{4,4′-Bis­[p-(diethyl­amino)-α-styryl]-2,2′-bi­pyridine}tri­carbonyl­chloro­rhenium(I)

In the title compound [ReCl(C₃₄H₃₈N₄)(CO)₃], the Re atom has a distorted octahedral configuration. The bi­pyridine part of the DEAS–bpy ligand and two carbonyl groups occupy the equatorial plane of the complex, with the third carbonyl ligand and the Cl atom in the axial positions. The organic ligand is essentially planar, giving rise to an extended π-conjugated system.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.065
• Data-to-parameter ratio = 25.0

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level A:



ABSTM_02  Alert A Test not performed as the _exptl_absorpt_correction_type
          has not been identified. See test ABSTY_01.

ABSTY_01  Alert A The absorption correction should be one of the following
          *  none
          *  analytical
          *  integration
          *  numerical
          *  gaussian
          *  empirical
          *  psi-scan
          *  multi-scan
          *  refdelf
          *  sphere
          *  cylinder


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           32.51
         From the CIF: _reflns_number_total              10508
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns        11793
         Completeness (_total/calc)             89.10%
          Alert B: < 90% complete (theta max?)


 Alert Level C:



PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      3
                   C3  -RE1 -N1  -C8   -134.10  0.50   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      8
                   C3  -RE1 -N1  -C4     37.80  0.60   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     12
                   C1  -RE1 -N2  -C25  -175.20  0.70   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     17
                   C1  -RE1 -N2  -C21     1.80  0.80   1.555   1.555   1.555   1.555


 2 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

S1. Comment

Re^I–polypyridine–carbonyl complexes have interesting photophysical properties (Ziessel et al., 1998); they can be used in photo- and electro-reduction reactions (Hawecker et al., 1986; O'Toole et al., 1985; Kutal et al., 1987). It has also been suggested that they may form new materials possessing non-linear optical properties (Lehn, 1987). Therefore, knowledge of the molecular and crystal structure of such complexes is essential for understanding and explaining their properties. In the present communication, we report results of an X-ray structure investigation of the title complex, (I).

The Re atom in (I) has a distorted octahedral configuration, with the bipyridine moiety of the organic ligand and two carbonyl groups in the equatorial plane, and one carbonyl ligand and a Cl atom in the axial positions (Fig. 1). The bond angle N1—Re1—N2 of 74.55 (8)° is far away from the ideal octahedral value. However, the C1—Re1—C3 angle is almost 89.4 (1)°. The axial CO ligand is displaced out of the DEAS–bpy plane [C2—Re1—N1 is 99.01 (9)°], while Cl1 is displaced towards the organic part of the molecule [N1—Re1—Cl1 is 82.94 (6)°]. Moreover, the C3 atom is considerably displaced by 0.21 Å from a plane through the other equatorial atoms. Despite the significant distortion of the Re atom configuration from octahedral, all Re—C and C—O distances are similar (Table 1), though the axial Re—C bond is somewhat shorter than the equatorial bonds. The C—O bond lengths indicate significant π-back donation from the Re atom. This can be explained by strong electron-donating properties of the organic ligand.

DEAS-bpy contains two identical parts, each consisting of the diethylaminophenyl and pyridine groups connected by an ethylene moiety. The two parts are slightly twisted with respect to each other, the dihedral angle between them being 3°. Each half of DEAS–bpy is distorted from planarity. The relevant torsion angles C23—C26—C27—C28, C24—C23—C26—C27, C26—C27—C28—C29, C6—C9—C10—C11, C5—C6—C9—C10, C9—C10—C11—C16 are 177.5 (2), -173.6 (3), -171.7 (3), 174.9 (2), -173.8 (3), and 173.4 (3)°, respectively. This non-planarity is sufficiently small to conserve the extended π-conjugated system of the organic ligand. Accordingly, the amine N3 and N4 atoms are almost coplanar with the C atoms to which they are bonded [the sums of the bond angles are 360.0 (6) and 357.6 (6)°, respectively]. Both methyl groups of each diethylamino substituent are displaced in opposite directions with respect to the mean DEAS–bpy plane.

In the crystal, molecules of (I) form dimers along the crystallographic c axis; the shortest contact in a dimer is Cl1···H5A(1 - x, 1 - y, -z) 2.65 Å.

