Chlorido­[(1,2,5,6-η)-cyclo­octa-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-yl­idene)rhodium(I)

A new neutral triazole-based N-heterocyclic carbene rhodium(I) complex [RhCl(C₈H₁₂)(C₈H₁₅N₃)], has been synthesized and structurally characterized. The complex crystallizes with two mol­ecules in the asymmetric unit. The central rhodium(I) atom has a distorted square-planar coordination environment, formed by a cyclo­octa-1,5-diene (COD) ligand, an N-heterocyclic carbene (NHC) ligand, and a chlorido ligand. The bond lengths are unexceptional. A weak inter­molecular non-standard hydrogen-bonding inter­action exists between the chlorido and NHC ligands.

Computing details

Chlorido[(1,2,5,6-η)-cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)rhodium(I)

Crystal data

[RhCl(C8H12)(C8H15N3)]	Z = 4
Mr = 399.76	F(000) = 824
Triclinic, P1	Dx = 1.531 Mg m^−3
a = 9.6253 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.6771 (2) Å	Cell parameters from 36515 reflections
c = 13.7938 (2) Å	θ = 2.0–28.3°
α = 76.410 (1)°	µ = 1.14 mm^−1
β = 83.455 (1)°	T = 100 K
γ = 80.345 (1)°	Block, yellow
V = 1734.78 (4) Å^3	0.3 × 0.23 × 0.15 mm

Data collection

Rigaku XtaLAB Synergy-S diffractometer	7885 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.037
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2024)	h = −12→12
Tmin = 0.770, Tmax = 1.000	k = −18→18
52942 measured reflections	l = −17→18
8619 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0321P)^2 + 2.0009P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
8619 reflections	Δρmax = 1.02 e Å^−3
385 parameters	Δρmin = −0.50 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Rh1	0.35791 (2)	0.31385 (2)	0.72501 (2)	0.01343 (5)
Cl1	0.46921 (5)	0.44263 (3)	0.76187 (4)	0.01601 (9)
N1	0.63831 (18)	0.25377 (13)	0.61135 (13)	0.0179 (3)
N2	0.76467 (19)	0.18859 (15)	0.61666 (14)	0.0223 (4)
N3	0.62725 (18)	0.16069 (13)	0.75695 (13)	0.0163 (3)
C1	0.5521 (2)	0.23940 (15)	0.69543 (15)	0.0154 (4)
C2	0.7527 (2)	0.13252 (17)	0.70700 (16)	0.0212 (4)
H2	0.822845	0.078693	0.734610	0.025*
C3	0.6158 (2)	0.33469 (17)	0.52183 (16)	0.0214 (4)
H3A	0.514387	0.363675	0.521882	0.026*
H3B	0.641327	0.305673	0.461753	0.026*
