H19—C19—Co	108 (5)
O2—C4—C14	116 (6)	H20—C19—C20	109 (7)
C4—C5—C6	123 (7)	H20—C19—Co	103 (5)
C4—C5—C17	121 (6)	C20—C19—Co	110 (4)
C6—C5—C17	116 (6)	H21—C20—O3	105 (6)
H2—C6—N2	113 (6)	H21—C20—C23	109 (5)
H2—C6—C5	114 (6)	H21—C20—C19	113 (5)
N2—C6—C5	127 (7)	O3—C20—C23	107 (5)
H4—C7—H3	110 (7)	O3—C20—C19	109 (5)
H4—C7—C8	111 (7)	C23—C20—C19	114 (7)
H4—C7—N2	110 (6)	H22—C21—H23	102 (6)
H3—C7—C8	110 (6)	H22—C21—O3	116 (6)
H3—C7—N2	107 (6)	H22—C21—C22	110 (7)
C8—C7—N2	109 (6)	H23—C21—O3	109 (7)
H6—C8—H5	103 (6)	H23—C21—C22	104 (5)
H6—C8—C7	115 (7)	O3—C21—C22	114 (5)
H6—C8—N1	113 (6)	H24—C22—H25	103 (5)
H5—C8—C7	111 (6)	H24—C22—C21	113 (5)
H5—C8—N1	105 (6)	H24—C22—C23	112 (7)
C7—C8—N1	109 (6)	H25—C22—C21	114 (7)
C1—C9—C13	125 (7)	H25—C22—C23	115 (5)
C1—C9—C10	119 (6)	C21—C22—C23	100 (5)
C13—C9—C10	115 (6)	H26—C23—H27	110 (6)
H7—C10—C11	122 (8)	H26—C23—C20	118 (6)
H7—C10—C9	122 (7)	H26—C23—C22	112 (6)
C11—C10—C9	114 (7)	H27—C23—C20	109 (6)
H8—C11—C12	119 (8)	H27—C23—C22	103 (5)
H8—C11—C10	115 (7)	C20—C23—C22	103 (6)
C12—C11—C10	122 (8)
O2—Co—O1—C1	−174 (6)	C4—C5—C6—N2	2 (12)
N1—Co—O1—C1	8 (6)	C4—C5—C6—H2	151 (7)
N2—Co—O1—C1	−82 (66)	C17—C5—C6—N2	179 (7)
C19—Co—O1—C1	102 (6)	C17—C5—C6—H2	−32 (9)
O1—Co—O2—C4	−164 (5)	C4—C5—C17—C16	19 (10)
N1—Co—O2—C4	−7 (32)	C4—C5—C17—H15	174 (6)
N2—Co—O2—C4	18 (5)	C6—C5—C17—C16	−159 (6)
C19—Co—O2—C4	−75 (5)	C6—C5—C17—H15	−3 (*)
O1—Co—N1—C3	−19 (6)	N2—C7—C8—N1	−38 (7)
O1—Co—N1—C8	176 (4)	N2—C7—C8—H5	77 (7)
O2—Co—N1—C3	−176 (27)	N2—C7—C8—H6	−166 (5)
O2—Co—N1—C8	18 (32)	H3—C7—C8—N1	−155 (5)
N2—Co—N1—C3	159 (6)	H3—C7—C8—H5	−40 (8)
N2—Co—N1—C8	−7 (4)	H3—C7—C8—H6	77 (7)
C19—Co—N1—C3	−108 (6)	H4—C7—C8—N1	82 (7)
C19—Co—N1—C8	86 (5)	H4—C7—C8—H5	−162 (6)
O1—Co—N2—C6	−103 (64)	H4—C7—C8—H6	−46 (9)
O1—Co—N2—C7	76 (65)	C1—C9—C10—C11	−13 (10)
O2—Co—N2—C6	−12 (6)	C1—C9—C10—H7	−176 (7)
O2—Co—N2—C7	167 (4)	C13—C9—C10—C11	175 (6)
N1—Co—N2—C6	166 (6)	C13—C9—C10—H7	12 (11)
N1—Co—N2—C7	−15 (4)	C1—C9—C13—H10	−51 (*)
C19—Co—N2—C6	72 (6)	C1—C9—C13—H11	62 (9)
C19—Co—N2—C7	−108 (4)	C1—C9—C13—H12	175 (7)
O1—Co—C19—C20	0 (5)	C10—C9—C13—H10	120 (7)
O1—Co—C19—H19	115 (5)	C10—C9—C13—H11	−127 (6)
O1—Co—C19—H20	−116 (5)	C10—C9—C13—H12	−14 (10)
O2—Co—C19—C20	−88 (5)	C9—C10—C11—C12	17 (11)
O2—Co—C19—H19	26 (5)	C9—C10—C11—H8	176 (7)
O2—Co—C19—H20	156 (5)	H7—C10—C11—C12	−179 (7)
N1—Co—C19—C20	96 (5)	H7—C10—C11—H8	−21 (11)
N1—Co—C19—H19	−149 (5)	C10—C11—C12—C2	−11 (12)
N1—Co—C19—H20	−20 (5)	C10—C11—C12—H9	170 (7)
N2—Co—C19—C20	−180 (5)	H8—C11—C12—C2	−169 (8)
N2—Co—C19—H19	−65 (5)	H8—C11—C12—H9	12 (12)
N2—Co—C19—H20	64 (5)	C4—C14—C15—C16	3 (10)