S2. Experimental

Compound (I) was synthesized as described in the literature (Juris et al., 1988). Crystals appropriate for X-ray structure analysis were grown by diffusion of ether into a solution of compound (I) in dichloromethane.

S3. Refinement

The positions of all H atoms were found from difference Fourier syntheses. Methyl groups were refined with torsional freedom, other H atoms with a riding model. U(H) was set at 1.2 (1.5 for methyl groups) times U_eq(C). The largest positive and negative features of the final difference synthesis lie within 0.9 Å of the Re atom.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. A view of the dimer as found in the crystal. H atoms have been omitted for clarity.

{4,4'-Bis[p-(diethylamino)-alfa-styryl]-2,2' -bipyridine}chlorotricarbonylrhenium(I)

Crystal data

[ReCl(C34H38N4)(CO)3]	Dx = 1.650 Mg m^−3
Mr = 808.36	Melting point: not measured K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.4908 (5) Å	Cell parameters from 846 reflections
b = 23.1755 (5) Å	θ = 2–30°
c = 9.6971 (5) Å	µ = 3.86 mm^−1
β = 91.899 (2)°	T = 90 K
V = 3254.8 (2) Å^3	Plate, red
Z = 4	0.3 × 0.2 × 0.1 mm
F(000) = 1616

Data collection

CCD area-detector diffractometer	10508 independent reflections
Radiation source: rotating anode	8209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ϕ and ω scans	θmax = 32.5°, θmin = 1.4°
Absorption correction: (SADABS; bruker, 1998) ?	h = −21→21
Tmin = 0.391, Tmax = 0.699	k = −29→34
36470 measured reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0323P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.006
10508 reflections	Δρmax = 1.75 e Å^−3
420 parameters	Δρmin = −1.72 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00096 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement.

