{1,3-Bis(3,4,5-trimethoxy­benz­yl)-3,4,5,6-tetra­hydro­pyrimidin-2-yl­idene}chloro(η⁴-cyclo­octa-1,5-diene)rhodium(I)

In the title complex, [RhCl(C₈H₁₂)(C₂₄H₃₂N₂O₆)], the Rh atom is coordinated by a Cl atom, one C atom of the tetrahydropyrimidine ring and the two double bonds of cyclo­octa­diene. Each of the tetra­hydro­pyrimidine and cyclo­octa­diene rings is puckered.

Key indicators

• Single-crystal X-ray study
• T = 188 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.075
• wR factor = 0.182
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.60 Ratio

Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.152
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.15
PLAT213_ALERT_2_B Atom C7      has ADP max/min Ratio .............       4.80 prola
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C10

Alert level C
PLAT213_ALERT_2_C Atom C6      has ADP max/min Ratio .............       3.50 oblat
PLAT213_ALERT_2_C Atom C10     has ADP max/min Ratio .............       3.40 prola
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.79 Ratio
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C10    -   C11    ...       1.42 Ang.

   1 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

{1,3-Bis(3,4,5-trimethoxybenzyl)-3,4,5,6-tetrahydropyrimidin-2- ylidene}chloro(η⁴-cycloocta-1,5-diene)rhodium(I)

Crystal data

[RhCl(C8H12)(C24H32N2O6)]	F(000) = 1440
Mr = 691.05	Dx = 1.464 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10832 reflections
a = 10.175 (2) Å	θ = 2.2–26.0°
b = 22.289 (4) Å	µ = 0.68 mm^−1
c = 13.947 (3) Å	T = 188 K
β = 97.57 (3)°	Rod, yellow
V = 3135.5 (11) Å^3	0.24 × 0.08 × 0.05 mm
Z = 4

Data collection

Rigaku Mercury CCD (2x2 bin mode) diffractometer	5513 independent reflections
Radiation source: Sealed Tube	3705 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.152
Detector resolution: 14.6199 pixels mm^-1	θmax = 25.0°, θmin = 2.2°
dtprofit.ref scans	h = −12→12
Absorption correction: multi-scan (REQAB; Rigaku/MSC, 1999)	k = −25→26
Tmin = 0.855, Tmax = 0.967	l = −16→16
25658 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 5.4242P] where P = (Fo^2 + 2Fc^2)/3
5513 reflections	(Δ/σ)max = 0.001
385 parameters	Δρmax = 0.83 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Experimental. Spectroscopic analysis: ν_(CN) = 1592 cm^-1; ¹H NMR (399.9 MHz, CDCl₃, δ, p.p.m.): 6.91 [s, 4H, CH₂C₆H₂(OCH₃)₃-3,4,5], 6.83 (d, J = 14.0 Hz, 2H, CH_COD), 4.89 [m, 2H, CH₂C₆H₂(OCH₃)₃-3,4,5], 4.83 (d, J = 14.0 Hz, 2H, CH_COD], 3.88 [s, 12H, CH₂C₆H₂(OCH₃)₃-3,5], 3.83 [s, 6H, CH₂C₆H₂(OCH₃)₃-4], 3.36 [m, 2H, CH₂C₆H₂(OCH₃)₃-3,4,5],2.89 (t, J = 5.6 Hz, 4H, NCH₂CH₂CH₂N), 2.33 (m, 4H, CH_2COD), 1.87 (m, 4H, CH_2COD), 1.74 (quint., J = 5.6 Hz, 2H, NCH₂CH₂CH₂N); ¹³C NMR (100.5 MHz, CDCl₃, δ, p.p.m.): 206.9 (d, J = 45.7 Hz, C_carbene), 153.6, 137.7, 132.6 and 106.2 [CH₂C₆H₂(OCH₃)₃-3,4,5], 97.1 and 69.6 (d, J = 6.9 Hz and 15.3 Hz, CH_COD), 62.8 [CH₂C₆H₂(OCH₃)₃-3,4,5], 61.0 [CH₂C₆H₂(OCH₃)₃-4], 56.7 [CH₂C₆H₂(OCH₃)₃-3,5], 43.3 (NCH₂CH₂CH₂N), 32.8 and 29.0 (CH_2COD), 21.3 (NCH₂CH₂CH₂N).

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.

