Silver(I) and rhenium(I) metal complexes of a 2,2'-bi­pyridine-functionalized third-generation tris­(pyrazol­yl)methane ligand

Heterotopic ligands offer the possibility of preparing polynuclear bimetallic complexes. Recent studies of heteroditopic ligands and their metal complexes have focused on novel supra­molecular systems, biological activity, and the development of MRI contrast agents. The heteroditopic ligand Bipy-CH₂-O-CH₂-C(pz)₃ (Bipy-L; Bipy is 2,2'-bi­pyridine and pz is pyrazol­yl) reacts with AgBF₄ to produce the coordination polymer catena-poly[[silver(I)-([mu]-5-{[tris­(pyrazol-1-yl)meth­oxy]methyl-[kappa]²N,N'}-2,2'-bi­pyri­­dine-[kappa]²N,N')] diethyl ether hemisolvate], {[Ag(C₂₂H₂₀N₈O)]BF₄·0.5C₄H₁₀O}_n, and with Re(CO)₅Br to form the discrete compound bromido­tricarbon­yl(5-{[tris­(pyrazol-1-yl)meth­oxy]meth­yl}-2,2'-bi­pyridine-[kappa]²N,N')rhenium(I), [ReBr(C₂₂H₂₀N₈O)(CO)₃]. The silver(I) com­pound is a one-dimensional coordination polymer, built up by a [kappa]² coordination mode of the bi­pyridine group and a [kappa]²-[kappa]⁰ coordination mode of the -C(pz)₃ donor set. In [ReBr(Bipy-L)(CO)₃], the ligand coordinates only via the bi­pyridine end, leaving the -C(pz)₃ donor set free for further coordination interactions.

Computing details

Data collection: SMART-NT (Bruker, 2000) for ag; SMART (Bruker, 2000) for re. For both compounds, cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL214 (Sheldrick, 2015b); molecular graphics: various; software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(ag) catena-Poly[[silver(I)-(µ-5-{[tris(pyrazol-1-yl)methoxy]methyl-κ²N,N'}-2,2'-bipyridine-κ²N,N')] diethyl ether hemisolvate]

Crystal data

[Ag(C22H20N8O)]BF4·0.5C4H10O	F(000) = 2600
Mr = 644.20	Dx = 1.627 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.4544 (6) Å	Cell parameters from 7479 reflections
b = 11.9881 (4) Å	θ = 2.2–25.5°
c = 21.4952 (7) Å	µ = 0.83 mm^−1
β = 93.493 (1)°	T = 150 K
V = 5261.0 (3) Å^3	Plate, colourless
Z = 8	0.22 × 0.2 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer	5386 independent reflections
Radiation source: fine-focus sealed tube	4393 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 10.2 pixels mm^-1	θmax = 26.4°, θmin = 1.9°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −14→14
Tmin = 0.809, Tmax = 0.862	l = −26→26
29051 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 8.8517P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
5386 reflections	Δρmax = 1.48 e Å^−3
368 parameters	Δρmin = −0.42 e Å^−3
17 restraints

Special details

Experimental. Absorption correction: SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0572 before and 0.0514 after correction. The Ratio of minimum to maximum transmission is 0.9389. The λ/2 correction factor is Not present.