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

	x	y	z	Uiso*/Ueq
Re1	0.215386 (6)	0.489912 (4)	0.066402 (10)	0.01544 (4)
Cl1	0.33247 (4)	0.45493 (3)	0.24092 (6)	0.02012 (12)
O1	0.10862 (14)	0.55550 (9)	0.2851 (2)	0.0315 (5)
O2	0.06605 (13)	0.52626 (9)	−0.1454 (2)	0.0286 (4)
O3	0.09783 (12)	0.38165 (9)	0.1093 (2)	0.0258 (4)
N1	0.31880 (13)	0.55588 (9)	0.0316 (2)	0.0166 (4)
N2	0.30262 (12)	0.45487 (9)	−0.0917 (2)	0.0147 (4)
N3	0.89867 (14)	0.84891 (10)	−0.0419 (2)	0.0217 (5)
N4	0.79002 (14)	0.31395 (10)	−0.8427 (2)	0.0216 (5)
C1	0.14821 (17)	0.52952 (12)	0.2043 (3)	0.0209 (5)
C2	0.12411 (16)	0.51392 (11)	−0.0665 (3)	0.0207 (5)
C3	0.14085 (15)	0.42258 (12)	0.0944 (3)	0.0184 (5)
C4	0.38481 (15)	0.54384 (11)	−0.0610 (2)	0.0154 (5)
C5	0.45826 (16)	0.58008 (11)	−0.0814 (3)	0.0183 (5)
H5A	0.5021	0.5703	−0.1484	0.022*
C6	0.46953 (17)	0.63075 (11)	−0.0059 (3)	0.0193 (5)
C7	0.40197 (17)	0.64244 (11)	0.0904 (3)	0.0214 (5)
H7A	0.4062	0.6763	0.1456	0.026*
C8	0.32929 (17)	0.60458 (12)	0.1048 (3)	0.0209 (5)
H8A	0.2842	0.6136	0.1704	0.025*
C9	0.55102 (17)	0.66668 (12)	−0.0313 (3)	0.0217 (5)
H9A	0.5885	0.6552	−0.1050	0.026*
C10	0.57749 (17)	0.71350 (12)	0.0384 (3)	0.0220 (5)
H10A	0.5375	0.7270	0.1071	0.026*
C11	0.66233 (16)	0.74634 (12)	0.0194 (3)	0.0213 (5)
C12	0.73239 (17)	0.72844 (12)	−0.0680 (3)	0.0220 (5)
H12A	0.7259	0.6926	−0.1147	0.026*
C13	0.81064 (17)	0.76139 (12)	−0.0882 (3)	0.0219 (5)
H13A	0.8563	0.7478	−0.1484	0.026*
C14	0.82320 (16)	0.81477 (11)	−0.0207 (3)	0.0186 (5)
C15	0.75400 (17)	0.83178 (12)	0.0707 (3)	0.0211 (5)
H15A	0.7605	0.8671	0.1198	0.025*
C16	0.67758 (17)	0.79797 (12)	0.0893 (3)	0.0215 (5)
H16A	0.6332	0.8104	0.1527	0.026*
C17	0.97011 (17)	0.83081 (13)	−0.1354 (3)	0.0241 (6)
H17A	0.9815	0.7890	−0.1221	0.029*
H17B	1.0281	0.8513	−0.1097	0.029*
C18	0.94727 (19)	0.84179 (14)	−0.2881 (3)	0.0296 (6)
H18A	1.0023	0.8349	−0.3418	0.044*
H18B	0.9271	0.8819	−0.3007	0.044*
H18C	0.8977	0.8157	−0.3197	0.044*
C19	0.90892 (18)	0.90586 (12)	0.0221 (3)	0.0263 (6)
H19A	0.9753	0.9160	0.0277	0.032*
H19B	0.8869	0.9038	0.1175	0.032*
C20	0.8571 (2)	0.95339 (14)	−0.0537 (3)	0.0367 (7)
H20A	0.8712	0.9905	−0.0094	0.055*
H20B	0.7906	0.9460	−0.0511	0.055*
H20C	0.8759	0.9545	−0.1498	0.055*
C21	0.37290 (15)	0.48832 (11)	−0.1345 (3)	0.0151 (4)
C22	0.43071 (15)	0.47071 (11)	−0.2385 (3)	0.0174 (5)
H22A	0.4795	0.4951	−0.2656	0.021*
C23	0.41739 (15)	0.41755 (11)	−0.3029 (3)	0.0172 (5)
