(2,2'-Bipyridine-6,6'-dicarboxyl-ato-κN,N',O)(6'-carb-oxy-2,2'-bipyridine-6-carboxyl-ato-κN,N',O)rhodium(III).

The Rh(III) ion in the title compound, [Rh(C(12)H(6)N(2)O(4))(C(12)H(7)N(2)O(4))], is coordinated by four N atoms and two O atoms from two chelating ligands L and HL (H(2)L = 2,2'-bipyridine-6,6'-dicarb-oxy-lic acid) to form a distorted octa-hedral geometry. Face-to-face π-stacking inter-actions are observed between inversion-related pyridine rings, with a centroid-to-centroid distance of 3.581 (1) Å [the perpendicular distance between the rings is 3.3980 (7) Å]. Inter-molecular O-H⋯O hydrogen bonds link adjacent mol-ecules into one-dimensional supra-molecular chains along the c axis, while several inter-molecular C-H⋯O inter-actions are also observed.

Related literature

For structures and photophysical properties of Ln III (Ln is a lanthanide) complexes with the title ligand, see: Bünzli et al. (2000 ▶). For Rh complexes with pyridyl triazole ligands, see: Burke et al. (2004 ▶). For an Mn–Rh coordination polymer with the 2-methyl­pyrazine-5-carb­oxy­lic acid ligand, see: Chapman et al. (2002 ▶). For a catena-poly diaqua CdII complex with the title ligand, see: Knight et al. (2006 ▶). For a review reporting the properties of coordination polymer networks via O and N atoms, see: Robin & Fromm (2006 ▶). For the structures and thermal properties of five Ln complexes with the title ligand, see: Wang et al. (2010 ▶). For a related NiII complex with the title ligand, see: Wang et al. (2009 ▶).

Experimental

Crystal data

[Rh(C12H6N2O4)(C12H7N2O4)]

M = 588.29

Monoclinic,

a = 9.3308 (4) Å

b = 13.6186 (6) Å

c = 16.9974 (8) Å

β = 100.696 (1)°

V = 2122.37 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.87 mm−1

T = 296 K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

15424 measured reflections

5269 independent reflections

4714 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.061

S = 1.03

5269 reflections

335 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004850/zq2151sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004850/zq2151Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Rh(C12H6N2O4)(C12H7N2O4)]	Z = 4
Mr = 588.29	F(000) = 1176
Monoclinic, P21/c	Dx = 1.841 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3308 (4) Å	µ = 0.87 mm−1
b = 13.6186 (6) Å	T = 296 K
c = 16.9974 (8) Å	Block, orange
β = 100.696 (1)°	0.2 × 0.2 × 0.2 mm
V = 2122.37 (16) Å3

Bruker APEXII CCD area-detector diffractometer	4714 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −10→12
15424 measured reflections	k = −17→18
5269 independent reflections	l = −22→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0317P)2 + 1.1072P] where P = (Fo2 + 2Fc2)/3
5269 reflections	(Δ/σ)max < 0.001
335 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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