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.39089 (2)	−0.03640 (2)	0.56094 (2)	0.04528 (13)
C1	0.41769 (15)	0.2360 (3)	0.61004 (14)	0.0292 (7)
C2	0.42945 (17)	0.3551 (3)	0.63416 (16)	0.0347 (7)
H2A	0.3885	0.3990	0.6293	0.042*
H2B	0.4443	0.3537	0.6789	0.042*
C3	0.48622 (19)	0.5198 (3)	0.61131 (19)	0.0418 (8)
H3A	0.5319	0.5418	0.6045	0.050*
H3B	0.4783	0.5342	0.6556	0.050*
C11	0.53455 (16)	0.1976 (3)	0.64932 (16)	0.0364 (7)
H11	0.5438	0.2652	0.6712	0.044*
C12	0.57549 (18)	0.1093 (3)	0.6449 (2)	0.0465 (9)
H12	0.6187	0.1020	0.6632	0.056*
C13	0.54083 (19)	0.0317 (3)	0.6078 (2)	0.0473 (9)
H13	0.5578	−0.0385	0.5961	0.057*
C21	0.3336 (2)	0.2282 (4)	0.69197 (19)	0.0535 (11)
H21	0.3417	0.2979	0.7119	0.064*
C22	0.2872 (2)	0.1535 (4)	0.7055 (2)	0.0638 (13)
H22	0.2566	0.1596	0.7369	0.077*
C23	0.2936 (2)	0.0664 (4)	0.6642 (2)	0.0520 (10)
H23	0.2668	0.0015	0.6628	0.062*
C31	0.43273 (18)	0.2356 (3)	0.49388 (15)	0.0356 (7)
H31	0.4776	0.2154	0.4935	0.043*
C32	0.3923 (2)	0.2664 (3)	0.44409 (17)	0.0442 (9)
H32	0.4030	0.2706	0.4017	0.053*
C33	0.3323 (2)	0.2905 (3)	0.46813 (19)	0.0485 (10)
H33	0.2947	0.3143	0.4436	0.058*
C41	0.42845 (17)	0.7005 (3)	0.58584 (16)	0.0361 (7)
H41	0.4484	0.7282	0.6238	0.043*
C42	0.43987 (17)	0.5899 (3)	0.57030 (16)	0.0353 (7)
C43	0.4101 (2)	0.5516 (3)	0.51489 (18)	0.0434 (9)
H43	0.4166	0.4768	0.5022	0.052*
C44	0.37070 (19)	0.6221 (3)	0.47798 (17)	0.0414 (8)
H44	0.3504	0.5962	0.4398	0.050*
C45	0.36118 (16)	0.7314 (3)	0.49737 (15)	0.0331 (7)
C46	0.31832 (17)	0.8106 (3)	0.46019 (16)	0.0361 (7)
C47	0.27481 (18)	0.7750 (3)	0.41197 (17)	0.0432 (9)
H47	0.2706	0.6979	0.4025	0.052*
C48	0.2378 (2)	0.8530 (4)	0.37795 (18)	0.0503 (10)
H48	0.2086	0.8300	0.3443	0.060*
C49	0.2436 (2)	0.9643 (4)	0.3934 (2)	0.0554 (11)
H49	0.2189	1.0197	0.3707	0.067*
C50	0.2864 (2)	0.9924 (4)	0.4427 (2)	0.0519 (10)
H50	0.2896	1.0688	0.4542	0.062*
N11	0.48115 (14)	0.0677 (2)	0.59070 (14)	0.0356 (6)
N12	0.47787 (13)	0.1714 (2)	0.61659 (12)	0.0308 (6)
N21	0.34115 (16)	0.0844 (3)	0.62706 (15)	0.0445 (7)
N22	0.36634 (14)	0.1850 (2)	0.64452 (13)	0.0337 (6)
N31	0.33409 (15)	0.2763 (3)	0.52960 (15)	0.0433 (7)
N32	0.39559 (13)	0.2397 (2)	0.54416 (12)	0.0317 (6)
N41	0.39109 (13)	0.7702 (2)	0.55054 (13)	0.0338 (6)
N42	0.32355 (15)	0.9192 (3)	0.47544 (14)	0.0408 (7)
O1	0.47821 (12)	0.40332 (19)	0.59864 (11)	0.0380 (6)
B1A	0.3660 (3)	0.4799 (5)	0.7889 (3)	0.0502 (8)	0.832 (8)
F1A	0.4261 (2)	0.4321 (4)	0.7813 (2)	0.0502 (8)	0.832 (8)
F2A	0.3684 (2)	0.5634 (5)	0.8318 (2)	0.0874 (17)	0.832 (8)
F3A	0.3379 (2)	0.5114 (4)	0.73302 (15)	0.0782 (17)	0.832 (8)
F4A	0.3253 (2)	0.3949 (4)	0.8100 (2)	0.0982 (18)	0.832 (8)
B1B	0.3673 (10)	0.4830 (18)	0.7796 (10)	0.0502 (8)	0.168 (8)
F1B	0.4177 (11)	0.408 (2)	0.7747 (14)	0.0502 (8)	0.168 (8)
F2B	0.3620 (14)	0.513 (2)	0.8394 (10)	0.0874 (17)	0.168 (8)
F3B	0.3761 (13)	0.5661 (19)	0.7380 (11)	0.097 (8)*	0.168 (8)
F4B	0.3058 (8)	0.4369 (16)	0.7629 (9)	0.067 (6)*	0.168 (8)
C1S	0.3593 (10)	0.845 (3)	0.7681 (13)	0.209 (12)*	0.5
H1SA	0.3601	0.7656	0.7783	0.314*	0.5
H1SB	0.3234	0.8601	0.7369	0.314*	0.5
H1SC	0.3528	0.8887	0.8058	0.314*	0.5
C2S	0.4230 (8)	0.878 (2)	0.7423 (10)	0.144 (7)*	0.5
H2SA	0.4227	0.8492	0.6990	0.173*	0.5
H2SB	0.4241	0.9600	0.7399	0.173*	0.5
O1S	0.4823 (7)	0.8421 (13)	0.7738 (7)	0.171 (6)*	0.5