C24	0.34359 (16)	0.38404 (12)	−0.2582 (3)	0.0186 (5)
H24A	0.3308	0.3477	−0.3000	0.022*
C25	0.28946 (15)	0.40378 (11)	−0.1536 (3)	0.0174 (5)
H25A	0.2405	0.3800	−0.1242	0.021*
C26	0.47621 (16)	0.39445 (12)	−0.4085 (3)	0.0203 (5)
H26A	0.4575	0.3589	−0.4493	0.024*
C27	0.55387 (16)	0.41793 (11)	−0.4544 (3)	0.0180 (5)
H27A	0.5722	0.4543	−0.4175	0.022*
C28	0.61233 (15)	0.39184 (11)	−0.5570 (3)	0.0173 (5)
C29	0.69850 (16)	0.41584 (11)	−0.5858 (3)	0.0198 (5)
H29A	0.7169	0.4507	−0.5411	0.024*
C30	0.75763 (17)	0.39031 (12)	−0.6774 (3)	0.0209 (5)
H30A	0.8159	0.4076	−0.6928	0.025*
C31	0.73285 (16)	0.33942 (11)	−0.7478 (3)	0.0191 (5)
C32	0.64613 (16)	0.31511 (12)	−0.7202 (3)	0.0197 (5)
H32A	0.6269	0.2807	−0.7661	0.024*
C33	0.58881 (16)	0.34088 (11)	−0.6268 (3)	0.0198 (5)
H33A	0.5312	0.3232	−0.6094	0.024*
C34	0.76058 (19)	0.26263 (13)	−0.9191 (3)	0.0244 (6)
H34A	0.7958	0.2604	−1.0047	0.029*
H34B	0.6945	0.2669	−0.9464	0.029*
C35	0.77303 (18)	0.20632 (12)	−0.8410 (3)	0.0251 (6)
H35A	0.7485	0.1745	−0.8977	0.038*
H35B	0.7398	0.2082	−0.7547	0.038*
H35C	0.8389	0.1998	−0.8202	0.038*
C36	0.88844 (18)	0.32694 (13)	−0.8383 (3)	0.0269 (6)
H36A	0.8967	0.3692	−0.8472	0.032*
H36B	0.9171	0.3085	−0.9183	0.032*
C37	0.93833 (18)	0.30672 (14)	−0.7073 (3)	0.0291 (6)
H37A	1.0040	0.3163	−0.7113	0.044*
H37B	0.9313	0.2649	−0.6982	0.044*
H37C	0.9120	0.3259	−0.6276	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01416 (5)	0.01235 (6)	0.02007 (6)	0.00031 (3)	0.00446 (3)	−0.00081 (4)
Cl1	0.0184 (2)	0.0192 (3)	0.0228 (3)	−0.0010 (2)	0.0022 (2)	0.0026 (2)
O1	0.0346 (10)	0.0269 (12)	0.0337 (12)	0.0069 (9)	0.0137 (9)	−0.0057 (9)
O2	0.0209 (8)	0.0270 (11)	0.0379 (12)	0.0023 (8)	−0.0002 (8)	0.0044 (9)
O3	0.0261 (9)	0.0206 (11)	0.0311 (11)	−0.0063 (8)	0.0086 (8)	−0.0018 (8)
N1	0.0185 (9)	0.0118 (11)	0.0194 (11)	−0.0001 (7)	0.0013 (8)	0.0002 (8)
N2	0.0144 (8)	0.0109 (11)	0.0190 (10)	−0.0003 (7)	0.0008 (7)	0.0024 (8)
N3	0.0192 (9)	0.0182 (12)	0.0280 (12)	−0.0026 (8)	0.0042 (8)	−0.0018 (9)
N4	0.0230 (10)	0.0171 (12)	0.0251 (12)	0.0019 (8)	0.0063 (9)	−0.0007 (9)
C1	0.0221 (10)	0.0153 (12)	0.0257 (13)	0.0017 (10)	0.0049 (9)	0.0043 (11)
C2	0.0171 (10)	0.0143 (13)	0.0311 (14)	−0.0010 (9)	0.0055 (9)	−0.0022 (11)
C3	0.0143 (9)	0.0220 (14)	0.0191 (12)	0.0013 (9)	0.0042 (8)	−0.0032 (10)
C4	0.0162 (9)	0.0141 (13)	0.0161 (11)	0.0021 (8)	0.0003 (8)	0.0030 (9)
C5	0.0180 (10)	0.0163 (13)	0.0207 (13)	0.0003 (9)	0.0003 (9)	0.0027 (10)