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

	x	y	z	Uiso*/Ueq
Rh1	0.159112 (14)	0.237745 (9)	0.067212 (7)	0.02121 (5)
N1	0.08891 (15)	0.12682 (10)	0.12226 (8)	0.0225 (3)
N2	0.24130 (15)	0.12072 (10)	0.01055 (8)	0.0237 (3)
O5	−0.02277 (15)	0.23972 (9)	−0.01957 (8)	0.0298 (3)
N4	0.19640 (17)	0.35997 (10)	0.01389 (9)	0.0265 (3)
C6	0.20550 (18)	0.03125 (12)	0.03847 (10)	0.0250 (3)
C5	0.11551 (18)	0.03481 (12)	0.10163 (10)	0.0241 (3)
O1	0.05205 (14)	0.31499 (9)	0.13993 (8)	0.0287 (3)
N3	0.35387 (16)	0.27865 (11)	0.13906 (9)	0.0261 (3)
O4	0.26900 (19)	0.24099 (12)	−0.14737 (10)	0.0473 (4)
H4	0.3000	0.2889	−0.1681	0.071*
C4	0.0559 (2)	−0.04235 (13)	0.13826 (11)	0.0298 (4)
H4A	0.0739	−0.1071	0.1258	0.036*
C21	−0.0203 (2)	0.25889 (13)	0.18174 (12)	0.0297 (4)
C11	0.0918 (2)	0.38968 (13)	−0.04605 (11)	0.0299 (4)
O7	0.32750 (17)	0.11501 (10)	0.27890 (8)	0.0415 (3)
C20	0.4329 (2)	0.23263 (13)	0.20224 (11)	0.0297 (4)
O8	0.42615 (17)	0.06416 (10)	0.17725 (9)	0.0409 (3)
C24	0.3925 (2)	0.12843 (13)	0.21996 (11)	0.0299 (4)
O3	0.4556 (2)	0.26903 (12)	−0.04658 (11)	0.0534 (4)
O6	−0.13732 (17)	0.33511 (12)	−0.11836 (9)	0.0457 (4)
C1	0.00247 (19)	0.14967 (13)	0.17412 (10)	0.0257 (3)
C15	0.3070 (2)	0.41706 (13)	0.04922 (11)	0.0305 (4)
C3	−0.0313 (2)	−0.02061 (14)	0.19393 (11)	0.0330 (4)
H3	−0.0709	−0.0715	0.2195	0.040*
C7	0.2492 (2)	−0.05583 (13)	0.00854 (11)	0.0314 (4)
H7	0.2245	−0.1157	0.0287	0.038*
C9	0.3635 (2)	0.03691 (15)	−0.08131 (12)	0.0344 (4)
H9	0.4161	0.0403	−0.1227	0.041*
C16	0.3976 (2)	0.37045 (13)	0.11932 (12)	0.0308 (4)
C23	−0.0336 (2)	0.31820 (14)	−0.06556 (11)	0.0317 (4)
C8	0.3306 (2)	−0.05271 (15)	−0.05210 (12)	0.0349 (4)
H8	0.3623	−0.1104	−0.0726	0.042*
O2	−0.10279 (18)	0.29013 (11)	0.22277 (11)	0.0498 (4)
C18	0.5979 (2)	0.36721 (17)	0.22862 (14)	0.0457 (5)
H18	0.6798	0.3969	0.2588	0.055*
C2	−0.0601 (2)	0.07623 (14)	0.21197 (11)	0.0320 (4)
H2	−0.1199	0.0909	0.2485	0.038*
C13	0.2164 (3)	0.54139 (15)	−0.04621 (14)	0.0434 (5)
H13	0.2255	0.6030	−0.0684	0.052*
C10	0.31789 (19)	0.12252 (13)	−0.04881 (11)	0.0277 (3)
C14	0.3194 (2)	0.51125 (14)	0.01885 (14)	0.0399 (5)
H14	0.3949	0.5527	0.0417	0.048*
C12	0.1004 (2)	0.48196 (14)	−0.07888 (12)	0.0386 (4)
H12	0.0303	0.5034	−0.1216	0.046*
C19	0.5562 (2)	0.27527 (16)	0.24857 (14)	0.0419 (5)
H19	0.6092	0.2420	0.2922	0.050*
C22	0.3551 (2)	0.22076 (15)	−0.08135 (11)	0.0321 (4)
C17	0.5179 (2)	0.41533 (15)	0.16363 (13)	0.0400 (5)
H17	0.5452	0.4778	0.1499	0.048*