C3S	0.5425 (8)	0.8901 (18)	0.7671 (13)	0.174 (10)*	0.5
H3SA	0.5525	0.9329	0.8059	0.209*	0.5
H3SB	0.5355	0.9460	0.7334	0.209*	0.5
C4S	0.6044 (8)	0.8312 (17)	0.7540 (9)	0.126 (6)*	0.5
H4SA	0.6376	0.8462	0.7877	0.188*	0.5
H4SB	0.6199	0.8580	0.7144	0.188*	0.5
H4SC	0.5962	0.7508	0.7512	0.188*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0546 (2)	0.02839 (18)	0.0519 (2)	−0.00235 (12)	−0.00517 (14)	−0.00991 (12)
C1	0.0318 (16)	0.0275 (16)	0.0285 (15)	−0.0001 (13)	0.0032 (12)	0.0009 (12)
C2	0.0409 (18)	0.0257 (17)	0.0377 (18)	0.0008 (14)	0.0047 (14)	−0.0028 (13)
C3	0.046 (2)	0.0279 (19)	0.050 (2)	−0.0023 (15)	−0.0062 (17)	0.0019 (15)
C11	0.0366 (18)	0.0335 (18)	0.0383 (18)	−0.0036 (14)	−0.0033 (14)	0.0015 (14)
C12	0.0350 (19)	0.043 (2)	0.061 (2)	−0.0001 (16)	−0.0070 (17)	0.0026 (18)
C13	0.040 (2)	0.036 (2)	0.065 (3)	0.0093 (16)	0.0014 (18)	−0.0002 (17)
C21	0.060 (2)	0.058 (3)	0.045 (2)	−0.012 (2)	0.0218 (19)	−0.0160 (19)
C22	0.065 (3)	0.074 (3)	0.055 (3)	−0.019 (2)	0.027 (2)	−0.012 (2)
C23	0.050 (2)	0.047 (2)	0.060 (3)	−0.0143 (19)	0.0153 (19)	−0.0029 (19)
C31	0.0425 (18)	0.0305 (18)	0.0337 (17)	−0.0050 (14)	0.0021 (14)	−0.0006 (14)
C32	0.069 (3)	0.0321 (19)	0.0310 (18)	−0.0064 (18)	−0.0007 (17)	−0.0004 (14)
C33	0.057 (2)	0.036 (2)	0.050 (2)	−0.0003 (18)	−0.0179 (19)	0.0062 (17)
C41	0.0376 (18)	0.0328 (18)	0.0377 (18)	−0.0053 (14)	−0.0002 (14)	−0.0023 (14)
C42	0.0363 (17)	0.0271 (17)	0.0423 (19)	−0.0064 (14)	0.0007 (14)	0.0022 (14)
C43	0.057 (2)	0.0264 (18)	0.046 (2)	−0.0020 (16)	−0.0021 (17)	−0.0045 (15)
C44	0.054 (2)	0.0347 (19)	0.0342 (18)	−0.0030 (16)	−0.0052 (16)	−0.0049 (15)
C45	0.0351 (17)	0.0309 (18)	0.0337 (17)	−0.0035 (14)	0.0039 (13)	0.0011 (13)
C46	0.0357 (17)	0.0388 (19)	0.0340 (17)	−0.0004 (15)	0.0039 (14)	0.0027 (14)
C47	0.0422 (19)	0.044 (2)	0.043 (2)	−0.0076 (17)	0.0003 (16)	−0.0017 (16)
C48	0.042 (2)	0.071 (3)	0.038 (2)	−0.0005 (19)	−0.0038 (16)	0.0054 (19)
C49	0.048 (2)	0.063 (3)	0.054 (3)	0.014 (2)	−0.0040 (19)	0.011 (2)
C50	0.057 (2)	0.041 (2)	0.058 (3)	0.0086 (19)	0.000 (2)	0.0033 (19)
N11	0.0375 (15)	0.0242 (14)	0.0448 (16)	0.0011 (12)	0.0004 (12)	−0.0037 (12)
N12	0.0340 (14)	0.0253 (14)	0.0328 (14)	0.0003 (11)	0.0004 (11)	−0.0013 (11)
N21	0.0449 (17)	0.0360 (17)	0.0536 (19)	−0.0105 (14)	0.0118 (15)	−0.0072 (14)
N22	0.0368 (15)	0.0306 (15)	0.0342 (14)	−0.0022 (12)	0.0057 (12)	−0.0031 (12)
N31	0.0360 (15)	0.0437 (18)	0.0491 (18)	0.0075 (14)	−0.0067 (13)	0.0031 (14)
N32	0.0350 (14)	0.0292 (15)	0.0306 (14)	0.0026 (11)	0.0005 (11)	−0.0001 (11)
N41	0.0352 (14)	0.0293 (15)	0.0370 (15)	−0.0024 (12)	0.0028 (12)	−0.0018 (11)
N42	0.0414 (16)	0.0347 (16)	0.0457 (17)	0.0042 (13)	−0.0016 (13)	0.0017 (13)
O1	0.0442 (14)	0.0246 (12)	0.0453 (14)	−0.0018 (10)	0.0026 (11)	0.0007 (10)
B1A	0.0565 (15)	0.052 (2)	0.0412 (16)	0.0194 (14)	−0.0071 (11)	−0.0142 (14)
F1A	0.0565 (15)	0.052 (2)	0.0412 (16)	0.0194 (14)	−0.0071 (11)	−0.0142 (14)
F2A	0.080 (2)	0.081 (3)	0.096 (3)	0.041 (3)	−0.0330 (19)	−0.065 (3)
F3A	0.095 (3)	0.091 (3)	0.0456 (18)	0.048 (3)	−0.0247 (18)	−0.0032 (18)
F4A	0.100 (3)	0.077 (3)	0.123 (4)	0.005 (2)	0.057 (3)	0.007 (3)
B1B	0.0565 (15)	0.052 (2)	0.0412 (16)	0.0194 (14)	−0.0071 (11)	−0.0142 (14)
F1B	0.0565 (15)	0.052 (2)	0.0412 (16)	0.0194 (14)	−0.0071 (11)	−0.0142 (14)
F2B	0.080 (2)	0.081 (3)	0.096 (3)	0.041 (3)	−0.0330 (19)	−0.065 (3)