Co—O1—C1—C2	−3 (11)	C4—C14—C15—H13	173 (6)
Co—O1—C1—C9	−177 (5)	C18—C14—C15—C16	−174 (6)
Co—O2—C4—C5	−19 (9)	C18—C14—C15—H13	−4 (10)
Co—O2—C4—C14	−177 (5)	C4—C14—C18—H16	−62 (8)
C21—O3—C20—C19	−146 (6)	C4—C14—C18—H17	64 (*)
C21—O3—C20—C23	−22 (8)	C4—C14—C18—H18	−169 (6)
C21—O3—C20—H21	93 (6)	C15—C14—C18—H16	115 (8)
C20—O3—C21—C22	2 (9)	C15—C14—C18—H17	−120 (9)
C20—O3—C21—H22	131 (8)	C15—C14—C18—H18	8 (*)
C20—O3—C21—H23	−114 (6)	C14—C15—C16—C17	3 (*)
Co—N1—C3—C2	24 (9)	C14—C15—C16—H14	−176 (6)
Co—N1—C3—H1	−170 (5)	H13—C15—C16—C17	−167 (6)
C8—N1—C3—C2	−170 (6)	H13—C15—C16—H14	14 (*)
C8—N1—C3—H1	−5 (9)	C15—C16—C17—C5	−14 (*)
Co—N1—C8—C7	28 (6)	C15—C16—C17—H15	−169 (6)
Co—N1—C8—H5	−92 (6)	H14—C16—C17—C5	166 (6)
Co—N1—C8—H6	157 (5)	H14—C16—C17—H15	10 (11)
C3—N1—C8—C7	−138 (6)	Co—C19—C20—O3	−163 (5)
C3—N1—C8—H5	102 (7)	Co—C19—C20—C23	78 (6)
C3—N1—C8—H6	−9 (9)	Co—C19—C20—H21	−47 (7)
Co—N2—C6—C5	4 (11)	H19—C19—C20—O3	81 (7)
Co—N2—C6—H2	−145 (5)	H19—C19—C20—C23	−38 (7)
C7—N2—C6—C5	−175 (6)	H19—C19—C20—H21	−163 (6)
C7—N2—C6—H2	35 (9)	H20—C19—C20—O3	−51 (8)
Co—N2—C7—C8	33 (6)	H20—C19—C20—C23	−170 (5)
Co—N2—C7—H3	152 (5)	H20—C19—C20—H21	65 (7)
Co—N2—C7—H4	−88 (7)	O3—C20—C23—C22	33 (7)
C6—N2—C7—C8	−147 (6)	O3—C20—C23—H26	−91 (8)
C6—N2—C7—H3	−28 (9)	O3—C20—C23—H27	142 (6)
C6—N2—C7—H4	91 (8)	C19—C20—C23—C22	153 (5)
O1—C1—C2—C3	4 (12)	C19—C20—C23—H26	29 (9)
O1—C1—C2—C12	−170 (7)	C19—C20—C23—H27	−98 (7)
C9—C1—C2—C3	179 (7)	H21—C20—C23—C22	−79 (6)
C9—C1—C2—C12	5 (12)	H21—C20—C23—H26	156 (6)
O1—C1—C9—C10	178 (7)	H21—C20—C23—H27	30 (8)
O1—C1—C9—C13	−12 (11)	O3—C21—C22—C23	18 (8)
C2—C1—C9—C10	3 (11)	O3—C21—C22—H24	136 (7)
C2—C1—C9—C13	173 (7)	O3—C21—C22—H25	−106 (7)
C1—C2—C3—N1	−16 (12)	H22—C21—C22—C23	−115 (7)
C1—C2—C3—H1	179 (7)	H22—C21—C22—H24	4 (*)
C12—C2—C3—N1	158 (7)	H22—C21—C22—H25	122 (7)
C12—C2—C3—H1	−6 (11)	H23—C21—C22—C23	137 (6)
C1—C2—C12—C11	−1 (13)	H23—C21—C22—H24	−105 (7)
C1—C2—C12—H9	178 (7)	H23—C21—C22—H25	13 (8)
C3—C2—C12—C11	−176 (7)	C21—C22—C23—C20	−30 (7)
C3—C2—C12—H9	4 (11)	C21—C22—C23—H26	99 (7)
O2—C4—C5—C6	7 (11)	C21—C22—C23—H27	−143 (6)
O2—C4—C5—C17	−170 (7)	H24—C22—C23—C20	−149 (5)
C14—C4—C5—C6	165 (7)	H24—C22—C23—H26	−21 (7)
C14—C4—C5—C17	−12 (*)	H24—C22—C23—H27	97 (6)
O2—C4—C14—C15	162 (6)	H25—C22—C23—C20	93 (6)
O2—C4—C14—C18	−21 (9)	H25—C22—C23—H26	−138 (6)
C5—C4—C14—C15	2 (10)	H25—C22—C23—H27	−20 (8)
C5—C4—C14—C18	178 (6)

 

Footnotes

¹Supplementary data for this paper are available from the IUCr electronic archives (Reference: WL2002 ). Services for accessing these data are described at the back of the journal.