	U11	U22	U33	U12	U13	U23
Rh1	0.02553 (8)	0.01557 (7)	0.02292 (7)	−0.00143 (4)	0.00549 (5)	−0.00021 (4)
N1	0.0264 (7)	0.0176 (6)	0.0235 (7)	−0.0014 (5)	0.0043 (5)	0.0010 (5)
N2	0.0262 (7)	0.0203 (6)	0.0246 (7)	−0.0007 (5)	0.0046 (6)	−0.0018 (5)
O5	0.0323 (7)	0.0257 (6)	0.0296 (7)	−0.0020 (5)	0.0010 (5)	0.0006 (5)
N4	0.0340 (8)	0.0190 (7)	0.0284 (7)	−0.0008 (6)	0.0108 (6)	0.0010 (5)
C6	0.0266 (8)	0.0215 (8)	0.0258 (8)	−0.0009 (6)	0.0021 (7)	−0.0012 (6)
C5	0.0275 (8)	0.0195 (7)	0.0240 (8)	−0.0005 (6)	0.0014 (6)	−0.0003 (6)
O1	0.0349 (7)	0.0197 (6)	0.0336 (7)	0.0008 (5)	0.0119 (5)	−0.0026 (5)
N3	0.0277 (7)	0.0221 (7)	0.0289 (7)	−0.0024 (6)	0.0063 (6)	−0.0041 (6)
O4	0.0565 (10)	0.0437 (9)	0.0410 (9)	−0.0150 (7)	0.0075 (7)	0.0115 (6)
C4	0.0366 (10)	0.0196 (8)	0.0317 (9)	−0.0019 (7)	0.0019 (7)	0.0027 (7)
C21	0.0312 (9)	0.0253 (8)	0.0332 (9)	−0.0002 (7)	0.0079 (7)	−0.0035 (7)
C11	0.0402 (10)	0.0248 (8)	0.0268 (9)	0.0052 (7)	0.0114 (7)	0.0022 (7)
O7	0.0612 (9)	0.0309 (7)	0.0357 (7)	0.0079 (7)	0.0174 (7)	0.0000 (6)
C20	0.0286 (9)	0.0299 (9)	0.0299 (9)	0.0033 (7)	0.0038 (7)	−0.0067 (7)
O8	0.0523 (9)	0.0313 (7)	0.0405 (8)	0.0085 (6)	0.0122 (7)	−0.0078 (6)
C24	0.0309 (9)	0.0282 (9)	0.0279 (9)	0.0074 (7)	−0.0017 (7)	−0.0018 (7)
O3	0.0542 (10)	0.0489 (10)	0.0556 (10)	−0.0211 (8)	0.0065 (8)	−0.0042 (8)
O6	0.0470 (9)	0.0529 (9)	0.0332 (7)	0.0040 (7)	−0.0036 (6)	0.0070 (7)
C1	0.0287 (8)	0.0245 (8)	0.0241 (8)	−0.0007 (6)	0.0054 (7)	−0.0010 (6)
C15	0.0354 (10)	0.0216 (8)	0.0375 (10)	−0.0036 (7)	0.0147 (8)	−0.0020 (7)
C3	0.0392 (10)	0.0278 (9)	0.0321 (9)	−0.0053 (7)	0.0072 (8)	0.0079 (7)
C7	0.0356 (10)	0.0226 (8)	0.0348 (10)	0.0005 (7)	0.0036 (8)	−0.0027 (7)
C9	0.0336 (10)	0.0385 (11)	0.0330 (10)	0.0039 (8)	0.0109 (8)	−0.0068 (8)
C16	0.0324 (9)	0.0247 (8)	0.0374 (10)	−0.0050 (7)	0.0116 (8)	−0.0067 (7)
C23	0.0390 (10)	0.0301 (9)	0.0266 (9)	0.0047 (8)	0.0080 (8)	−0.0009 (7)
C8	0.0359 (10)	0.0306 (10)	0.0379 (10)	0.0073 (8)	0.0057 (8)	−0.0094 (8)
O2	0.0586 (10)	0.0346 (8)	0.0667 (11)	0.0002 (7)	0.0390 (9)	−0.0092 (7)
C18	0.0322 (10)	0.0469 (13)	0.0547 (13)	−0.0081 (9)	−0.0003 (9)	−0.0187 (10)
C2	0.0367 (10)	0.0336 (9)	0.0275 (9)	−0.0027 (8)	0.0109 (7)	0.0024 (7)
C13	0.0599 (14)	0.0240 (9)	0.0528 (13)	0.0031 (9)	0.0273 (11)	0.0111 (8)
C10	0.0272 (8)	0.0289 (9)	0.0272 (8)	−0.0008 (7)	0.0054 (7)	−0.0024 (7)
C14	0.0459 (12)	0.0233 (9)	0.0554 (13)	−0.0066 (8)	0.0224 (10)	0.0000 (8)
C12	0.0537 (12)	0.0296 (10)	0.0354 (10)	0.0080 (9)	0.0159 (9)	0.0084 (8)
C19	0.0343 (10)	0.0438 (12)	0.0427 (12)	0.0021 (9)	−0.0055 (9)	−0.0096 (9)
C22	0.0350 (10)	0.0329 (10)	0.0328 (10)	−0.0022 (7)	0.0179 (8)	−0.0034 (7)
C17	0.0366 (11)	0.0323 (10)	0.0518 (12)	−0.0106 (8)	0.0101 (9)	−0.0113 (9)