Geometric parameters (Å, º)

Ag1—N11	2.287 (3)	C44—H44	0.9500
Ag1—N21	2.308 (3)	C44—C45	1.392 (5)
Ag1—N41^i	2.329 (3)	C45—C46	1.491 (5)
Ag1—N42^i	2.291 (3)	C45—N41	1.346 (4)
C1—C2	1.532 (5)	C46—C47	1.391 (5)
C1—N12	1.454 (4)	C46—N42	1.346 (5)
C1—N22	1.456 (4)	C47—H47	0.9500
C1—N32	1.461 (4)	C47—C48	1.384 (6)
C2—H2A	0.9900	C48—H48	0.9500
C2—H2B	0.9900	C48—C49	1.378 (6)
C2—O1	1.416 (4)	C49—H49	0.9500
C3—H3A	0.9900	C49—C50	1.375 (6)
C3—H3B	0.9900	C50—H50	0.9500
C3—C42	1.510 (5)	C50—N42	1.334 (5)
C3—O1	1.430 (4)	N11—N12	1.365 (4)
C11—H11	0.9500	N21—N22	1.356 (4)
C11—C12	1.357 (5)	N31—N32	1.351 (4)
C11—N12	1.356 (4)	N41—Ag1^ii	2.329 (3)
C12—H12	0.9500	N42—Ag1^ii	2.291 (3)
C12—C13	1.391 (6)	B1A—F1A	1.376 (6)
C13—H13	0.9500	B1A—F2A	1.359 (6)
C13—N11	1.326 (5)	B1A—F3A	1.354 (7)
C21—H21	0.9500	B1A—F4A	1.408 (8)
C21—C22	1.349 (6)	B1B—F1B	1.372 (13)
C21—N22	1.357 (5)	B1B—F2B	1.343 (14)
C22—H22	0.9500	B1B—F3B	1.358 (14)
C22—C23	1.382 (6)	B1B—F4B	1.402 (15)
C23—H23	0.9500	C1S—H1SA	0.9800
C23—N21	1.314 (5)	C1S—H1SB	0.9800
C31—H31	0.9500	C1S—H1SC	0.9800
C31—C32	1.362 (5)	C1S—C2S	1.497 (10)
C31—N32	1.359 (4)	C2S—H2SA	0.9900
C32—H32	0.9500	C2S—H2SB	0.9900
C32—C33	1.391 (6)	C2S—O1S	1.418 (10)
C33—H33	0.9500	O1S—C3S	1.373 (10)
C33—N31	1.331 (5)	C3S—H3SA	0.9900
C41—H41	0.9500	C3S—H3SB	0.9900
C41—C42	1.390 (5)	C3S—C4S	1.491 (10)
C41—N41	1.337 (4)	C4S—H4SA	0.9800
C42—C43	1.383 (5)	C4S—H4SB	0.9800
C43—H43	0.9500	C4S—H4SC	0.9800
C43—C44	1.383 (5)
N11—Ag1—N21	82.19 (11)	C48—C47—H47	120.3
N11—Ag1—N41^i	124.33 (10)	C47—C48—H48	120.3
N11—Ag1—N42^i	141.87 (11)	C49—C48—C47	119.4 (4)
N21—Ag1—N41^i	133.39 (10)	C49—C48—H48	120.3
N42^i—Ag1—N21	111.93 (11)	C48—C49—H49	121.2
N42^i—Ag1—N41^i	72.32 (10)	C50—C49—C48	117.7 (4)
N12—C1—C2	110.4 (3)	C50—C49—H49	121.2
N12—C1—N22	111.1 (3)	C49—C50—H50	117.9
N12—C1—N32	108.7 (2)	N42—C50—C49	124.2 (4)
N22—C1—C2	108.8 (3)	N42—C50—H50	117.9
N22—C1—N32	108.4 (3)	C13—N11—Ag1	127.8 (3)
N32—C1—C2	109.4 (3)	C13—N11—N12	104.6 (3)
C1—C2—H2A	110.2	N12—N11—Ag1	123.5 (2)
C1—C2—H2B	110.2	C11—N12—C1	128.2 (3)
H2A—C2—H2B	108.5	C11—N12—N11	111.2 (3)
O1—C2—C1	107.4 (3)	N11—N12—C1	120.5 (3)
O1—C2—H2A	110.2	C23—N21—Ag1	129.9 (3)
O1—C2—H2B	110.2	C23—N21—N22	105.1 (3)
H3A—C3—H3B	107.9	N22—N21—Ag1	123.7 (2)
C42—C3—H3A	109.3	C21—N22—C1	128.8 (3)
C42—C3—H3B	109.3	N21—N22—C1	120.4 (3)
O1—C3—H3A	109.3	N21—N22—C21	110.5 (3)
O1—C3—H3B	109.3	C33—N31—N32	103.9 (3)
O1—C3—C42	111.8 (3)	C31—N32—C1	127.9 (3)
C12—C11—H11	126.5	N31—N32—C1	117.6 (3)
N12—C11—H11	126.5	N31—N32—C31	112.7 (3)
N12—C11—C12	107.1 (3)	C41—N41—Ag1^ii	124.9 (2)
C11—C12—H12	127.2	C41—N41—C45	118.7 (3)
C11—C12—C13	105.5 (3)	C45—N41—Ag1^ii	115.0 (2)
C13—C12—H12	127.2	C46—N42—Ag1^ii	117.1 (2)
C12—C13—H13	124.2	C50—N42—Ag1^ii	124.5 (3)
N11—C13—C12	111.7 (3)	C50—N42—C46	118.3 (3)
N11—C13—H13	124.2	C2—O1—C3	111.9 (3)
C22—C21—H21	126.4	F1A—B1A—F4A	106.7 (5)
C22—C21—N22	107.2 (4)	F2A—B1A—F1A	113.1 (5)
N22—C21—H21	126.4	F2A—B1A—F4A	108.2 (5)
C21—C22—H22	127.2	F3A—B1A—F1A	110.1 (5)
C21—C22—C23	105.5 (4)	F3A—B1A—F2A	113.1 (5)
C23—C22—H22	127.2	F3A—B1A—F4A	105.1 (5)
C22—C23—H23	124.2	F1B—B1B—F4B	112.9 (18)
N21—C23—C22	111.6 (4)	F2B—B1B—F1B	110.5 (17)
N21—C23—H23	124.2	F2B—B1B—F3B	117 (2)
C32—C31—H31	127.1	F2B—B1B—F4B	103.0 (17)
N32—C31—H31	127.1	F3B—B1B—F1B	107.3 (18)
N32—C31—C32	105.9 (3)	F3B—B1B—F4B	105.9 (18)
C31—C32—H32	127.1	H1SA—C1S—H1SB	109.5
C31—C32—C33	105.7 (3)	H1SA—C1S—H1SC	109.5
C33—C32—H32	127.1	H1SB—C1S—H1SC	109.5
C32—C33—H33	124.1	C2S—C1S—H1SA	109.5
N31—C33—C32	111.8 (3)	C2S—C1S—H1SB	109.5
N31—C33—H33	124.1	C2S—C1S—H1SC	109.5
C42—C41—H41	118.0	C1S—C2S—H2SA	107.6
N41—C41—H41	118.0	C1S—C2S—H2SB	107.6
N41—C41—C42	123.9 (3)	H2SA—C2S—H2SB	107.0
C41—C42—C3	119.9 (3)	O1S—C2S—C1S	119.0 (18)
C43—C42—C3	123.1 (3)	O1S—C2S—H2SA	107.6
C43—C42—C41	116.9 (3)	O1S—C2S—H2SB	107.6
C42—C43—H43	119.9	C3S—O1S—C2S	124.8 (19)
C42—C43—C44	120.1 (3)	O1S—C3S—H3SA	105.6
C44—C43—H43	119.9	O1S—C3S—H3SB	105.6
C43—C44—H44	120.3	O1S—C3S—C4S	126.7 (17)
C43—C44—C45	119.3 (3)	H3SA—C3S—H3SB	106.1
C45—C44—H44	120.3	C4S—C3S—H3SA	105.6
C44—C45—C46	121.8 (3)	C4S—C3S—H3SB	105.6
N41—C45—C44	121.0 (3)	C3S—C4S—H4SA	109.5
N41—C45—C46	117.2 (3)	C3S—C4S—H4SB	109.5
C47—C46—C45	122.2 (3)	C3S—C4S—H4SC	109.5
N42—C46—C45	116.7 (3)	H4SA—C4S—H4SB	109.5
N42—C46—C47	121.1 (3)	H4SA—C4S—H4SC	109.5
C46—C47—H47	120.3	H4SB—C4S—H4SC	109.5
C48—C47—C46	119.4 (4)
Ag1—N11—N12—C1	−18.6 (4)	C44—C45—N41—Ag1^ii	164.6 (3)
Ag1—N11—N12—C11	158.3 (2)	C44—C45—N41—C41	−2.4 (5)
Ag1—N21—N22—C1	16.2 (4)	C45—C46—C47—C48	−178.1 (3)
Ag1—N21—N22—C21	−168.7 (3)	C45—C46—N42—Ag1^ii	−4.9 (4)
C1—C2—O1—C3	171.6 (3)	C45—C46—N42—C50	179.4 (3)
C2—C1—N12—C11	12.4 (4)	C46—C45—N41—Ag1^ii	−14.8 (4)
C2—C1—N12—N11	−171.3 (3)	C46—C45—N41—C41	178.2 (3)
C2—C1—N22—C21	−2.1 (5)	C46—C47—C48—C49	−1.4 (6)
C2—C1—N22—N21	172.0 (3)	C47—C46—N42—Ag1^ii	175.0 (3)
C2—C1—N32—C31	91.1 (4)	C47—C46—N42—C50	−0.7 (5)
C2—C1—N32—N31	−72.4 (4)	C47—C48—C49—C50	−0.3 (6)
C3—C42—C43—C44	−176.7 (4)	C48—C49—C50—N42	1.7 (7)
C11—C12—C13—N11	−1.1 (5)	C49—C50—N42—Ag1^ii	−176.6 (3)
C12—C11—N12—C1	176.4 (3)	C49—C50—N42—C46	−1.2 (6)
C12—C11—N12—N11	−0.2 (4)	N12—C1—C2—O1	59.5 (3)
C12—C13—N11—Ag1	−156.6 (3)	N12—C1—N22—C21	119.6 (4)
C12—C13—N11—N12	0.9 (4)	N12—C1—N22—N21	−66.2 (4)
C13—N11—N12—C1	−177.3 (3)	N12—C1—N32—C31	−29.6 (4)
C13—N11—N12—C11	−0.4 (4)	N12—C1—N32—N31	166.9 (3)
C21—C22—C23—N21	0.3 (6)	N12—C11—C12—C13	0.8 (4)
C22—C21—N22—C1	175.3 (4)	N22—C1—C2—O1	−178.4 (3)
C22—C21—N22—N21	0.7 (5)	N22—C1—N12—C11	−108.4 (4)
C22—C23—N21—Ag1	167.3 (3)	N22—C1—N12—N11	67.9 (4)
C22—C23—N21—N22	0.1 (5)	N22—C1—N32—C31	−150.4 (3)
C23—N21—N22—C1	−175.6 (3)	N22—C1—N32—N31	46.1 (4)
C23—N21—N22—C21	−0.5 (5)	N22—C21—C22—C23	−0.6 (6)
C31—C32—C33—N31	0.1 (5)	N32—C1—C2—O1	−60.1 (3)
C32—C31—N32—C1	−166.8 (3)	N32—C1—N12—C11	132.4 (3)
C32—C31—N32—N31	−2.7 (4)	N32—C1—N12—N11	−51.3 (4)
C32—C33—N31—N32	−1.6 (4)	N32—C1—N22—C21	−121.0 (4)
C33—N31—N32—C1	168.6 (3)	N32—C1—N22—N21	53.1 (4)
C33—N31—N32—C31	2.7 (4)	N32—C31—C32—C33	1.5 (4)
C41—C42—C43—C44	−0.4 (6)	N41—C41—C42—C3	176.2 (3)
C42—C3—O1—C2	−87.7 (4)	N41—C41—C42—C43	−0.2 (5)
C42—C41—N41—Ag1^ii	−164.0 (3)	N41—C45—C46—C47	−166.5 (3)
C42—C41—N41—C45	1.7 (5)	N41—C45—C46—N42	13.4 (4)
C42—C43—C44—C45	−0.4 (6)	N42—C46—C47—C48	2.0 (5)
C43—C44—C45—C46	−178.8 (3)	O1—C3—C42—C41	163.7 (3)
C43—C44—C45—N41	1.8 (5)	O1—C3—C42—C43	−20.1 (5)
C44—C45—C46—C47	14.1 (5)	C1S—C2S—O1S—C3S	−160 (2)
C44—C45—C46—N42	−165.9 (3)	C2S—O1S—C3S—C4S	−130 (2)

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

(re) Bromidotricarbonyl(5-{[tris(pyrazol-1-yl)methoxy]methyl}-2,2'-bipyridine-κ²N,N')rhenium(I)

Crystal data

[ReBr(C22H20N8O)(CO)3]	Z = 2
Mr = 762.60	F(000) = 736
Triclinic, P1	Dx = 1.970 Mg m^−3
a = 8.8322 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4361 (7) Å	Cell parameters from 2374 reflections
c = 14.4346 (9) Å	θ = 2.9–22.7°
α = 67.708 (1)°	µ = 6.33 mm^−1
β = 73.552 (1)°	T = 150 K
γ = 89.664 (1)°	Plate, yellow
V = 1285.31 (13) Å^3	0.24 × 0.06 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4548 independent reflections
Radiation source: sealed tube	3788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −9→10
Tmin = 0.544, Tmax = 1.000	k = −13→13
10082 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0365P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
4548 reflections	Δρmax = 1.42 e Å^−3
352 parameters	Δρmin = −0.72 e Å^−3

Special details

Experimental. SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0810 before and 0.0417 after correction. The Ratio of minimum to maximum transmission is 0.5441. The λ/2 correction factor is 0.0015.

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.

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

	x	y	z	Uiso*/Ueq
Re1	0.05600 (3)	0.43384 (3)	0.28939 (2)	0.02184 (10)
Br1	0.23161 (8)	0.63200 (6)	0.12988 (5)	0.02573 (18)
C1	0.6317 (9)	−0.0231 (7)	0.2489 (6)	0.0316 (18)
C2	0.6153 (9)	0.0587 (7)	0.1404 (6)	0.0366 (19)
H2A	0.7088	0.1235	0.0988	0.044*
H2B	0.6089	0.0047	0.1016	0.044*
C3	0.3933 (9)	0.1314 (7)	0.0819 (5)	0.0284 (17)
H3A	0.3560	0.0461	0.0889	0.034*
H3B	0.4663	0.1765	0.0098	0.034*
C11	0.4307 (9)	0.0247 (6)	0.3866 (5)	0.0272 (17)
H11	0.3526	−0.0457	0.4106	0.033*
C12	0.4136 (9)	0.1262 (6)	0.4141 (6)	0.0318 (18)
H12	0.3234	0.1418	0.4605	0.038*
C13	0.5584 (10)	0.2022 (7)	0.3589 (6)	0.036 (2)
H13	0.5822	0.2803	0.3635	0.043*
C21	0.5498 (10)	−0.2478 (6)	0.3809 (6)	0.0352 (19)
H21	0.6274	−0.2553	0.4163	0.042*
C22	0.4279 (10)	−0.3360 (7)	0.4058 (7)	0.040 (2)
H22	0.4023	−0.4181	0.4612	0.048*
C23	0.3488 (9)	−0.2803 (7)	0.3329 (7)	0.041 (2)
H23	0.2566	−0.3212	0.3315	0.050*
C31	0.8886 (9)	−0.0388 (7)	0.2988 (6)	0.0353 (19)
H31	0.8603	−0.0124	0.3558	0.042*
C32	1.0272 (11)	−0.0805 (7)	0.2618 (8)	0.050 (2)
H32	1.1170	−0.0880	0.2867	0.060*
C33	1.0114 (10)	−0.1099 (7)	0.1803 (7)	0.046 (2)
H33	1.0911	−0.1435	0.1409	0.056*
C41	−0.2420 (9)	0.5505 (6)	0.2304 (6)	0.0300 (18)
H41	−0.2397	0.5919	0.2760	0.036*
C42	−0.3623 (9)	0.5683 (7)	0.1845 (6)	0.0320 (18)
H42	−0.4389	0.6238	0.1964	0.038*
C43	−0.3708 (9)	0.5049 (6)	0.1211 (5)	0.0298 (17)
H43	−0.4563	0.5123	0.0922	0.036*
C44	−0.2529 (9)	0.4310 (6)	0.1007 (5)	0.0276 (17)
H44	−0.2541	0.3897	0.0549	0.033*
C45	−0.1309 (8)	0.4163 (6)	0.1474 (5)	0.0235 (16)
C46	0.0000 (8)	0.3414 (6)	0.1298 (5)	0.0224 (16)
C47	0.0177 (8)	0.2793 (6)	0.0609 (5)	0.0229 (16)
H47	−0.0575	0.2847	0.0240	0.028*
C48	0.1435 (9)	0.2107 (6)	0.0469 (5)	0.0250 (16)
H48	0.1548	0.1676	0.0010	0.030*
C49	0.2547 (8)	0.2042 (6)	0.0997 (5)	0.0255 (16)
C50	0.2312 (8)	0.2674 (6)	0.1669 (5)	0.0248 (16)
H50	0.3048	0.2623	0.2049	0.030*
C51	0.2289 (8)	0.4076 (6)	0.3470 (5)	0.0230 (16)
C52	−0.0235 (8)	0.5284 (7)	0.3732 (5)	0.0270 (17)
C53	−0.0569 (9)	0.2801 (7)	0.4036 (6)	0.0284 (17)
N11	0.6595 (7)	0.1544 (5)	0.2993 (5)	0.0325 (15)
N12	0.5762 (7)	0.0410 (5)	0.3199 (4)	0.0275 (14)
N21	0.4143 (8)	−0.1641 (6)	0.2649 (5)	0.0367 (16)
N22	0.5401 (7)	−0.1468 (5)	0.2960 (5)	0.0265 (14)
N31	0.8724 (8)	−0.0860 (6)	0.1633 (6)	0.0443 (18)
N32	0.7985 (7)	−0.0422 (5)	0.2379 (5)	0.0298 (15)
N41	−0.1276 (7)	0.4763 (5)	0.2126 (4)	0.0236 (13)
N42	0.1076 (6)	0.3363 (5)	0.1807 (4)	0.0208 (13)
O1	0.4747 (6)	0.1188 (5)	0.1561 (4)	0.0372 (13)
O51	0.3305 (6)	0.3970 (4)	0.3850 (4)	0.0319 (12)
O52	−0.0790 (7)	0.5864 (5)	0.4219 (4)	0.0399 (14)
O53	−0.1132 (7)	0.1886 (5)	0.4705 (5)	0.0470 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01888 (17)	0.02660 (16)	0.02189 (17)	0.00424 (12)	−0.00667 (12)	−0.01119 (12)
Br1	0.0245 (4)	0.0274 (4)	0.0260 (4)	0.0041 (3)	−0.0084 (3)	−0.0107 (3)
C1	0.027 (5)	0.031 (4)	0.036 (5)	0.009 (4)	−0.015 (4)	−0.009 (4)
C2	0.032 (5)	0.039 (4)	0.032 (5)	0.010 (4)	−0.004 (4)	−0.012 (4)
C3	0.028 (5)	0.033 (4)	0.026 (4)	0.007 (3)	−0.008 (4)	−0.015 (3)
C11	0.022 (4)	0.028 (4)	0.028 (4)	0.000 (3)	−0.003 (3)	−0.010 (3)
C12	0.034 (5)	0.031 (4)	0.027 (4)	0.011 (4)	−0.008 (4)	−0.008 (3)
C13	0.037 (5)	0.025 (4)	0.049 (5)	0.009 (4)	−0.012 (4)	−0.018 (4)
C21	0.047 (6)	0.026 (4)	0.038 (5)	0.006 (4)	−0.024 (4)	−0.010 (4)
C22	0.039 (5)	0.026 (4)	0.054 (6)	0.003 (4)	−0.010 (4)	−0.017 (4)
C23	0.021 (5)	0.046 (5)	0.068 (6)	0.003 (4)	−0.012 (4)	−0.034 (5)
C31	0.022 (5)	0.033 (4)	0.042 (5)	0.003 (4)	−0.013 (4)	−0.003 (4)
C32	0.033 (6)	0.036 (5)	0.068 (7)	0.008 (4)	−0.017 (5)	−0.005 (5)
C33	0.023 (5)	0.029 (4)	0.077 (7)	0.012 (4)	0.000 (5)	−0.022 (5)
C41	0.027 (5)	0.031 (4)	0.030 (4)	0.007 (3)	−0.003 (4)	−0.015 (3)
C42	0.018 (4)	0.033 (4)	0.039 (5)	0.012 (3)	−0.006 (4)	−0.010 (4)
C43	0.023 (4)	0.033 (4)	0.027 (4)	0.003 (3)	−0.006 (4)	−0.007 (3)
C44	0.027 (4)	0.032 (4)	0.025 (4)	0.005 (3)	−0.011 (3)	−0.009 (3)
C45	0.016 (4)	0.026 (4)	0.019 (4)	0.001 (3)	0.001 (3)	−0.003 (3)
C46	0.016 (4)	0.022 (3)	0.025 (4)	−0.001 (3)	−0.005 (3)	−0.006 (3)
C47	0.028 (4)	0.021 (3)	0.023 (4)	0.002 (3)	−0.012 (3)	−0.008 (3)
C48	0.031 (4)	0.022 (3)	0.023 (4)	0.001 (3)	−0.011 (3)	−0.008 (3)
C49	0.019 (4)	0.027 (4)	0.029 (4)	0.005 (3)	−0.004 (3)	−0.012 (3)
C50	0.018 (4)	0.026 (4)	0.026 (4)	0.002 (3)	−0.005 (3)	−0.008 (3)
C51	0.017 (4)	0.027 (4)	0.020 (4)	−0.005 (3)	0.007 (3)	−0.014 (3)
C52	0.017 (4)	0.039 (4)	0.020 (4)	−0.007 (3)	−0.004 (3)	−0.008 (3)
C53	0.024 (4)	0.039 (4)	0.029 (4)	0.010 (4)	−0.014 (4)	−0.016 (4)
N11	0.028 (4)	0.022 (3)	0.042 (4)	0.002 (3)	−0.006 (3)	−0.010 (3)
N12	0.022 (4)	0.028 (3)	0.028 (3)	0.007 (3)	−0.006 (3)	−0.008 (3)
N21	0.025 (4)	0.038 (4)	0.063 (5)	0.011 (3)	−0.022 (4)	−0.032 (4)
N22	0.018 (3)	0.033 (3)	0.038 (4)	0.009 (3)	−0.014 (3)	−0.021 (3)
N31	0.025 (4)	0.046 (4)	0.071 (5)	0.007 (3)	−0.005 (4)	−0.039 (4)
N32	0.015 (3)	0.029 (3)	0.042 (4)	0.005 (3)	−0.006 (3)	−0.013 (3)
N41	0.018 (3)	0.026 (3)	0.027 (3)	0.004 (3)	−0.006 (3)	−0.012 (3)
N42	0.015 (3)	0.021 (3)	0.021 (3)	−0.001 (2)	−0.004 (3)	−0.003 (2)
O1	0.036 (3)	0.047 (3)	0.039 (3)	0.030 (3)	−0.021 (3)	−0.021 (3)
O51	0.027 (3)	0.034 (3)	0.040 (3)	0.007 (2)	−0.013 (3)	−0.017 (2)
O52	0.048 (4)	0.049 (3)	0.032 (3)	0.019 (3)	−0.013 (3)	−0.024 (3)
O53	0.045 (4)	0.043 (3)	0.040 (4)	−0.004 (3)	−0.008 (3)	−0.006 (3)