C4	0.7029 (3)	0.41866 (19)	0.51641 (18)	0.0284 (5)
H4A	0.681758	0.472773	0.457157	0.043*
H4B	0.803667	0.391129	0.511948	0.043*
H4C	0.679746	0.446378	0.576607	0.043*
C5	0.5869 (2)	0.11712 (16)	0.86246 (15)	0.0184 (4)
H5A	0.579128	0.044357	0.870410	0.022*
H5B	0.493144	0.152359	0.882081	0.022*
C6	0.6947 (2)	0.12717 (16)	0.93138 (15)	0.0183 (4)
H6	0.789022	0.092337	0.909805	0.022*
C7	0.7068 (2)	0.23813 (17)	0.92465 (17)	0.0239 (4)
H7A	0.735865	0.269980	0.855600	0.036*
H7B	0.777314	0.242137	0.968970	0.036*
H7C	0.614982	0.273725	0.945043	0.036*
C8	0.6531 (3)	0.07327 (18)	1.03807 (16)	0.0255 (5)
H8A	0.559343	0.104992	1.059798	0.038*
H8B	0.722372	0.078770	1.082634	0.038*
H8C	0.650800	0.001393	1.040347	0.038*
C9	0.2598 (2)	0.18390 (16)	0.73460 (17)	0.0211 (4)
H9	0.326041	0.118340	0.745835	0.025*
C10	0.2672 (2)	0.24083 (17)	0.63539 (17)	0.0213 (4)
H10	0.337283	0.207878	0.589157	0.026*
C11	0.1444 (2)	0.31046 (19)	0.58410 (18)	0.0268 (5)
H11A	0.081133	0.268428	0.566191	0.032*
H11B	0.181354	0.353098	0.521253	0.032*
C12	0.0577 (2)	0.38023 (18)	0.64893 (18)	0.0249 (5)
H12A	0.012958	0.442801	0.604755	0.030*
H12B	−0.018645	0.345144	0.689358	0.030*
C13	0.1475 (2)	0.40917 (16)	0.71818 (17)	0.0200 (4)
H13	0.150599	0.483800	0.706192	0.024*
C14	0.1654 (2)	0.35721 (17)	0.81537 (16)	0.0201 (4)
H14	0.178421	0.401299	0.861133	0.024*
C15	0.1063 (2)	0.26155 (18)	0.86783 (18)	0.0268 (5)
H15A	0.004525	0.279333	0.886938	0.032*
H15B	0.154345	0.231383	0.930027	0.032*
C16	0.1241 (2)	0.18177 (17)	0.80330 (19)	0.0260 (5)
H16A	0.125068	0.113287	0.847610	0.031*
H16B	0.042164	0.194752	0.762303	0.031*
Rh1'	0.07480 (2)	0.19144 (2)	0.24861 (2)	0.01290 (5)
Cl1'	0.24607 (5)	0.13510 (4)	0.12636 (3)	0.01603 (9)
N1'	0.32141 (18)	0.18781 (13)	0.36507 (13)	0.0163 (3)
N2'	0.42244 (19)	0.24024 (14)	0.38413 (14)	0.0199 (4)
N3'	0.27156 (18)	0.33698 (13)	0.27928 (13)	0.0161 (3)
C1'	0.2285 (2)	0.24327 (15)	0.30092 (14)	0.0146 (4)
C2'	0.3879 (2)	0.33103 (16)	0.33006 (16)	0.0199 (4)
H2'	0.437503	0.386481	0.326262	0.024*
C3'	0.3287 (2)	0.07959 (16)	0.40976 (16)	0.0206 (4)
H3'A	0.241691	0.055764	0.398081	0.025*
H3'B	0.333658	0.068364	0.482920	0.025*
C4'	0.4562 (3)	0.01840 (17)	0.36624 (19)	0.0280 (5)