Rh1—N1	1.9529 (13)	C20—C24	1.513 (3)
Rh1—N4	1.9571 (14)	O8—C24	1.215 (2)
Rh1—O1	2.0226 (12)	O3—C22	1.206 (3)
Rh1—O5	2.0316 (13)	O6—C23	1.213 (2)
Rh1—N3	2.0689 (15)	C1—C2	1.377 (2)
Rh1—N2	2.0808 (14)	C15—C14	1.396 (3)
N1—C5	1.337 (2)	C15—C16	1.471 (3)
N1—C1	1.337 (2)	C3—C2	1.391 (3)
N2—C10	1.341 (2)	C3—H3	0.9300
N2—C6	1.371 (2)	C7—C8	1.390 (3)
O5—C23	1.317 (2)	C7—H7	0.9300
N4—C11	1.336 (2)	C9—C8	1.374 (3)
N4—C15	1.342 (2)	C9—C10	1.390 (3)
C6—C7	1.382 (2)	C9—H9	0.9300
C6—C5	1.481 (2)	C16—C17	1.374 (3)
C5—C4	1.389 (2)	C8—H8	0.9300
O1—C21	1.313 (2)	C18—C19	1.372 (3)
N3—C20	1.340 (2)	C18—C17	1.379 (3)
N3—C16	1.376 (2)	C18—H18	0.9300
O4—C22	1.283 (3)	C2—H2	0.9300
O4—H4	0.8200	C13—C12	1.382 (3)
C4—C3	1.389 (3)	C13—C14	1.386 (3)
C4—H4A	0.9300	C13—H13	0.9300
C21—O2	1.208 (2)	C10—C22	1.513 (3)
C21—C1	1.512 (2)	C14—H14	0.9300
C11—C12	1.383 (3)	C12—H12	0.9300
C11—C23	1.511 (3)	C19—H19	0.9300
O7—C24	1.277 (2)	C17—H17	0.9300
C20—C19	1.394 (3)
N1—Rh1—N4	169.74 (6)	N1—C1—C2	119.94 (16)
N1—Rh1—O1	82.06 (5)	N1—C1—C21	113.40 (15)
N4—Rh1—O1	89.49 (5)	C2—C1—C21	126.61 (16)
N1—Rh1—O5	92.80 (5)	N4—C15—C14	118.48 (18)
N4—Rh1—O5	81.31 (6)	N4—C15—C16	113.04 (15)
O1—Rh1—O5	89.77 (5)	C14—C15—C16	128.44 (18)
N1—Rh1—N3	105.16 (6)	C4—C3—C2	120.91 (17)
N4—Rh1—N3	80.34 (6)	C4—C3—H3	119.5
O1—Rh1—N3	88.77 (5)	C2—C3—H3	119.5
O5—Rh1—N3	161.60 (5)	C6—C7—C8	119.09 (18)
N1—Rh1—N2	79.31 (6)	C6—C7—H7	120.5
N4—Rh1—N2	108.94 (6)	C8—C7—H7	120.5
O1—Rh1—N2	161.35 (5)	C8—C9—C10	119.73 (18)
O5—Rh1—N2	90.23 (5)	C8—C9—H9	120.1
N3—Rh1—N2	96.93 (6)	C10—C9—H9	120.1
C5—N1—C1	123.71 (15)	C17—C16—N3	121.32 (19)
C5—N1—Rh1	120.29 (12)	C17—C16—C15	122.71 (17)
C1—N1—Rh1	115.65 (11)	N3—C16—C15	115.96 (16)
C10—N2—C6	118.36 (15)	O6—C23—O5	123.79 (19)
C10—N2—Rh1	128.91 (12)	O6—C23—C11	121.25 (18)
C6—N2—Rh1	112.71 (11)	O5—C23—C11	114.92 (16)