Geometric parameters (Å, º)

Re1—Br1	2.6274 (8)	C31—C32	1.351 (11)
Re1—C51	1.907 (8)	C31—N32	1.353 (9)
Re1—C52	1.905 (7)	C32—H32	0.9500
Re1—C53	1.922 (8)	C32—C33	1.383 (13)
Re1—N41	2.167 (6)	C33—H33	0.9500
Re1—N42	2.198 (5)	C33—N31	1.325 (10)
C1—C2	1.538 (10)	C41—H41	0.9500
C1—N12	1.452 (9)	C41—C42	1.379 (10)
C1—N22	1.446 (9)	C41—N41	1.346 (8)
C1—N32	1.461 (9)	C42—H42	0.9500
C2—H2A	0.9900	C42—C43	1.382 (10)
C2—H2B	0.9900	C43—H43	0.9500
C2—O1	1.419 (8)	C43—C44	1.375 (9)
C3—H3A	0.9900	C44—H44	0.9500
C3—H3B	0.9900	C44—C45	1.402 (10)
C3—C49	1.494 (9)	C45—C46	1.457 (9)
C3—O1	1.415 (8)	C45—N41	1.365 (8)
C11—H11	0.9500	C46—C47	1.402 (9)
C11—C12	1.357 (9)	C46—N42	1.345 (8)
C11—N12	1.334 (9)	C47—H47	0.9500
C12—H12	0.9500	C47—C48	1.369 (9)
C12—C13	1.391 (10)	C48—H48	0.9500
C13—H13	0.9500	C48—C49	1.389 (10)
C13—N11	1.324 (9)	C49—C50	1.387 (9)
C21—H21	0.9500	C50—H50	0.9500
C21—C22	1.350 (11)	C50—N42	1.356 (8)
C21—N22	1.351 (9)	C51—O51	1.161 (8)
C22—H22	0.9500	C52—O52	1.152 (8)
C22—C23	1.380 (11)	C53—O53	1.114 (8)
C23—H23	0.9500	N11—N12	1.380 (8)
C23—N21	1.327 (10)	N21—N22	1.352 (8)
C31—H31	0.9500	N31—N32	1.357 (8)
C51—Re1—Br1	88.42 (19)	C33—C32—H32	127.1
C51—Re1—C53	88.5 (3)	C32—C33—H33	123.8
C51—Re1—N41	175.2 (2)	N31—C33—C32	112.4 (7)
C51—Re1—N42	104.2 (2)	N31—C33—H33	123.8
C52—Re1—Br1	93.9 (2)	C42—C41—H41	118.9
C52—Re1—C51	87.2 (3)	N41—C41—H41	118.9
C52—Re1—C53	90.1 (3)	N41—C41—C42	122.2 (7)
C52—Re1—N41	93.5 (3)	C41—C42—H42	120.2
C52—Re1—N42	168.6 (3)	C41—C42—C43	119.7 (7)
C53—Re1—Br1	174.8 (2)	C43—C42—H42	120.2
C53—Re1—N41	96.2 (3)	C42—C43—H43	120.7
C53—Re1—N42	91.0 (2)	C44—C43—C42	118.6 (7)
N41—Re1—Br1	86.84 (15)	C44—C43—H43	120.7
N41—Re1—N42	75.1 (2)	C43—C44—H44	119.9
N42—Re1—Br1	85.76 (13)	C43—C44—C45	120.2 (7)
N12—C1—C2	109.5 (6)	C45—C44—H44	119.9
N12—C1—N32	109.8 (6)	C44—C45—C46	124.3 (6)
N22—C1—C2	112.8 (6)	N41—C45—C44	120.2 (6)
N22—C1—N12	107.5 (6)	N41—C45—C46	115.5 (6)
N22—C1—N32	108.0 (5)	C47—C46—C45	122.3 (6)
N32—C1—C2	109.1 (6)	N42—C46—C45	117.2 (6)
C1—C2—H2A	110.1	N42—C46—C47	120.5 (6)
C1—C2—H2B	110.1	C46—C47—H47	120.1
H2A—C2—H2B	108.4	C48—C47—C46	119.8 (6)
O1—C2—C1	108.0 (6)	C48—C47—H47	120.1
O1—C2—H2A	110.1	C47—C48—H48	119.9
O1—C2—H2B	110.1	C47—C48—C49	120.1 (6)
H3A—C3—H3B	108.2	C49—C48—H48	119.9
C49—C3—H3A	109.7	C48—C49—C3	119.5 (6)
C49—C3—H3B	109.7	C50—C49—C3	122.9 (7)
O1—C3—H3A	109.7	C50—C49—C48	117.6 (6)
O1—C3—H3B	109.7	C49—C50—H50	118.7
O1—C3—C49	109.8 (5)	N42—C50—C49	122.7 (7)
C12—C11—H11	126.0	N42—C50—H50	118.7
N12—C11—H11	126.0	O51—C51—Re1	175.6 (6)
N12—C11—C12	108.0 (6)	O52—C52—Re1	176.1 (6)
C11—C12—H12	127.8	O53—C53—Re1	175.5 (7)
C11—C12—C13	104.3 (6)	C13—N11—N12	102.9 (6)
C13—C12—H12	127.8	C11—N12—C1	126.9 (6)
C12—C13—H13	123.5	C11—N12—N11	111.7 (6)
N11—C13—C12	113.0 (6)	N11—N12—C1	118.7 (6)
N11—C13—H13	123.5	C23—N21—N22	102.6 (6)
C22—C21—H21	126.6	C21—N22—C1	127.3 (6)
C22—C21—N22	106.9 (7)	C21—N22—N21	112.5 (6)
N22—C21—H21	126.6	N21—N22—C1	119.5 (6)
C21—C22—H22	127.7	C33—N31—N32	103.1 (7)
C21—C22—C23	104.6 (7)	C31—N32—C1	130.3 (6)
C23—C22—H22	127.7	C31—N32—N31	112.8 (6)
C22—C23—H23	123.3	N31—N32—C1	116.3 (6)
N21—C23—C22	113.3 (7)	C41—N41—Re1	124.3 (5)
N21—C23—H23	123.3	C41—N41—C45	119.0 (6)
C32—C31—H31	127.0	C45—N41—Re1	116.5 (4)
C32—C31—N32	105.9 (8)	C46—N42—Re1	115.3 (4)
N32—C31—H31	127.0	C46—N42—C50	119.3 (6)
C31—C32—H32	127.1	C50—N42—Re1	125.3 (5)
C31—C32—C33	105.8 (8)	C3—O1—C2	113.8 (5)
C1—C2—O1—C3	−144.3 (6)	C45—C46—N42—Re1	3.6 (7)
C2—C1—N12—C11	94.0 (9)	C45—C46—N42—C50	179.8 (6)
C2—C1—N12—N11	−65.6 (8)	C46—C45—N41—Re1	−6.0 (7)
C2—C1—N22—C21	167.7 (7)	C46—C45—N41—C41	178.1 (6)
C2—C1—N22—N21	−22.6 (9)	C46—C47—C48—C49	−0.9 (10)
C2—C1—N32—C31	137.8 (7)	C47—C46—N42—Re1	−178.0 (5)
C2—C1—N32—N31	−51.6 (8)	C47—C46—N42—C50	−1.8 (9)
C3—C49—C50—N42	178.1 (6)	C47—C48—C49—C3	−178.7 (6)
C11—C12—C13—N11	1.0 (9)	C47—C48—C49—C50	0.9 (10)
C12—C11—N12—C1	−161.9 (6)	C48—C49—C50—N42	−1.4 (10)
C12—C11—N12—N11	−1.1 (8)	C49—C3—O1—C2	−175.7 (6)
C12—C13—N11—N12	−1.6 (8)	C49—C50—N42—Re1	177.7 (5)
C13—N11—N12—C1	164.2 (6)	C49—C50—N42—C46	1.9 (9)
C13—N11—N12—C11	1.6 (8)	N12—C1—C2—O1	−36.3 (8)
C21—C22—C23—N21	0.1 (9)	N12—C1—N22—C21	−71.4 (9)
C22—C21—N22—C1	171.4 (7)	N12—C1—N22—N21	98.3 (7)
C22—C21—N22—N21	1.1 (9)	N12—C1—N32—C31	17.8 (10)
C22—C23—N21—N22	0.5 (9)	N12—C1—N32—N31	−171.6 (6)
C23—N21—N22—C1	−172.1 (6)	N12—C11—C12—C13	0.1 (8)
C23—N21—N22—C21	−1.0 (8)	N22—C1—C2—O1	83.5 (8)
C31—C32—C33—N31	1.5 (10)	N22—C1—N12—C11	−29.0 (9)
C32—C31—N32—C1	171.5 (7)	N22—C1—N12—N11	171.5 (6)
C32—C31—N32—N31	0.7 (9)	N22—C1—N32—C31	−99.2 (8)
C32—C33—N31—N32	−1.0 (9)	N22—C1—N32—N31	71.4 (8)
C33—N31—N32—C1	−172.0 (6)	N22—C21—C22—C23	−0.7 (9)
C33—N31—N32—C31	0.2 (8)	N32—C1—C2—O1	−156.5 (6)
C41—C42—C43—C44	−3.7 (10)	N32—C1—N12—C11	−146.2 (7)
C42—C41—N41—Re1	−175.8 (5)	N32—C1—N12—N11	54.2 (8)
C42—C41—N41—C45	−0.3 (10)	N32—C1—N22—C21	47.1 (9)
C42—C43—C44—C45	2.8 (10)	N32—C1—N22—N21	−143.2 (6)
C43—C44—C45—C46	−179.2 (6)	N32—C31—C32—C33	−1.2 (9)
C43—C44—C45—N41	−0.6 (10)	N41—C41—C42—C43	2.5 (11)
C44—C45—C46—C47	1.8 (10)	N41—C45—C46—C47	−176.8 (6)
C44—C45—C46—N42	−179.8 (6)	N41—C45—C46—N42	1.5 (9)
C44—C45—N41—Re1	175.2 (5)	N42—C46—C47—C48	1.3 (10)
C44—C45—N41—C41	−0.7 (9)	O1—C3—C49—C48	−169.9 (6)
C45—C46—C47—C48	179.6 (6)	O1—C3—C49—C50	10.5 (9)