C6	0.0197 (10)	0.0157 (13)	0.0222 (13)	−0.0014 (9)	−0.0046 (9)	0.0045 (10)
C7	0.0276 (12)	0.0131 (13)	0.0234 (14)	0.0006 (10)	0.0005 (10)	0.0001 (10)
C8	0.0221 (11)	0.0175 (14)	0.0233 (14)	0.0022 (9)	0.0037 (10)	−0.0012 (10)
C9	0.0215 (11)	0.0193 (14)	0.0245 (14)	0.0010 (10)	0.0015 (10)	0.0008 (10)
C10	0.0212 (11)	0.0199 (14)	0.0251 (14)	0.0028 (9)	0.0018 (10)	0.0026 (10)
C11	0.0186 (10)	0.0232 (15)	0.0220 (13)	−0.0003 (9)	−0.0010 (9)	0.0070 (10)
C12	0.0270 (12)	0.0155 (14)	0.0234 (14)	−0.0012 (10)	−0.0029 (10)	−0.0002 (10)
C13	0.0227 (11)	0.0175 (14)	0.0258 (14)	0.0015 (10)	0.0036 (10)	−0.0006 (10)
C14	0.0174 (10)	0.0170 (13)	0.0213 (13)	0.0002 (9)	0.0001 (9)	0.0016 (10)
C15	0.0231 (11)	0.0189 (14)	0.0213 (13)	0.0007 (10)	0.0015 (9)	−0.0011 (10)
C16	0.0210 (11)	0.0231 (15)	0.0204 (13)	0.0029 (10)	0.0020 (9)	0.0022 (10)
C17	0.0211 (11)	0.0236 (15)	0.0277 (15)	−0.0009 (10)	0.0037 (10)	0.0021 (11)
C18	0.0278 (13)	0.0344 (18)	0.0268 (15)	0.0055 (12)	0.0033 (11)	0.0010 (12)
C19	0.0280 (13)	0.0195 (15)	0.0313 (15)	−0.0048 (11)	−0.0002 (11)	−0.0012 (11)
C20	0.0554 (19)	0.0207 (17)	0.0335 (17)	0.0014 (14)	−0.0057 (15)	−0.0021 (13)
C21	0.0139 (9)	0.0150 (12)	0.0165 (12)	0.0008 (8)	0.0000 (8)	0.0012 (9)
C22	0.0160 (9)	0.0151 (12)	0.0214 (12)	0.0004 (9)	0.0025 (9)	0.0016 (10)
C23	0.0158 (10)	0.0183 (13)	0.0175 (12)	0.0021 (9)	0.0012 (8)	0.0003 (9)
C24	0.0195 (10)	0.0145 (13)	0.0219 (13)	−0.0012 (9)	−0.0001 (9)	−0.0004 (10)
C25	0.0164 (10)	0.0153 (13)	0.0206 (12)	−0.0010 (9)	0.0012 (9)	0.0002 (9)
C26	0.0201 (11)	0.0195 (14)	0.0215 (13)	−0.0005 (9)	0.0017 (9)	−0.0046 (10)
C27	0.0205 (10)	0.0143 (13)	0.0191 (12)	0.0010 (9)	0.0005 (9)	−0.0023 (9)
C28	0.0182 (10)	0.0150 (13)	0.0186 (12)	0.0022 (9)	0.0014 (9)	0.0026 (9)
C29	0.0232 (11)	0.0137 (13)	0.0225 (13)	−0.0007 (9)	0.0033 (9)	−0.0004 (10)
C30	0.0210 (11)	0.0165 (14)	0.0254 (14)	−0.0023 (9)	0.0067 (10)	0.0033 (10)
C31	0.0218 (11)	0.0168 (14)	0.0190 (12)	0.0039 (9)	0.0038 (9)	0.0033 (10)
C32	0.0205 (11)	0.0168 (14)	0.0217 (13)	0.0015 (9)	−0.0004 (9)	−0.0001 (10)
C33	0.0159 (10)	0.0190 (14)	0.0246 (13)	0.0007 (9)	0.0010 (9)	−0.0013 (10)
C34	0.0304 (13)	0.0263 (16)	0.0168 (13)	0.0043 (11)	0.0025 (10)	−0.0030 (11)
C35	0.0259 (12)	0.0203 (15)	0.0292 (15)	0.0014 (10)	0.0006 (11)	−0.0019 (11)
C36	0.0284 (13)	0.0202 (15)	0.0328 (16)	−0.0009 (11)	0.0131 (11)	−0.0005 (11)
C37	0.0241 (12)	0.0294 (17)	0.0337 (16)	−0.0025 (11)	0.0012 (11)	−0.0045 (12)

Geometric parameters (Å, º)

Re1—C2	1.899 (3)	C9—C10	1.328 (4)
Re1—C1	1.914 (3)	C10—C11	1.463 (3)
Re1—C3	1.922 (3)	C11—C16	1.389 (4)
Re1—N1	2.175 (2)	C11—C12	1.406 (4)
Re1—N2	2.176 (2)	C12—C13	1.387 (4)
Re1—Cl1	2.4919 (6)	C13—C14	1.409 (4)
O1—C1	1.156 (3)	C14—C15	1.416 (3)
O2—C2	1.155 (3)	C15—C16	1.373 (4)
O3—C3	1.147 (3)	C17—C18	1.528 (4)
N1—C8	1.340 (3)	C19—C20	1.510 (4)
N1—C4	1.362 (3)	C21—C22	1.393 (3)
N2—C25	1.338 (3)	C22—C23	1.392 (4)
N2—C21	1.356 (3)	C23—C24	1.402 (3)
N3—C14	1.371 (3)	C23—C26	1.456 (3)
N3—C17	1.460 (3)	C24—C25	1.381 (3)
N3—C19	1.464 (4)	C26—C27	1.339 (3)
N4—C31	1.390 (3)	C27—C28	1.459 (3)
N4—C36	1.457 (3)	C28—C33	1.398 (4)
N4—C34	1.457 (4)	C28—C29	1.403 (3)
C4—C5	1.375 (3)	C29—C30	1.387 (3)
C4—C21	1.478 (4)	C30—C31	1.403 (4)
C5—C6	1.391 (4)	C31—C32	1.411 (3)
C6—C7	1.402 (4)	C32—C33	1.384 (3)
C6—C9	1.472 (4)	C34—C35	1.517 (4)
C7—C8	1.381 (4)	C36—C37	1.515 (4)
C2—Re1—C1	88.54 (11)	N1—C8—C7	123.7 (2)
C2—Re1—C3	87.22 (11)	C10—C9—C6	126.7 (3)
C1—Re1—C3	89.41 (11)	C9—C10—C11	126.2 (3)
C2—Re1—N1	99.01 (9)	C16—C11—C12	116.2 (2)
C1—Re1—N1	98.07 (10)	C16—C11—C10	120.5 (2)
C3—Re1—N1	170.35 (9)	C12—C11—C10	123.3 (3)
C2—Re1—N2	92.24 (9)	C13—C12—C11	122.2 (3)
C1—Re1—N2	172.61 (10)	C12—C13—C14	120.8 (2)
C3—Re1—N2	97.97 (9)	N3—C14—C13	121.9 (2)
N1—Re1—N2	74.55 (8)	N3—C14—C15	121.2 (2)
C2—Re1—Cl1	177.94 (8)	C13—C14—C15	116.9 (2)
C1—Re1—Cl1	91.85 (8)	C16—C15—C14	120.9 (3)
C3—Re1—Cl1	90.76 (8)	C15—C16—C11	122.9 (2)
N1—Re1—Cl1	82.94 (6)	N3—C17—C18	114.7 (2)
N2—Re1—Cl1	87.63 (5)	N3—C19—C20	114.2 (2)
C8—N1—C4	116.9 (2)	N2—C21—C22	122.0 (2)
C8—N1—Re1	125.21 (16)	N2—C21—C4	115.3 (2)
C4—N1—Re1	117.44 (16)	C22—C21—C4	122.7 (2)
C25—N2—C21	117.7 (2)	C23—C22—C21	120.4 (2)
C25—N2—Re1	124.67 (15)	C22—C23—C24	116.6 (2)
C21—N2—Re1	117.52 (16)	C22—C23—C26	124.4 (2)
C14—N3—C17	120.9 (2)	C24—C23—C26	119.0 (2)
C14—N3—C19	121.8 (2)	C25—C24—C23	120.1 (2)
C17—N3—C19	117.3 (2)	N2—C25—C24	123.2 (2)
C31—N4—C36	119.8 (2)	C27—C26—C23	127.0 (2)
C31—N4—C34	120.8 (2)	C26—C27—C28	124.9 (2)
C36—N4—C34	117.0 (2)	C33—C28—C29	116.3 (2)
O1—C1—Re1	177.3 (2)	C33—C28—C27	122.9 (2)
O2—C2—Re1	176.7 (2)	C29—C28—C27	120.8 (2)
O3—C3—Re1	178.4 (2)	C30—C29—C28	122.1 (2)
N1—C4—C5	122.3 (2)	C29—C30—C31	121.1 (2)
N1—C4—C21	115.0 (2)	N4—C31—C30	122.0 (2)
C5—C4—C21	122.7 (2)	N4—C31—C32	120.7 (2)
C4—C5—C6	121.2 (2)	C30—C31—C32	117.3 (2)
C5—C6—C7	116.2 (2)	C33—C32—C31	120.6 (2)
C5—C6—C9	118.1 (2)	C32—C33—C28	122.6 (2)
C7—C6—C9	125.7 (2)	N4—C34—C35	114.9 (2)
C8—C7—C6	119.7 (2)	N4—C36—C37	113.6 (2)
C2—Re1—N1—C8	96.2 (2)	C13—C14—C15—C16	−1.4 (4)
C1—Re1—N1—C8	6.4 (2)	C14—C15—C16—C11	−1.2 (4)
C3—Re1—N1—C8	−134.1 (5)	C12—C11—C16—C15	3.1 (4)
N2—Re1—N1—C8	−174.0 (2)	C10—C11—C16—C15	−177.0 (2)
Cl1—Re1—N1—C8	−84.5 (2)	C14—N3—C17—C18	81.1 (3)
C2—Re1—N1—C4	−91.92 (18)	C19—N3—C17—C18	−96.0 (3)
C1—Re1—N1—C4	178.29 (18)	C14—N3—C19—C20	−82.0 (3)
C3—Re1—N1—C4	37.8 (6)	C17—N3—C19—C20	95.0 (3)
N2—Re1—N1—C4	−2.08 (17)	C25—N2—C21—C22	−0.5 (3)
Cl1—Re1—N1—C4	87.41 (17)	Re1—N2—C21—C22	−177.77 (18)
C2—Re1—N2—C25	−79.3 (2)	C25—N2—C21—C4	−179.2 (2)
C1—Re1—N2—C25	−175.2 (7)	Re1—N2—C21—C4	3.6 (3)
C3—Re1—N2—C25	8.2 (2)	N1—C4—C21—N2	−5.3 (3)
N1—Re1—N2—C25	−178.0 (2)	C5—C4—C21—N2	173.1 (2)
Cl1—Re1—N2—C25	98.68 (19)	N1—C4—C21—C22	176.1 (2)
C2—Re1—N2—C21	97.77 (18)	C5—C4—C21—C22	−5.6 (4)
C1—Re1—N2—C21	1.8 (8)	N2—C21—C22—C23	0.4 (4)
C3—Re1—N2—C21	−174.72 (18)	C4—C21—C22—C23	178.9 (2)
N1—Re1—N2—C21	−0.96 (16)	C21—C22—C23—C24	0.4 (4)
Cl1—Re1—N2—C21	−84.28 (16)	C21—C22—C23—C26	−177.5 (2)
C8—N1—C4—C5	−1.2 (3)	C22—C23—C24—C25	−1.1 (4)
Re1—N1—C4—C5	−173.82 (18)	C26—C23—C24—C25	176.9 (2)
C8—N1—C4—C21	177.1 (2)	C21—N2—C25—C24	−0.2 (4)
Re1—N1—C4—C21	4.6 (3)	Re1—N2—C25—C24	176.83 (18)
N1—C4—C5—C6	1.2 (4)	C23—C24—C25—N2	1.0 (4)
C21—C4—C5—C6	−177.0 (2)	C22—C23—C26—C27	4.2 (4)
C4—C5—C6—C7	−0.3 (4)	C24—C23—C26—C27	−173.6 (3)
C4—C5—C6—C9	178.6 (2)	C23—C26—C27—C28	177.5 (2)
C5—C6—C7—C8	−0.5 (4)	C26—C27—C28—C33	5.3 (4)
C9—C6—C7—C8	−179.3 (2)	C26—C27—C28—C29	−171.7 (3)
C4—N1—C8—C7	0.4 (4)	C33—C28—C29—C30	−0.5 (4)
Re1—N1—C8—C7	172.38 (19)	C27—C28—C29—C30	176.6 (2)
C6—C7—C8—N1	0.4 (4)	C28—C29—C30—C31	1.1 (4)
C5—C6—C9—C10	−173.8 (3)	C36—N4—C31—C30	21.1 (4)
C7—C6—C9—C10	5.0 (4)	C34—N4—C31—C30	−177.1 (2)
C6—C9—C10—C11	174.9 (2)	C36—N4—C31—C32	−159.8 (2)
C9—C10—C11—C16	173.4 (3)	C34—N4—C31—C32	2.0 (4)
C9—C10—C11—C12	−6.7 (4)	C29—C30—C31—N4	178.3 (2)
C16—C11—C12—C13	−2.6 (4)	C29—C30—C31—C32	−0.7 (4)
C10—C11—C12—C13	177.5 (2)	N4—C31—C32—C33	−179.3 (2)
C11—C12—C13—C14	0.2 (4)	C30—C31—C32—C33	−0.2 (4)
C17—N3—C14—C13	−0.6 (4)	C31—C32—C33—C28	0.8 (4)
C19—N3—C14—C13	176.4 (2)	C29—C28—C33—C32	−0.5 (4)
C17—N3—C14—C15	179.4 (2)	C27—C28—C33—C32	−177.5 (2)
C19—N3—C14—C15	−3.6 (4)	C31—N4—C34—C35	−81.4 (3)
C12—C13—C14—N3	−178.1 (2)	C36—N4—C34—C35	80.9 (3)
C12—C13—C14—C15	1.8 (4)	C31—N4—C36—C37	64.3 (3)
N3—C14—C15—C16	178.6 (2)	C34—N4—C36—C37	−98.2 (3)