C23—O5—Rh1	113.81 (12)	C9—C8—C7	119.00 (17)
C11—N4—C15	123.93 (15)	C9—C8—H8	120.5
C11—N4—Rh1	116.31 (12)	C7—C8—H8	120.5
C15—N4—Rh1	118.27 (12)	C19—C18—C17	119.67 (19)
N2—C6—C7	121.85 (16)	C19—C18—H18	120.2
N2—C6—C5	115.40 (14)	C17—C18—H18	120.2
C7—C6—C5	122.74 (15)	C1—C2—C3	118.00 (17)
N1—C5—C4	118.83 (16)	C1—C2—H2	121.0
N1—C5—C6	112.24 (14)	C3—C2—H2	121.0
C4—C5—C6	128.90 (15)	C12—C13—C14	121.48 (18)
C21—O1—Rh1	112.97 (10)	C12—C13—H13	119.3
C20—N3—C16	118.43 (16)	C14—C13—H13	119.3
C20—N3—Rh1	129.77 (12)	N2—C10—C9	121.95 (17)
C16—N3—Rh1	111.63 (12)	N2—C10—C22	118.83 (16)
C22—O4—H4	109.5	C9—C10—C22	119.23 (16)
C5—C4—C3	118.54 (16)	C13—C14—C15	118.33 (19)
C5—C4—H4A	120.7	C13—C14—H14	120.8
C3—C4—H4A	120.7	C15—C14—H14	120.8
O2—C21—O1	123.68 (17)	C13—C12—C11	118.02 (19)
O2—C21—C1	120.73 (17)	C13—C12—H12	121.0
O1—C21—C1	115.58 (15)	C11—C12—H12	121.0
N4—C11—C12	119.57 (18)	C18—C19—C20	118.9 (2)
N4—C11—C23	113.49 (15)	C18—C19—H19	120.6
C12—C11—C23	126.69 (18)	C20—C19—H19	120.6
N3—C20—C19	122.11 (18)	O3—C22—O4	128.0 (2)
N3—C20—C24	118.53 (16)	O3—C22—C10	120.88 (19)
C19—C20—C24	119.22 (18)	O4—C22—C10	111.14 (16)
O8—C24—O7	125.35 (18)	C16—C17—C18	119.59 (19)
O8—C24—C20	117.09 (17)	C16—C17—H17	120.2
O7—C24—C20	117.56 (16)	C18—C17—H17	120.2
N4—Rh1—N1—C5	142.4 (3)	Rh1—N4—C11—C12	170.67 (14)
O1—Rh1—N1—C5	177.26 (13)	C15—N4—C11—C23	−169.87 (16)
O5—Rh1—N1—C5	87.88 (13)	Rh1—N4—C11—C23	−4.10 (19)
N3—Rh1—N1—C5	−96.19 (13)	C16—N3—C20—C19	0.7 (3)
N2—Rh1—N1—C5	−1.83 (12)	Rh1—N3—C20—C19	−174.12 (15)
N4—Rh1—N1—C1	−31.0 (4)	C16—N3—C20—C24	−174.99 (16)
O1—Rh1—N1—C1	3.86 (12)	Rh1—N3—C20—C24	10.2 (2)
O5—Rh1—N1—C1	−85.52 (12)	N3—C20—C24—O8	75.6 (2)
N3—Rh1—N1—C1	90.41 (13)	C19—C20—C24—O8	−100.2 (2)
N2—Rh1—N1—C1	−175.23 (13)	N3—C20—C24—O7	−105.1 (2)