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

	x	y	z	Uiso*/Ueq
Rh1	0.65894 (6)	0.63252 (3)	0.31700 (4)	0.02232 (19)
Cl1	0.52468 (19)	0.64006 (9)	0.16255 (13)	0.0284 (4)
O1	0.2879 (6)	0.9377 (2)	0.3307 (5)	0.0388 (15)
O2	0.1273 (6)	0.8915 (2)	0.1812 (4)	0.0316 (13)
O3	0.1373 (6)	0.7754 (2)	0.1341 (4)	0.0338 (14)
O4	0.1492 (6)	0.4985 (2)	0.0618 (4)	0.0366 (15)
O5	0.1511 (6)	0.3800 (2)	0.0840 (4)	0.0312 (13)
O6	0.3050 (6)	0.3275 (2)	0.2308 (4)	0.0332 (14)
N1	0.4252 (6)	0.5781 (3)	0.3872 (5)	0.0252 (15)
N2	0.4381 (6)	0.6781 (3)	0.4202 (5)	0.0253 (15)
C1	0.2996 (9)	0.5716 (4)	0.4278 (6)	0.0308 (19)
H1A	0.2264	0.5777	0.3778	0.037*
H1B	0.2931	0.5317	0.4527	0.037*
C2	0.2932 (9)	0.6153 (4)	0.5054 (6)	0.033 (2)
H2A	0.3573	0.6050	0.5597	0.040*
H2B	0.2069	0.6140	0.5261	0.040*
C3	0.3203 (9)	0.6781 (4)	0.4721 (6)	0.0311 (19)
H3A	0.2448	0.6926	0.4300	0.037*
H3B	0.3353	0.7044	0.5269	0.037*
C4	0.4899 (7)	0.6303 (4)	0.3810 (5)	0.0203 (15)
C5	0.7769 (8)	0.6564 (4)	0.4470 (6)	0.0290 (19)
H5	0.7007	0.6772	0.4640	0.035*
C6	0.8960 (10)	0.6946 (5)	0.4299 (7)	0.052 (3)
H6A	0.8783	0.7354	0.4463	0.063*
H6B	0.9713	0.6814	0.4736	0.063*
C7	0.9311 (14)	0.6937 (8)	0.3330 (8)	0.092 (6)
H7A	1.0174	0.6759	0.3354	0.110*
H7B	0.9382	0.7345	0.3120	0.110*
C8	0.8390 (9)	0.6612 (5)	0.2582 (7)	0.042 (2)
H8	0.7825	0.6845	0.2117	0.050*
C9	0.8313 (9)	0.6002 (4)	0.2527 (7)	0.039 (2)
H9	0.7704	0.5838	0.2009	0.047*
C10	0.9071 (14)	0.5567 (7)	0.3185 (10)	0.084 (5)
H10A	0.8944	0.5175	0.2903	0.100*
H10B	0.9996	0.5663	0.3214	0.100*
C11	0.8760 (12)	0.5538 (5)	0.4146 (8)	0.056 (3)
H11A	0.9553	0.5622	0.4577	0.067*
H11B	0.8506	0.5133	0.4267	0.067*
C12	0.7683 (9)	0.5949 (4)	0.4403 (6)	0.035 (2)
H12	0.6869	0.5766	0.4531	0.042*
C13	0.4914 (8)	0.7384 (4)	0.4060 (7)	0.0313 (19)
H13A	0.5685	0.7349	0.3733	0.038*
H13B	0.5183	0.7565	0.4679	0.038*
C14	0.3906 (9)	0.7788 (4)	0.3472 (6)	0.0310 (19)
C15	0.3855 (8)	0.8390 (3)	0.3716 (6)	0.0243 (17)
H15	0.4416	0.8540	0.4271	0.029*
C16	0.2992 (9)	0.8779 (3)	0.3156 (6)	0.0321 (19)
C17	0.2139 (8)	0.8544 (3)	0.2368 (6)	0.0278 (18)
C18	0.2212 (8)	0.7932 (3)	0.2136 (5)	0.0232 (17)
C19	0.3099 (8)	0.7560 (3)	0.2682 (6)	0.0268 (18)
H19	0.3157	0.7145	0.2513	0.032*
C20	0.3878 (10)	0.9637 (4)	0.4003 (8)	0.046 (2)
H20A	0.3831	0.9461	0.4626	0.069*
H20B	0.3735	1.0062	0.4036	0.069*
H20C	0.4736	0.9562	0.3813	0.069*
C21	0.0001 (9)	0.8934 (5)	0.2118 (8)	0.048 (3)
H21A	−0.0350	0.8535	0.2127	0.072*
H21B	−0.0578	0.9177	0.1678	0.072*
H21C	0.0069	0.9104	0.2755	0.072*
C22	0.1435 (11)	0.7132 (4)	0.1049 (7)	0.044 (2)
H22A	0.2338	0.7025	0.1002	0.066*
H22B	0.0910	0.7078	0.0431	0.066*
H22C	0.1097	0.6880	0.1519	0.066*
C23	0.4810 (8)	0.5218 (3)	0.3543 (6)	0.0260 (17)
H23A	0.5089	0.4972	0.4098	0.031*
H23B	0.5581	0.5311	0.3243	0.031*
C24	0.3854 (8)	0.4861 (3)	0.2838 (6)	0.0255 (17)
C25	0.3068 (8)	0.5124 (4)	0.2070 (6)	0.0305 (19)
H25	0.3068	0.5552	0.2000	0.037*
C26	0.2280 (8)	0.4778 (4)	0.1399 (6)	0.0286 (18)
C27	0.2328 (8)	0.4150 (3)	0.1484 (6)	0.0236 (16)
C28	0.3102 (8)	0.3891 (3)	0.2263 (6)	0.0260 (17)
C29	0.3857 (8)	0.4238 (3)	0.2952 (6)	0.0271 (18)
H29	0.4375	0.4053	0.3498	0.032*
C30	0.1251 (10)	0.5617 (4)	0.0575 (7)	0.040 (2)
H30A	0.0973	0.5749	0.1172	0.060*
H30B	0.0568	0.5704	0.0050	0.060*
H30C	0.2050	0.5823	0.0474	0.060*
C31	0.2184 (11)	0.3585 (5)	0.0078 (7)	0.052 (3)
H31A	0.2615	0.3914	−0.0198	0.078*
H31B	0.1557	0.3403	−0.0411	0.078*
H31C	0.2834	0.3294	0.0328	0.078*
C32	0.3822 (11)	0.2990 (4)	0.3112 (6)	0.043 (2)
H32A	0.4705	0.3150	0.3191	0.065*
H32B	0.3853	0.2566	0.2997	0.065*
H32C	0.3424	0.3062	0.3688	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.0183 (3)	0.0261 (3)	0.0220 (3)	0.0008 (3)	0.0004 (2)	0.0002 (3)
Cl1	0.0282 (10)	0.0334 (10)	0.0226 (9)	−0.0008 (8)	−0.0007 (8)	−0.0002 (8)
O1	0.042 (4)	0.026 (3)	0.048 (4)	0.004 (3)	0.001 (3)	−0.004 (3)
O2	0.026 (3)	0.034 (3)	0.035 (3)	0.011 (2)	0.004 (3)	0.007 (3)
O3	0.034 (3)	0.028 (3)	0.037 (4)	0.001 (2)	−0.002 (3)	0.003 (3)
O4	0.040 (4)	0.030 (3)	0.035 (3)	0.008 (3)	−0.010 (3)	0.003 (3)
O5	0.032 (3)	0.027 (3)	0.033 (3)	−0.002 (2)	0.002 (3)	−0.007 (2)
O6	0.031 (3)	0.025 (3)	0.044 (4)	−0.001 (2)	0.007 (3)	0.000 (3)
N1	0.020 (4)	0.026 (3)	0.030 (4)	−0.003 (3)	0.005 (3)	−0.002 (3)
N2	0.022 (4)	0.025 (3)	0.030 (4)	0.006 (3)	0.008 (3)	0.002 (3)
C1	0.027 (5)	0.033 (4)	0.033 (5)	−0.001 (3)	0.008 (4)	0.000 (4)
C2	0.025 (4)	0.046 (5)	0.029 (4)	−0.006 (4)	0.002 (4)	0.000 (4)
C3	0.027 (5)	0.038 (5)	0.031 (5)	0.011 (4)	0.013 (4)	0.005 (4)
C4	0.017 (4)	0.029 (4)	0.013 (3)	0.003 (3)	−0.005 (3)	0.005 (3)
C5	0.016 (4)	0.047 (5)	0.023 (4)	−0.009 (4)	0.001 (3)	−0.005 (4)
C6	0.028 (5)	0.081 (8)	0.045 (6)	−0.029 (5)	−0.009 (4)	−0.018 (5)
C7	0.079 (9)	0.158 (14)	0.039 (6)	−0.101 (10)	0.009 (6)	−0.012 (7)
C8	0.019 (5)	0.065 (6)	0.041 (5)	−0.002 (4)	0.006 (4)	−0.002 (5)
C9	0.024 (5)	0.052 (6)	0.044 (5)	0.004 (4)	0.010 (4)	0.001 (5)
C10	0.062 (8)	0.110 (11)	0.087 (10)	0.066 (8)	0.038 (7)	0.045 (8)
C11	0.060 (7)	0.049 (6)	0.057 (7)	0.031 (5)	0.001 (6)	0.009 (5)
C12	0.037 (5)	0.041 (5)	0.025 (4)	0.002 (4)	−0.004 (4)	0.011 (4)
C13	0.021 (4)	0.030 (4)	0.043 (5)	−0.001 (3)	0.004 (4)	−0.006 (4)
C14	0.031 (5)	0.028 (4)	0.035 (5)	0.003 (4)	0.006 (4)	0.000 (4)
C15	0.019 (4)	0.030 (4)	0.023 (4)	−0.002 (3)	0.002 (3)	−0.007 (3)
C16	0.034 (5)	0.025 (4)	0.040 (5)	−0.004 (3)	0.013 (4)	−0.001 (4)
C17	0.024 (4)	0.031 (4)	0.029 (4)	0.004 (3)	0.010 (4)	0.006 (3)
C18	0.024 (4)	0.026 (4)	0.020 (4)	−0.007 (3)	0.003 (3)	−0.004 (3)
C19	0.019 (4)	0.023 (4)	0.039 (5)	0.000 (3)	0.005 (4)	0.001 (3)
C20	0.042 (6)	0.040 (5)	0.057 (6)	0.000 (4)	0.011 (5)	−0.007 (5)
C21	0.018 (5)	0.058 (6)	0.070 (7)	0.011 (4)	0.012 (5)	0.016 (5)
C22	0.053 (6)	0.027 (4)	0.051 (6)	−0.005 (4)	−0.004 (5)	−0.002 (4)
C23	0.019 (4)	0.031 (4)	0.028 (4)	0.005 (3)	0.001 (3)	0.002 (3)
C24	0.017 (4)	0.029 (4)	0.031 (4)	−0.006 (3)	0.005 (3)	−0.003 (3)
C25	0.028 (5)	0.024 (4)	0.040 (5)	0.006 (3)	0.008 (4)	0.006 (4)
C26	0.027 (5)	0.030 (4)	0.029 (4)	0.001 (3)	0.002 (4)	−0.001 (3)
C27	0.021 (4)	0.027 (4)	0.022 (4)	−0.002 (3)	0.002 (3)	−0.001 (3)
C28	0.026 (4)	0.025 (4)	0.029 (4)	0.002 (3)	0.008 (4)	−0.001 (3)
C29	0.018 (4)	0.030 (4)	0.032 (4)	0.002 (3)	−0.001 (3)	0.000 (4)
C30	0.048 (6)	0.028 (4)	0.042 (5)	0.010 (4)	−0.004 (5)	0.004 (4)
C31	0.056 (7)	0.068 (7)	0.030 (5)	−0.007 (5)	0.000 (5)	−0.027 (5)
C32	0.070 (7)	0.033 (5)	0.026 (5)	0.006 (5)	0.002 (5)	0.002 (4)

Geometric parameters (Å, º)

Rh1—C4	2.040 (7)	C9—H9	0.9600
Rh1—C5	2.107 (8)	C10—H10A	0.9600
Rh1—C8	2.199 (9)	C10—H10B	0.9600
Rh1—C9	2.193 (9)	C11—H11A	0.9600
Rh1—Cl1	2.400 (2)	C11—H11B	0.9600
Rh1—C12	2.096 (8)	C12—H12	0.9600
O1—C16	1.356 (9)	C13—C14	1.520 (12)
O1—C20	1.432 (12)	C13—H13A	0.9600
O2—C17	1.372 (10)	C13—H13B	0.9600
O2—C21	1.416 (10)	C14—C19	1.381 (12)
O3—C18	1.367 (9)	C14—C15	1.386 (11)
O3—C22	1.449 (10)	C15—C16	1.398 (12)
O4—C26	1.346 (10)	C15—H15	0.9600
O4—C30	1.429 (9)	C16—C17	1.409 (12)
O5—C27	1.381 (9)	C17—C18	1.405 (10)
O5—C31	1.421 (10)	C18—C19	1.378 (11)
O6—C28	1.376 (9)	C19—H19	0.9600
O6—C32	1.430 (11)	C20—H20A	0.9599
N1—C1	1.472 (10)	C20—H20B	0.9599
N1—C4	1.344 (10)	C20—H20C	0.9599
N1—C23	1.476 (10)	C21—H21A	0.9599
N2—C3	1.478 (10)	C21—H21B	0.9599
N2—C4	1.338 (10)	C21—H21C	0.9599
N2—C13	1.473 (10)	C22—H22A	0.9599
C1—C2	1.465 (11)	C22—H22B	0.9599
C2—C3	1.512 (11)	C22—H22C	0.9599
C5—C6	1.525 (12)	C23—C24	1.514 (11)
C5—C12	1.377 (12)	C23—H23A	0.9600
C6—C7	1.444 (14)	C23—H23B	0.9600
C7—C8	1.494 (14)	C24—C25	1.380 (11)
C8—C9	1.364 (13)	C24—C29	1.398 (11)
C9—C10	1.480 (14)	C25—C26	1.384 (12)
C10—C11	1.418 (15)	C25—H25	0.9600
C11—C12	1.507 (13)	C26—C27	1.406 (11)
C1—H1A	0.9600	C27—C28	1.381 (11)
C1—H1B	0.9600	C28—C29	1.384 (11)
C2—H2A	0.9600	C29—H29	0.9600
C2—H2B	0.9600	C30—H30A	0.9599
C3—H3A	0.9600	C30—H30B	0.9599
C3—H3B	0.9600	C30—H30C	0.9599
C5—H5	0.9600	C31—H31A	0.9599
C6—H6A	0.9600	C31—H31B	0.9599
C6—H6B	0.9600	C31—H31C	0.9599
C7—H7A	0.9600	C32—H32A	0.9599
C7—H7B	0.9600	C32—H32B	0.9599
C8—H8	0.9600	C32—H32C	0.9599
C4—Rh1—C5	92.7 (3)	C5—C12—C11	125.4 (9)
C4—Rh1—C8	164.2 (4)	C5—C12—Rh1	71.3 (5)
C4—Rh1—C9	159.4 (3)	C11—C12—Rh1	111.8 (6)
C4—Rh1—C12	91.0 (3)	C5—C12—H12	117.3
C4—Rh1—Cl1	88.93 (19)	C11—C12—H12	117.3
C5—Rh1—Cl1	161.3 (2)	Rh1—C12—H12	86.8
C8—Rh1—Cl1	92.8 (3)	N2—C13—C14	112.2 (7)
C9—Rh1—C8	36.2 (3)	N2—C13—H13A	109.2
C9—Rh1—Cl1	92.7 (3)	C14—C13—H13A	109.2
C12—Rh1—C5	38.2 (3)	N2—C13—H13B	109.2
C12—Rh1—Cl1	160.4 (3)	C14—C13—H13B	109.2
C12—Rh1—C9	80.7 (4)	H13A—C13—H13B	107.9
C5—Rh1—C9	92.3 (4)	C19—C14—C15	120.9 (8)
C12—Rh1—C8	92.5 (4)	C19—C14—C13	120.0 (7)
C5—Rh1—C8	80.7 (3)	C15—C14—C13	119.0 (8)
C16—O1—C20	115.8 (7)	C14—C15—C16	120.3 (8)
C17—O2—C21	113.1 (6)	C14—C15—H15	119.8
C18—O3—C22	117.5 (7)	C16—C15—H15	119.8
C26—O4—C30	116.9 (7)	O1—C16—C15	125.7 (8)
C27—O5—C31	111.6 (7)	O1—C16—C17	115.6 (8)
C28—O6—C32	117.3 (7)	C15—C16—C17	118.7 (7)
C4—N1—C1	124.6 (6)	O2—C17—C18	120.3 (7)
C4—N1—C23	120.3 (6)	O2—C17—C16	119.9 (7)
C1—N1—C23	115.1 (6)	C18—C17—C16	119.7 (7)
C4—N2—C13	120.0 (7)	O3—C18—C19	124.5 (7)
C4—N2—C3	126.0 (7)	O3—C18—C17	115.0 (7)
C13—N2—C3	113.7 (6)	C19—C18—C17	120.5 (7)
C2—C1—N1	110.1 (7)	C18—C19—C14	119.8 (7)
C2—C1—H1A	109.6	C18—C19—H19	120.1
N1—C1—H1A	109.6	C14—C19—H19	120.1
C2—C1—H1B	109.6	O1—C20—H20A	109.5
N1—C1—H1B	109.6	O1—C20—H20B	109.5
H1A—C1—H1B	108.2	H20A—C20—H20B	109.5
C1—C2—C3	111.1 (7)	O1—C20—H20C	109.5
C1—C2—H2A	109.4	H20A—C20—H20C	109.5
C3—C2—H2A	109.4	H20B—C20—H20C	109.5
C1—C2—H2B	109.4	O2—C21—H21A	109.5
C3—C2—H2B	109.4	O2—C21—H21B	109.5
H2A—C2—H2B	108.0	H21A—C21—H21B	109.5
N2—C3—C2	110.1 (7)	O2—C21—H21C	109.5
N2—C3—H3A	109.6	H21A—C21—H21C	109.5
C2—C3—H3A	109.6	H21B—C21—H21C	109.5
N2—C3—H3B	109.6	O3—C22—H22A	109.5
C2—C3—H3B	109.6	O3—C22—H22B	109.5
H3A—C3—H3B	108.2	H22A—C22—H22B	109.5
N2—C4—N1	116.1 (7)	O3—C22—H22C	109.5
N2—C4—Rh1	124.0 (6)	H22A—C22—H22C	109.5
N1—C4—Rh1	119.8 (6)	H22B—C22—H22C	109.5
C12—C5—C6	126.2 (9)	N1—C23—C24	114.1 (6)
C12—C5—Rh1	70.5 (5)	N1—C23—H23A	108.7
C6—C5—Rh1	112.4 (6)	C24—C23—H23A	108.7
C12—C5—H5	116.9	N1—C23—H23B	108.7
C6—C5—H5	116.9	C24—C23—H23B	108.7
Rh1—C5—H5	87.0	H23A—C23—H23B	107.6
C7—C6—C5	116.0 (8)	C25—C24—C29	120.1 (7)
C7—C6—H6A	108.3	C25—C24—C23	122.6 (7)
C5—C6—H6A	108.3	C29—C24—C23	117.1 (7)
C7—C6—H6B	108.3	C24—C25—C26	120.9 (7)
C5—C6—H6B	108.3	C24—C25—H25	119.5
H6A—C6—H6B	107.4	C26—C25—H25	119.5
C6—C7—C8	116.8 (8)	O4—C26—C25	125.9 (7)
C6—C7—H7A	108.1	O4—C26—C27	114.9 (7)
C8—C7—H7A	108.1	C25—C26—C27	119.1 (7)
C6—C7—H7B	108.1	O5—C27—C28	120.5 (7)
C8—C7—H7B	108.1	O5—C27—C26	119.7 (7)
H7A—C7—H7B	107.3	C28—C27—C26	119.5 (7)
C9—C8—C7	123.3 (11)	O6—C28—C27	115.5 (7)
C9—C8—Rh1	71.7 (6)	O6—C28—C29	123.2 (7)
C7—C8—Rh1	110.9 (7)	C27—C28—C29	121.3 (7)
C9—C8—H8	118.3	C28—C29—C24	118.9 (7)
C7—C8—H8	118.3	C28—C29—H29	120.5
Rh1—C8—H8	87.4	C24—C29—H29	120.5
C8—C9—C10	126.6 (12)	O4—C30—H30A	109.5
C8—C9—Rh1	72.1 (6)	O4—C30—H30B	109.5
C10—C9—Rh1	109.9 (7)	H30A—C30—H30B	109.5
C8—C9—H9	116.7	O4—C30—H30C	109.5
C10—C9—H9	116.7	H30A—C30—H30C	109.5
Rh1—C9—H9	87.8	H30B—C30—H30C	109.5
C11—C10—C9	116.9 (9)	O5—C31—H31A	109.5
C11—C10—H10A	108.1	O5—C31—H31B	109.5
C9—C10—H10A	108.1	H31A—C31—H31B	109.5
C11—C10—H10B	108.1	O5—C31—H31C	109.5
C9—C10—H10B	108.1	H31A—C31—H31C	109.5
H10A—C10—H10B	107.3	H31B—C31—H31C	109.5
C10—C11—C12	117.2 (9)	O6—C32—H32A	109.5
C10—C11—H11A	108.0	O6—C32—H32B	109.5
C12—C11—H11A	108.0	H32A—C32—H32B	109.5
C10—C11—H11B	108.0	O6—C32—H32C	109.5
C12—C11—H11B	108.0	H32A—C32—H32C	109.5
H11A—C11—H11B	107.3	H32B—C32—H32C	109.5