H4'A	0.449460	0.027066	0.294282	0.042*
H4'B	0.459312	−0.053659	0.398999	0.042*
H4'C	0.542437	0.042190	0.377272	0.042*
C5'	0.2110 (2)	0.42804 (15)	0.20818 (16)	0.0191 (4)
H5'A	0.251695	0.487350	0.216000	0.023*
H5'B	0.107738	0.440969	0.224727	0.023*
C6'	0.2383 (2)	0.41853 (16)	0.09956 (16)	0.0212 (4)
H6'	0.184237	0.365842	0.089419	0.025*
C7'	0.3940 (3)	0.3873 (2)	0.07214 (18)	0.0317 (5)
H7'A	0.449099	0.435015	0.087651	0.048*
H7'B	0.408573	0.388173	0.000483	0.048*
H7'C	0.424780	0.318609	0.110580	0.048*
C8'	0.1823 (3)	0.52123 (18)	0.03371 (19)	0.0342 (6)
H8'A	0.081581	0.539251	0.052492	0.051*
H8'B	0.195075	0.516551	−0.036648	0.051*
H8'C	0.234411	0.573581	0.043154	0.051*
C9'	−0.0801 (2)	0.28443 (15)	0.32074 (15)	0.0169 (4)
H9'	−0.041860	0.336934	0.345470	0.020*
C10'	−0.0575 (2)	0.18603 (15)	0.38251 (15)	0.0174 (4)
H10'	−0.005804	0.182107	0.442522	0.021*
C11'	−0.1593 (2)	0.10822 (17)	0.39879 (17)	0.0231 (4)
H11C	−0.256713	0.144488	0.390277	0.028*
H11D	−0.156544	0.067389	0.468255	0.028*
C12'	−0.1232 (2)	0.03646 (17)	0.32576 (18)	0.0243 (5)
H12C	−0.055371	−0.022884	0.355491	0.029*
H12D	−0.210286	0.011085	0.316728	0.029*
C13'	−0.0602 (2)	0.08679 (16)	0.22444 (16)	0.0196 (4)
H13'	−0.012685	0.038113	0.182806	0.023*
C14'	−0.1080 (2)	0.18225 (17)	0.16998 (16)	0.0205 (4)
H14'	−0.088014	0.190447	0.095986	0.025*
C15'	−0.2389 (2)	0.25045 (18)	0.20069 (18)	0.0241 (5)
H15C	−0.304485	0.208130	0.245477	0.029*
H15D	−0.287981	0.287450	0.140498	0.029*
C16'	−0.2006 (2)	0.32711 (16)	0.25459 (16)	0.0216 (4)
H16C	−0.174614	0.386987	0.204044	0.026*
H16D	−0.284902	0.350564	0.295974	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.01197 (8)	0.01211 (8)	0.01682 (8)	−0.00219 (5)	−0.00155 (5)	−0.00392 (5)
Cl1	0.0141 (2)	0.00959 (19)	0.0263 (2)	−0.00364 (16)	−0.00341 (17)	−0.00568 (17)
N1	0.0145 (8)	0.0195 (8)	0.0194 (8)	−0.0007 (7)	−0.0017 (6)	−0.0050 (7)
N2	0.0173 (9)	0.0253 (9)	0.0232 (9)	0.0030 (7)	−0.0012 (7)	−0.0080 (7)
N3	0.0149 (8)	0.0149 (8)	0.0191 (8)	−0.0008 (6)	−0.0019 (6)	−0.0047 (6)
C1	0.0161 (9)	0.0136 (9)	0.0184 (9)	−0.0043 (7)	−0.0020 (7)	−0.0056 (7)
C2	0.0172 (10)	0.0220 (10)	0.0247 (11)	0.0017 (8)	−0.0021 (8)	−0.0088 (8)
C3	0.0209 (10)	0.0252 (11)	0.0169 (10)	−0.0033 (8)	−0.0027 (8)	−0.0016 (8)
C4	0.0312 (12)	0.0287 (12)	0.0240 (11)	−0.0109 (10)	−0.0004 (9)	0.0003 (9)
C5	0.0187 (10)	0.0164 (9)	0.0191 (10)	−0.0048 (8)	−0.0014 (8)	−0.0007 (7)
C6	0.0163 (9)	0.0174 (9)	0.0206 (10)	−0.0024 (7)	−0.0025 (8)	−0.0028 (8)
C7	0.0254 (11)	0.0229 (11)	0.0253 (11)	−0.0077 (9)	−0.0052 (9)	−0.0047 (9)
C8	0.0266 (11)	0.0284 (12)	0.0209 (10)	−0.0092 (9)	−0.0040 (9)	0.0007 (9)
C9	0.0184 (10)	0.0169 (10)	0.0313 (11)	−0.0063 (8)	−0.0030 (8)	−0.0087 (8)
C10	0.0181 (10)	0.0224 (10)	0.0278 (11)	−0.0034 (8)	−0.0040 (8)	−0.0130 (9)
C11	0.0239 (11)	0.0333 (12)	0.0267 (11)	−0.0037 (9)	−0.0092 (9)	−0.0104 (10)
C12	0.0187 (10)	0.0267 (11)	0.0290 (12)	−0.0002 (9)	−0.0076 (9)	−0.0048 (9)
C13	0.0128 (9)	0.0180 (10)	0.0289 (11)	0.0019 (7)	−0.0010 (8)	−0.0076 (8)
C14	0.0157 (9)	0.0223 (10)	0.0229 (10)	−0.0012 (8)	0.0017 (8)	−0.0088 (8)
C15	0.0214 (11)	0.0294 (12)	0.0272 (11)	−0.0070 (9)	0.0043 (9)	−0.0023 (9)
C16	0.0199 (10)	0.0213 (11)	0.0359 (12)	−0.0078 (8)	−0.0003 (9)	−0.0021 (9)
Rh1'	0.01226 (8)	0.01255 (8)	0.01436 (8)	−0.00244 (5)	−0.00160 (5)	−0.00315 (5)
Cl1'	0.0145 (2)	0.0157 (2)	0.0178 (2)	−0.00018 (16)	0.00186 (17)	−0.00625 (17)
N1'	0.0162 (8)	0.0159 (8)	0.0177 (8)	−0.0057 (6)	−0.0035 (6)	−0.0020 (6)
N2'	0.0183 (8)	0.0200 (9)	0.0233 (9)	−0.0077 (7)	−0.0054 (7)	−0.0035 (7)
N3'	0.0165 (8)	0.0149 (8)	0.0170 (8)	−0.0050 (6)	−0.0014 (6)	−0.0021 (6)
C1'	0.0154 (9)	0.0139 (9)	0.0143 (9)	−0.0025 (7)	0.0012 (7)	−0.0039 (7)
C2'	0.0186 (10)	0.0203 (10)	0.0225 (10)	−0.0075 (8)	−0.0027 (8)	−0.0039 (8)
C3'	0.0223 (10)	0.0156 (10)	0.0228 (10)	−0.0061 (8)	−0.0075 (8)	0.0029 (8)
C4'	0.0267 (12)	0.0189 (11)	0.0391 (13)	−0.0010 (9)	−0.0125 (10)	−0.0048 (9)
C5'	0.0201 (10)	0.0132 (9)	0.0229 (10)	−0.0031 (8)	−0.0018 (8)	−0.0013 (8)
C6'	0.0290 (11)	0.0139 (9)	0.0209 (10)	−0.0038 (8)	−0.0056 (8)	−0.0020 (8)
C7'	0.0355 (13)	0.0318 (13)	0.0243 (12)	−0.0035 (10)	0.0067 (10)	−0.0046 (10)
C8'	0.0565 (17)	0.0180 (11)	0.0267 (12)	−0.0020 (11)	−0.0129 (11)	0.0002 (9)
C9'	0.0163 (9)	0.0172 (9)	0.0183 (9)	−0.0035 (7)	0.0022 (7)	−0.0073 (7)
C10'	0.0180 (9)	0.0182 (10)	0.0168 (9)	−0.0057 (8)	0.0018 (7)	−0.0049 (7)
C11'	0.0234 (11)	0.0214 (10)	0.0260 (11)	−0.0105 (9)	0.0043 (9)	−0.0062 (8)
C12'	0.0209 (10)	0.0198 (10)	0.0343 (12)	−0.0083 (8)	0.0044 (9)	−0.0092 (9)
C13'	0.0163 (9)	0.0211 (10)	0.0262 (11)	−0.0052 (8)	−0.0025 (8)	−0.0127 (8)
C14'	0.0165 (10)	0.0259 (11)	0.0227 (10)	−0.0025 (8)	−0.0054 (8)	−0.0111 (8)
C15'	0.0163 (10)	0.0277 (11)	0.0295 (12)	0.0024 (8)	−0.0072 (9)	−0.0098 (9)
C16'	0.0198 (10)	0.0196 (10)	0.0239 (11)	0.0019 (8)	−0.0004 (8)	−0.0059 (8)

Geometric parameters (Å, º)

Rh1—Cl1	2.3846 (5)	Rh1'—Cl1'	2.3887 (5)
Rh1—C1	2.020 (2)	Rh1'—C1'	2.012 (2)
Rh1—C9	2.120 (2)	Rh1'—C9'	2.110 (2)
Rh1—C10	2.099 (2)	Rh1'—C10'	2.114 (2)
Rh1—C13	2.216 (2)	Rh1'—C13'	2.190 (2)
Rh1—C14	2.189 (2)	Rh1'—C14'	2.205 (2)
N1—N2	1.380 (2)	N1'—N2'	1.382 (2)
N1—C1	1.342 (3)	N1'—C1'	1.340 (3)
N1—C3	1.461 (3)	N1'—C3'	1.457 (3)
N2—C2	1.305 (3)	N2'—C2'	1.301 (3)
N3—C1	1.361 (3)	N3'—C1'	1.369 (2)
N3—C2	1.364 (3)	N3'—C2'	1.369 (3)
N3—C5	1.471 (3)	N3'—C5'	1.471 (3)
C2—H2	0.9500	C2'—H2'	0.9500
C3—H3A	0.9900	C3'—H3'A	0.9900
C3—H3B	0.9900	C3'—H3'B	0.9900
C3—C4	1.515 (3)	C3'—C4'	1.514 (3)
C4—H4A	0.9800	C4'—H4'A	0.9800
C4—H4B	0.9800	C4'—H4'B	0.9800
C4—H4C	0.9800	C4'—H4'C	0.9800
C5—H5A	0.9900	C5'—H5'A	0.9900
C5—H5B	0.9900	C5'—H5'B	0.9900
C5—C6	1.527 (3)	C5'—C6'	1.524 (3)
C6—H6	1.0000	C6'—H6'	1.0000
C6—C7	1.522 (3)	C6'—C7'	1.517 (3)
C6—C8	1.525 (3)	C6'—C8'	1.532 (3)
C7—H7A	0.9800	C7'—H7'A	0.9800
C7—H7B	0.9800	C7'—H7'B	0.9800
C7—H7C	0.9800	C7'—H7'C	0.9800
C8—H8A	0.9800	C8'—H8'A	0.9800
C8—H8B	0.9800	C8'—H8'B	0.9800
C8—H8C	0.9800	C8'—H8'C	0.9800
C9—H9	1.0000	C9'—H9'	1.0000
C9—C10	1.407 (3)	C9'—C10'	1.411 (3)
C9—C16	1.524 (3)	C9'—C16'	1.511 (3)
C10—H10	1.0000	C10'—H10'	1.0000
C10—C11	1.517 (3)	C10'—C11'	1.527 (3)
C11—H11A	0.9900	C11'—H11C	0.9900
C11—H11B	0.9900	C11'—H11D	0.9900
C11—C12	1.540 (3)	C11'—C12'	1.539 (3)
C12—H12A	0.9900	C12'—H12C	0.9900
C12—H12B	0.9900	C12'—H12D	0.9900
C12—C13	1.516 (3)	C12'—C13'	1.513 (3)
C13—H13	1.0000	C13'—H13'	1.0000
C13—C14	1.377 (3)	C13'—C14'	1.377 (3)
C14—H14	1.0000	C14'—H14'	1.0000
C14—C15	1.507 (3)	C14'—C15'	1.519 (3)
C15—H15A	0.9900	C15'—H15C	0.9900
C15—H15B	0.9900	C15'—H15D	0.9900
C15—C16	1.540 (3)	C15'—C16'	1.532 (3)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
C1—Rh1—Cl1	88.36 (5)	C1'—Rh1'—Cl1'	88.57 (6)
C1—Rh1—C9	92.59 (8)	C1'—Rh1'—C9'	90.29 (8)
C1—Rh1—C10	91.43 (8)	C1'—Rh1'—C10'	93.67 (8)
C1—Rh1—C13	166.29 (8)	C1'—Rh1'—C13'	160.34 (8)
C1—Rh1—C14	157.23 (8)	C1'—Rh1'—C14'	163.12 (8)
C9—Rh1—Cl1	164.45 (6)	C9'—Rh1'—Cl1'	161.60 (6)
C9—Rh1—C13	89.51 (8)	C9'—Rh1'—C10'	39.02 (8)
C9—Rh1—C14	81.88 (8)	C9'—Rh1'—C13'	98.19 (8)
C10—Rh1—Cl1	156.57 (6)	C9'—Rh1'—C14'	81.70 (8)
C10—Rh1—C9	38.96 (9)	C10'—Rh1'—Cl1'	159.36 (6)
C10—Rh1—C13	81.72 (8)	C10'—Rh1'—C13'	82.22 (8)
C10—Rh1—C14	97.75 (8)	C10'—Rh1'—C14'	89.42 (8)
C13—Rh1—Cl1	93.23 (6)	C13'—Rh1'—Cl1'	88.80 (6)
C14—Rh1—Cl1	91.27 (6)	C13'—Rh1'—C14'	36.52 (8)
C14—Rh1—C13	36.43 (8)	C14'—Rh1'—Cl1'	94.37 (6)
N2—N1—C3	119.00 (17)	N2'—N1'—C3'	119.18 (16)
C1—N1—N2	114.16 (17)	C1'—N1'—N2'	114.54 (16)
C1—N1—C3	126.62 (18)	C1'—N1'—C3'	126.18 (17)
C2—N2—N1	102.62 (17)	C2'—N2'—N1'	102.61 (16)
C1—N3—C2	108.75 (17)	C1'—N3'—C5'	126.56 (17)
C1—N3—C5	126.42 (17)	C2'—N3'—C1'	108.60 (17)
C2—N3—C5	124.68 (18)	C2'—N3'—C5'	124.71 (17)
N1—C1—Rh1	129.32 (15)	N1'—C1'—Rh1'	125.97 (14)
N1—C1—N3	102.77 (17)	N1'—C1'—N3'	102.45 (16)
N3—C1—Rh1	127.91 (14)	N3'—C1'—Rh1'	131.50 (15)
N2—C2—N3	111.69 (19)	N2'—C2'—N3'	111.78 (18)
N2—C2—H2	124.2	N2'—C2'—H2'	124.1
N3—C2—H2	124.2	N3'—C2'—H2'	124.1
N1—C3—H3A	109.2	N1'—C3'—H3'A	109.3
N1—C3—H3B	109.2	N1'—C3'—H3'B	109.3
N1—C3—C4	111.92 (18)	N1'—C3'—C4'	111.53 (18)
H3A—C3—H3B	107.9	H3'A—C3'—H3'B	108.0
C4—C3—H3A	109.2	C4'—C3'—H3'A	109.3
C4—C3—H3B	109.2	C4'—C3'—H3'B	109.3
C3—C4—H4A	109.5	C3'—C4'—H4'A	109.5
C3—C4—H4B	109.5	C3'—C4'—H4'B	109.5
C3—C4—H4C	109.5	C3'—C4'—H4'C	109.5
H4A—C4—H4B	109.5	H4'A—C4'—H4'B	109.5
H4A—C4—H4C	109.5	H4'A—C4'—H4'C	109.5
H4B—C4—H4C	109.5	H4'B—C4'—H4'C	109.5
N3—C5—H5A	109.3	N3'—C5'—H5'A	108.9
N3—C5—H5B	109.3	N3'—C5'—H5'B	108.9
N3—C5—C6	111.69 (16)	N3'—C5'—C6'	113.21 (17)
H5A—C5—H5B	107.9	H5'A—C5'—H5'B	107.7
C6—C5—H5A	109.3	C6'—C5'—H5'A	108.9
C6—C5—H5B	109.3	C6'—C5'—H5'B	108.9
C5—C6—H6	108.3	C5'—C6'—H6'	108.7
C7—C6—C5	111.33 (17)	C5'—C6'—C8'	107.67 (18)
C7—C6—H6	108.3	C7'—C6'—C5'	111.82 (19)
C7—C6—C8	111.59 (18)	C7'—C6'—H6'	108.7
C8—C6—C5	109.01 (17)	C7'—C6'—C8'	111.1 (2)
C8—C6—H6	108.3	C8'—C6'—H6'	108.7
C6—C7—H7A	109.5	C6'—C7'—H7'A	109.5
C6—C7—H7B	109.5	C6'—C7'—H7'B	109.5
C6—C7—H7C	109.5	C6'—C7'—H7'C	109.5
H7A—C7—H7B	109.5	H7'A—C7'—H7'B	109.5
H7A—C7—H7C	109.5	H7'A—C7'—H7'C	109.5
H7B—C7—H7C	109.5	H7'B—C7'—H7'C	109.5
C6—C8—H8A	109.5	C6'—C8'—H8'A	109.5
C6—C8—H8B	109.5	C6'—C8'—H8'B	109.5
C6—C8—H8C	109.5	C6'—C8'—H8'C	109.5
H8A—C8—H8B	109.5	H8'A—C8'—H8'B	109.5
H8A—C8—H8C	109.5	H8'A—C8'—H8'C	109.5
H8B—C8—H8C	109.5	H8'B—C8'—H8'C	109.5
Rh1—C9—H9	114.1	Rh1'—C9'—H9'	113.9
C10—C9—Rh1	69.75 (12)	C10'—C9'—Rh1'	70.67 (12)
C10—C9—H9	114.1	C10'—C9'—H9'	113.9
C10—C9—C16	123.7 (2)	C10'—C9'—C16'	126.31 (19)
C16—C9—Rh1	113.47 (15)	C16'—C9'—Rh1'	109.39 (14)
C16—C9—H9	114.1	C16'—C9'—H9'	113.9
Rh1—C10—H10	113.9	Rh1'—C10'—H10'	113.7
C9—C10—Rh1	71.29 (12)	C9'—C10'—Rh1'	70.32 (11)
C9—C10—H10	113.9	C9'—C10'—H10'	113.7
C9—C10—C11	125.0 (2)	C9'—C10'—C11'	124.48 (19)
C11—C10—Rh1	110.99 (15)	C11'—C10'—Rh1'	113.29 (14)
C11—C10—H10	113.9	C11'—C10'—H10'	113.7
C10—C11—H11A	108.9	C10'—C11'—H11C	109.1
C10—C11—H11B	108.9	C10'—C11'—H11D	109.1
C10—C11—C12	113.42 (18)	C10'—C11'—C12'	112.48 (17)
H11A—C11—H11B	107.7	H11C—C11'—H11D	107.8
C12—C11—H11A	108.9	C12'—C11'—H11C	109.1
C12—C11—H11B	108.9	C12'—C11'—H11D	109.1
C11—C12—H12A	109.1	C11'—C12'—H12C	108.9
C11—C12—H12B	109.1	C11'—C12'—H12D	108.9
H12A—C12—H12B	107.9	H12C—C12'—H12D	107.7
C13—C12—C11	112.38 (18)	C13'—C12'—C11'	113.21 (18)
C13—C12—H12A	109.1	C13'—C12'—H12C	108.9
C13—C12—H12B	109.1	C13'—C12'—H12D	108.9
Rh1—C13—H13	114.2	Rh1'—C13'—H13'	114.2
C12—C13—Rh1	111.23 (14)	C12'—C13'—Rh1'	107.61 (14)
C12—C13—H13	114.2	C12'—C13'—H13'	114.2
C14—C13—Rh1	70.71 (12)	C14'—C13'—Rh1'	72.31 (12)
C14—C13—C12	124.2 (2)	C14'—C13'—C12'	125.9 (2)
C14—C13—H13	114.2	C14'—C13'—H13'	114.2
Rh1—C14—H14	113.9	Rh1'—C14'—H14'	114.1
C13—C14—Rh1	72.87 (12)	C13'—C14'—Rh1'	71.16 (12)
C13—C14—H14	113.9	C13'—C14'—H14'	114.1
C13—C14—C15	126.2 (2)	C13'—C14'—C15'	124.4 (2)
C15—C14—Rh1	107.91 (14)	C15'—C14'—Rh1'	111.23 (14)
C15—C14—H14	113.9	C15'—C14'—H14'	114.1
C14—C15—H15A	108.9	C14'—C15'—H15C	109.4
C14—C15—H15B	108.9	C14'—C15'—H15D	109.4
C14—C15—C16	113.18 (19)	C14'—C15'—C16'	111.22 (17)
H15A—C15—H15B	107.8	H15C—C15'—H15D	108.0
C16—C15—H15A	108.9	C16'—C15'—H15C	109.4
C16—C15—H15B	108.9	C16'—C15'—H15D	109.4
C9—C16—C15	112.07 (18)	C9'—C16'—C15'	113.46 (18)
C9—C16—H16A	109.2	C9'—C16'—H16C	108.9
C9—C16—H16B	109.2	C9'—C16'—H16D	108.9
C15—C16—H16A	109.2	C15'—C16'—H16C	108.9
C15—C16—H16B	109.2	C15'—C16'—H16D	108.9
H16A—C16—H16B	107.9	H16C—C16'—H16D	107.7
Rh1—C9—C10—C11	−103.0 (2)	Rh1'—C9'—C10'—C11'	−105.3 (2)
Rh1—C9—C16—C15	−12.6 (2)	Rh1'—C9'—C16'—C15'	39.8 (2)
Rh1—C10—C11—C12	−35.7 (2)	Rh1'—C10'—C11'—C12'	11.5 (2)
Rh1—C13—C14—C15	−100.0 (2)	Rh1'—C13'—C14'—C15'	−103.3 (2)
Rh1—C14—C15—C16	−37.0 (2)	Rh1'—C14'—C15'—C16'	15.3 (2)
N1—N2—C2—N3	−0.6 (2)	N1'—N2'—C2'—N3'	0.1 (2)
N2—N1—C1—Rh1	−179.85 (14)	N2'—N1'—C1'—Rh1'	175.92 (14)
N2—N1—C1—N3	−0.4 (2)	N2'—N1'—C1'—N3'	−1.1 (2)
N2—N1—C3—C4	−72.5 (2)	N2'—N1'—C3'—C4'	−67.9 (2)
N3—C5—C6—C7	61.0 (2)	N3'—C5'—C6'—C7'	−52.5 (2)
N3—C5—C6—C8	−175.51 (17)	N3'—C5'—C6'—C8'	−174.82 (19)
C1—N1—N2—C2	0.6 (2)	C1'—N1'—N2'—C2'	0.6 (2)
C1—N1—C3—C4	101.8 (2)	C1'—N1'—C3'—C4'	108.2 (2)
C1—N3—C2—N2	0.5 (3)	C1'—N3'—C2'—N2'	−0.8 (3)
C1—N3—C5—C6	−118.8 (2)	C1'—N3'—C5'—C6'	−68.1 (3)
C2—N3—C1—Rh1	179.44 (14)	C2'—N3'—C1'—Rh1'	−175.68 (16)
C2—N3—C1—N1	−0.1 (2)	C2'—N3'—C1'—N1'	1.1 (2)
C2—N3—C5—C6	56.2 (3)	C2'—N3'—C5'—C6'	107.3 (2)
C3—N1—N2—C2	175.61 (19)	C3'—N1'—N2'—C2'	177.21 (19)
C3—N1—C1—Rh1	5.6 (3)	C3'—N1'—C1'—Rh1'	−0.4 (3)
C3—N1—C1—N3	−174.88 (19)	C3'—N1'—C1'—N3'	−177.37 (19)
C5—N3—C1—Rh1	−4.9 (3)	C5'—N3'—C1'—Rh1'	0.3 (3)
C5—N3—C1—N1	175.64 (18)	C5'—N3'—C1'—N1'	177.04 (18)
C5—N3—C2—N2	−175.31 (18)	C5'—N3'—C2'—N2'	−176.84 (18)
C9—C10—C11—C12	45.6 (3)	C9'—C10'—C11'—C12'	92.9 (3)
C10—C9—C16—C15	−93.2 (3)	C10'—C9'—C16'—C15'	−40.0 (3)
C10—C11—C12—C13	31.7 (3)	C10'—C11'—C12'—C13'	−32.6 (3)
C11—C12—C13—Rh1	−12.7 (2)	C11'—C12'—C13'—Rh1'	36.5 (2)
C11—C12—C13—C14	−93.2 (3)	C11'—C12'—C13'—C14'	−44.0 (3)
C12—C13—C14—Rh1	103.1 (2)	C12'—C13'—C14'—Rh1'	99.3 (2)
C12—C13—C14—C15	3.1 (3)	C12'—C13'—C14'—C15'	−4.0 (3)
C13—C14—C15—C16	44.6 (3)	C13'—C14'—C15'—C16'	96.4 (2)
C14—C15—C16—C9	33.5 (3)	C14'—C15'—C16'—C9'	−36.4 (3)
C16—C9—C10—Rh1	105.3 (2)	C16'—C9'—C10'—Rh1'	100.3 (2)
C16—C9—C10—C11	2.4 (3)	C16'—C9'—C10'—C11'	−5.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2′—H2′···Cl1^i	0.95	2.62	3.502 (2)	155

Symmetry code: (i) −x+1, −y+1, −z+1.