N1—Rh1—N2—C10	178.45 (16)	C19—C20—C24—O7	79.0 (2)
N4—Rh1—N2—C10	4.76 (16)	C5—N1—C1—C2	2.6 (3)
O1—Rh1—N2—C10	175.62 (15)	Rh1—N1—C1—C2	175.79 (13)
O5—Rh1—N2—C10	85.64 (15)	C5—N1—C1—C21	−174.92 (15)
N3—Rh1—N2—C10	−77.37 (15)	Rh1—N1—C1—C21	−1.77 (19)
N1—Rh1—N2—C6	0.49 (11)	O2—C21—C1—N1	175.54 (19)
N4—Rh1—N2—C6	−173.19 (11)	O1—C21—C1—N1	−3.0 (2)
O1—Rh1—N2—C6	−2.3 (2)	O2—C21—C1—C2	−1.8 (3)
O5—Rh1—N2—C6	−92.31 (12)	O1—C21—C1—C2	179.66 (17)
N3—Rh1—N2—C6	104.68 (12)	C11—N4—C15—C14	−4.0 (3)
N1—Rh1—O5—C23	168.90 (13)	Rh1—N4—C15—C14	−169.55 (14)
N4—Rh1—O5—C23	−2.66 (12)	C11—N4—C15—C16	173.52 (16)
O1—Rh1—O5—C23	86.86 (12)	Rh1—N4—C15—C16	8.0 (2)
N3—Rh1—O5—C23	1.4 (2)	C5—C4—C3—C2	0.9 (3)
N2—Rh1—O5—C23	−111.79 (13)	N2—C6—C7—C8	−0.6 (3)
N1—Rh1—N4—C11	−51.6 (4)	C5—C6—C7—C8	178.45 (16)
O1—Rh1—N4—C11	−86.07 (13)	C20—N3—C16—C17	−1.0 (3)
O5—Rh1—N4—C11	3.78 (12)	Rh1—N3—C16—C17	174.67 (15)
N3—Rh1—N4—C11	−174.92 (13)	C20—N3—C16—C15	179.72 (16)
N2—Rh1—N4—C11	91.02 (13)	Rh1—N3—C16—C15	−4.57 (19)
N1—Rh1—N4—C15	115.0 (3)	N4—C15—C16—C17	178.97 (17)
O1—Rh1—N4—C15	80.54 (13)	C14—C15—C16—C17	−3.8 (3)
O5—Rh1—N4—C15	170.39 (14)	N4—C15—C16—N3	−1.8 (2)
N3—Rh1—N4—C15	−8.30 (13)	C14—C15—C16—N3	175.46 (18)
N2—Rh1—N4—C15	−102.37 (13)	Rh1—O5—C23—O6	−176.56 (16)
C10—N2—C6—C7	1.6 (2)	Rh1—O5—C23—C11	1.25 (19)
Rh1—N2—C6—C7	179.84 (14)	N4—C11—C23—O6	179.66 (17)
C10—N2—C6—C5	−177.49 (15)	C12—C11—C23—O6	5.3 (3)
Rh1—N2—C6—C5	0.70 (18)	N4—C11—C23—O5	1.8 (2)
C1—N1—C5—C4	−2.9 (3)	C12—C11—C23—O5	−172.54 (18)
Rh1—N1—C5—C4	−175.79 (12)	C10—C9—C8—C7	1.4 (3)
C1—N1—C5—C6	175.50 (15)	C6—C7—C8—C9	−0.9 (3)
Rh1—N1—C5—C6	2.7 (2)	N1—C1—C2—C3	−0.5 (3)
N2—C6—C5—N1	−2.1 (2)	C21—C1—C2—C3	176.71 (18)
C7—C6—C5—N1	178.79 (16)	C4—C3—C2—C1	−1.2 (3)
N2—C6—C5—C4	176.16 (17)	C6—N2—C10—C9	−1.2 (3)
C7—C6—C5—C4	−3.0 (3)	Rh1—N2—C10—C9	−179.03 (13)
N1—Rh1—O1—C21	−5.47 (13)	C6—N2—C10—C22	178.66 (15)
N4—Rh1—O1—C21	168.69 (13)	Rh1—N2—C10—C22	0.8 (2)
O5—Rh1—O1—C21	87.39 (13)	C8—C9—C10—N2	−0.3 (3)
N3—Rh1—O1—C21	−110.96 (13)	C8—C9—C10—C22	179.85 (18)
N2—Rh1—O1—C21	−2.7 (2)	C12—C13—C14—C15	2.5 (3)
N1—Rh1—N3—C20	10.65 (17)	N4—C15—C14—C13	0.3 (3)
N4—Rh1—N3—C20	−178.22 (16)	C16—C15—C14—C13	−176.87 (19)
O1—Rh1—N3—C20	92.09 (16)	C14—C13—C12—C11	−1.7 (3)
O5—Rh1—N3—C20	177.68 (16)	N4—C11—C12—C13	−1.9 (3)
N2—Rh1—N3—C20	−70.10 (16)	C23—C11—C12—C13	172.14 (18)
N1—Rh1—N3—C16	−164.44 (12)	C17—C18—C19—C20	0.0 (3)
N4—Rh1—N3—C16	6.69 (12)	N3—C20—C19—C18	−0.2 (3)
O1—Rh1—N3—C16	−83.00 (12)	C24—C20—C19—C18	175.48 (19)
O5—Rh1—N3—C16	2.6 (2)	N2—C10—C22—O3	79.9 (2)
N2—Rh1—N3—C16	114.81 (12)	C9—C10—C22—O3	−100.3 (2)
N1—C5—C4—C3	1.1 (3)	N2—C10—C22—O4	−100.8 (2)
C6—C5—C4—C3	−177.02 (17)	C9—C10—C22—O4	79.0 (2)
Rh1—O1—C21—O2	−172.48 (18)	N3—C16—C17—C18	0.9 (3)
Rh1—O1—C21—C1	6.0 (2)	C15—C16—C17—C18	−179.95 (19)
C15—N4—C11—C12	4.9 (3)	C19—C18—C17—C16	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O7i	0.82	1.64	2.443 (2)	168
C2—H2···O6ii	0.93	2.51	3.326 (2)	147
C4—H4A···O5iii	0.93	2.54	3.341 (2)	145
C7—H7···O5iii	0.93	2.51	3.304 (2)	143
C9—H9···O8iv	0.93	2.36	3.097 (2)	136
C12—H12···O1v	0.93	2.59	3.194 (2)	123
C17—H17···O7vi	0.93	2.42	3.148 (2)	136

Rh1—N1	1.9529 (13)
Rh1—N4	1.9571 (14)
Rh1—O1	2.0226 (12)
Rh1—O5	2.0316 (13)
Rh1—N3	2.0689 (15)
Rh1—N2	2.0808 (14)

N2—C6—C5—N1	−2.1 (2)
N4—C15—C16—N3	−1.8 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O7i	0.82	1.64	2.443 (2)	168
C2—H2⋯O6ii	0.93	2.51	3.326 (2)	147
C4—H4A⋯O5iii	0.93	2.54	3.341 (2)	145
C7—H7⋯O5iii	0.93	2.51	3.304 (2)	143
C9—H9⋯O8iv	0.93	2.36	3.097 (2)	136
C12—H12⋯O1v	0.93	2.59	3.194 (2)	123
C17—H17⋯O7vi	0.93	2.42	3.148 (2)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .