The structure of a new polymorph of the title compound, [Rh(C8H12)(C7H16N2)]CF3SO3, the first form of which we recently reported [Rouzaud et al. (2003). Helv. Chim. Acta, 86, 1753–1759], has been determined at 180 K in space group C2221. The differences between the two polymorphs are related to the way the individual ions close-pack within the unit cell.
Supporting information
CCDC reference: 227736
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.017 Å
- R factor = 0.041
- wR factor = 0.101
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level A
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5262
| Author Response: The crystal (the largest available from several batches) was
a very thin plate (minimum dimension 0.02 mm) and diffracted weakly
at high angles. Applying a cut-off at 2/q = 21.96 /%resolution
results in a good number of relections observed at the 2/s level and
a good merging R value.
Collection of higher-angle data is only likely to be possible using a
synchrotron or a rotating-anode source. Given the good quality of the
structure refinement using this data set, efforts in this direction are
not warranted.
|
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 21.96 Deg.
| Author Response: Please, see our response to _vrf_THETM01.
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low .............. 21.96 Deg.
| Author Response: Please, see our response to _vrf_THETM01.
|
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
| Author Response: Please, see our response to _vrf_THETM01.
|
Alert level C
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
non-centrosymmetric structure, where ZMAX > 18
sine(theta)/lambda 0.5262
Proportion of unique data used 1.0000
Ratio reflections to parameters 9.2552
| Author Response: Please, see our response to _vrf_THETM01.
|
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C7
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C10
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Rh1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... S1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C16
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.65
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 17
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C8 - C15 = 1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C11 - C12 = 1.35 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 21.96
From the CIF: _reflns_number_total 2212
Count of symmetry unique reflns 1357
Completeness (_total/calc) 163.01%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 855
Fraction of Friedel pairs measured 0.630
Are heavy atom types Z>Si present yes
3 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
1 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
6 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[(
S)-(-)-2-aminomethyl-1-ethylpyrrolidine-
κ2N,
N'](1,5-cyclooctadiene)rhodium(I)
trifluoromethanesulfonate
top
Crystal data top
[Rh(C8H12)(C7H16N2)]CF3SO3 | F(000) = 2000 |
Mr = 488.37 | Dx = 1.650 Mg m−3 |
Orthorhombic, C2221 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2c 2 | Cell parameters from 53723 reflections |
a = 11.7449 (5) Å | θ = 1.0–22.0° |
b = 14.5747 (7) Å | µ = 1.02 mm−1 |
c = 22.9700 (12) Å | T = 180 K |
V = 3932.0 (3) Å3 | Plate, yellow |
Z = 8 | 0.10 × 0.10 × 0.02 mm |
Data collection top
Nonius KappaCCD diffractometer | 2004 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Thin–slice ω and φ scans | θmax = 22.0°, θmin = 3.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −12→12 |
Tmin = 0.899, Tmax = 0.980 | k = −15→15 |
6274 measured reflections | l = −24→24 |
2212 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0477P)2 + 8.7148P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.52 e Å−3 |
2212 reflections | Δρmin = −0.38 e Å−3 |
239 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
16 restraints | Extinction coefficient: 0.0014 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 878 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.06 (8) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Rh1 | 0.14464 (5) | 0.76174 (4) | 0.39523 (2) | 0.0397 (3) | |
N1 | 0.1038 (6) | 0.6159 (5) | 0.3878 (3) | 0.0528 (18) | |
N2 | 0.2723 (6) | 0.7089 (5) | 0.4508 (3) | 0.055 (2) | |
H2A | 0.3410 | 0.7356 | 0.4418 | 0.066* | |
H2D | 0.2550 | 0.7234 | 0.4888 | 0.066* | |
C1 | −0.0848 (10) | 0.6185 (9) | 0.4376 (5) | 0.079 (3) | |
H1A | −0.1272 | 0.5930 | 0.4706 | 0.119* | |
H1B | −0.1232 | 0.6021 | 0.4012 | 0.119* | |
H1C | −0.0814 | 0.6855 | 0.4412 | 0.119* | |
C2 | 0.0308 (11) | 0.5812 (8) | 0.4374 (4) | 0.070 (4) | |
H2B | 0.0263 | 0.5135 | 0.4350 | 0.084* | |
H2C | 0.0682 | 0.5970 | 0.4746 | 0.084* | |
C3 | 0.0627 (11) | 0.5819 (8) | 0.3312 (4) | 0.073 (3) | |
H3A | 0.0039 | 0.6234 | 0.3151 | 0.088* | |
H3B | 0.0297 | 0.5197 | 0.3353 | 0.088* | |
C4 | 0.1680 (12) | 0.5795 (8) | 0.2914 (5) | 0.086 (4) | |
H4A | 0.1734 | 0.5198 | 0.2711 | 0.103* | |
H4B | 0.1640 | 0.6290 | 0.2620 | 0.103* | |
C5 | 0.2681 (10) | 0.5933 (10) | 0.3308 (5) | 0.084 (4) | |
H5A | 0.2964 | 0.6572 | 0.3284 | 0.100* | |
H5B | 0.3308 | 0.5509 | 0.3205 | 0.100* | |
C6 | 0.2219 (8) | 0.5723 (7) | 0.3921 (5) | 0.064 (3) | |
H6A | 0.2125 | 0.5044 | 0.3960 | 0.076* | |
C7 | 0.2820 (11) | 0.6071 (9) | 0.4447 (5) | 0.089 (4) | |
H7A | 0.2495 | 0.5775 | 0.4798 | 0.107* | |
H7B | 0.3634 | 0.5900 | 0.4424 | 0.107* | |
C8 | −0.0095 (8) | 0.8101 (8) | 0.3559 (4) | 0.066 (3) | |
H8A | −0.0689 | 0.7622 | 0.3489 | 0.079* | |
C9 | −0.0489 (10) | 0.8919 (11) | 0.3879 (6) | 0.110 (5) | |
H9A | −0.0734 | 0.9380 | 0.3588 | 0.132* | |
H9B | −0.1174 | 0.8742 | 0.4103 | 0.132* | |
C10 | 0.0291 (13) | 0.9366 (10) | 0.4275 (7) | 0.110 (5) | |
H10A | −0.0079 | 0.9404 | 0.4661 | 0.132* | |
H10B | 0.0414 | 1.0001 | 0.4137 | 0.132* | |
C11 | 0.1423 (10) | 0.8925 (6) | 0.4351 (4) | 0.068 (3) | |
H11A | 0.1706 | 0.8928 | 0.4761 | 0.082* | |
C12 | 0.2257 (9) | 0.8929 (7) | 0.3946 (5) | 0.074 (3) | |
H12A | 0.3040 | 0.8922 | 0.4116 | 0.089* | |
C13 | 0.2200 (12) | 0.9368 (9) | 0.3353 (5) | 0.094 (4) | |
H13A | 0.2019 | 1.0027 | 0.3404 | 0.112* | |
H13B | 0.2965 | 0.9330 | 0.3173 | 0.112* | |
C14 | 0.1383 (13) | 0.8979 (8) | 0.2951 (4) | 0.090 (4) | |
H14A | 0.1784 | 0.8828 | 0.2584 | 0.108* | |
H14B | 0.0808 | 0.9454 | 0.2859 | 0.108* | |
C15 | 0.0766 (8) | 0.8125 (7) | 0.3160 (3) | 0.063 (3) | |
H15A | 0.0693 | 0.7643 | 0.2853 | 0.076* | |
S1 | 0.09178 (19) | 0.2659 (2) | 0.40822 (9) | 0.0609 (7) | |
O1 | 0.0007 (9) | 0.3222 (11) | 0.4121 (5) | 0.192 (7) | |
O2 | 0.1910 (6) | 0.3068 (8) | 0.4301 (3) | 0.132 (5) | |
O3 | 0.0708 (15) | 0.1808 (8) | 0.4283 (4) | 0.216 (8) | |
C16 | 0.1166 (10) | 0.2547 (9) | 0.3321 (4) | 0.090 (3) | |
F1 | 0.1243 (14) | 0.3299 (8) | 0.3079 (4) | 0.212 (6) | |
F2 | 0.2096 (9) | 0.2136 (10) | 0.3201 (5) | 0.217 (7) | |
F3 | 0.0398 (10) | 0.2059 (9) | 0.3090 (3) | 0.204 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Rh1 | 0.0389 (4) | 0.0468 (4) | 0.0334 (3) | 0.0075 (3) | −0.0014 (3) | 0.0022 (3) |
N1 | 0.062 (5) | 0.061 (5) | 0.036 (4) | 0.003 (4) | −0.003 (3) | −0.005 (4) |
N2 | 0.053 (5) | 0.069 (6) | 0.042 (4) | 0.005 (4) | 0.001 (3) | 0.007 (3) |
C1 | 0.074 (8) | 0.083 (9) | 0.081 (7) | 0.001 (6) | 0.026 (6) | 0.008 (6) |
C2 | 0.109 (10) | 0.052 (7) | 0.050 (6) | −0.022 (7) | 0.005 (6) | 0.006 (5) |
C3 | 0.101 (9) | 0.055 (7) | 0.062 (6) | −0.008 (6) | 0.001 (6) | −0.006 (5) |
C4 | 0.116 (11) | 0.078 (8) | 0.064 (7) | 0.019 (7) | 0.006 (8) | −0.011 (5) |
C5 | 0.079 (9) | 0.093 (10) | 0.079 (8) | 0.040 (7) | 0.045 (7) | −0.013 (7) |
C6 | 0.061 (6) | 0.059 (6) | 0.072 (7) | 0.032 (5) | 0.003 (7) | 0.007 (6) |
C7 | 0.097 (9) | 0.085 (10) | 0.085 (8) | 0.044 (8) | −0.015 (7) | 0.010 (7) |
C8 | 0.051 (6) | 0.075 (7) | 0.071 (6) | 0.007 (5) | −0.024 (5) | 0.010 (5) |
C9 | 0.072 (8) | 0.135 (12) | 0.123 (11) | 0.061 (8) | −0.003 (8) | −0.030 (10) |
C10 | 0.129 (13) | 0.085 (10) | 0.115 (11) | 0.060 (10) | 0.015 (10) | −0.031 (8) |
C11 | 0.100 (8) | 0.047 (5) | 0.057 (6) | 0.011 (7) | −0.001 (6) | −0.004 (4) |
C12 | 0.098 (9) | 0.066 (7) | 0.059 (6) | −0.024 (6) | −0.017 (7) | 0.016 (6) |
C13 | 0.126 (12) | 0.085 (9) | 0.071 (7) | −0.040 (8) | −0.012 (8) | 0.025 (6) |
C14 | 0.124 (11) | 0.088 (8) | 0.057 (6) | −0.031 (9) | −0.022 (8) | 0.026 (5) |
C15 | 0.077 (7) | 0.082 (8) | 0.030 (5) | −0.001 (6) | 0.001 (5) | −0.001 (5) |
S1 | 0.0527 (12) | 0.0792 (19) | 0.0509 (13) | −0.0093 (13) | 0.0065 (10) | −0.0078 (13) |
O1 | 0.118 (8) | 0.301 (19) | 0.156 (10) | 0.077 (10) | 0.023 (8) | −0.063 (11) |
O2 | 0.076 (6) | 0.249 (14) | 0.072 (5) | −0.064 (7) | −0.002 (4) | −0.003 (6) |
O3 | 0.43 (2) | 0.138 (11) | 0.084 (6) | −0.126 (14) | 0.021 (10) | 0.023 (7) |
C16 | 0.114 (9) | 0.102 (9) | 0.056 (6) | −0.002 (9) | −0.017 (6) | −0.021 (7) |
F1 | 0.388 (19) | 0.156 (9) | 0.091 (6) | −0.009 (13) | 0.035 (10) | 0.060 (6) |
F2 | 0.168 (9) | 0.322 (19) | 0.161 (9) | 0.054 (10) | 0.065 (7) | −0.111 (11) |
F3 | 0.245 (12) | 0.304 (17) | 0.062 (5) | −0.140 (12) | −0.032 (6) | −0.019 (6) |
Geometric parameters (Å, º) top
Rh1—C11 | 2.115 (9) | C7—H7A | 0.990 |
Rh1—N2 | 2.114 (6) | C7—H7B | 0.990 |
Rh1—C15 | 2.121 (9) | C8—C15 | 1.365 (8) |
Rh1—C12 | 2.135 (10) | C8—C9 | 1.474 (15) |
Rh1—C8 | 2.143 (9) | C8—H8A | 1.000 |
Rh1—N1 | 2.186 (7) | C9—C10 | 1.446 (14) |
N1—C3 | 1.473 (12) | C9—H9A | 0.990 |
N1—C2 | 1.512 (12) | C9—H9B | 0.990 |
N1—C6 | 1.529 (11) | C10—C11 | 1.486 (16) |
N2—C7 | 1.494 (14) | C10—H10A | 0.990 |
N2—H2A | 0.920 | C10—H10B | 0.990 |
N2—H2D | 0.920 | C11—C12 | 1.351 (9) |
C1—C2 | 1.462 (16) | C11—H11A | 1.000 |
C1—H1A | 0.980 | C12—C13 | 1.507 (15) |
C1—H1B | 0.980 | C12—H12A | 1.000 |
C1—H1C | 0.980 | C13—C14 | 1.448 (12) |
C2—H2B | 0.990 | C13—H13A | 0.990 |
C2—H2C | 0.990 | C13—H13B | 0.990 |
C3—C4 | 1.537 (16) | C14—C15 | 1.519 (14) |
C3—H3A | 0.990 | C14—H14A | 0.990 |
C3—H3B | 0.990 | C14—H14B | 0.990 |
C4—C5 | 1.497 (15) | C15—H15A | 1.000 |
C4—H4A | 0.990 | S1—O1 | 1.351 (10) |
C4—H4B | 0.990 | S1—O3 | 1.346 (10) |
C5—C6 | 1.540 (15) | S1—O2 | 1.402 (7) |
C5—H5A | 0.990 | S1—C16 | 1.780 (10) |
C5—H5B | 0.990 | C16—F1 | 1.232 (13) |
C6—C7 | 1.490 (15) | C16—F3 | 1.266 (11) |
C6—H6A | 1.000 | C16—F2 | 1.276 (13) |
| | | |
C11—Rh1—N2 | 94.4 (3) | C6—C7—H7A | 109.2 |
C11—Rh1—C15 | 93.0 (4) | N2—C7—H7B | 109.2 |
N2—Rh1—C15 | 155.8 (3) | C6—C7—H7B | 109.2 |
C11—Rh1—C12 | 37.1 (3) | H7A—C7—H7B | 107.9 |
N2—Rh1—C12 | 90.8 (4) | C15—C8—C9 | 123.1 (11) |
C15—Rh1—C12 | 81.4 (4) | C15—C8—Rh1 | 70.5 (5) |
C11—Rh1—C8 | 82.8 (4) | C9—C8—Rh1 | 108.7 (7) |
N2—Rh1—C8 | 166.8 (3) | C15—C8—H8A | 115.2 |
C15—Rh1—C8 | 37.3 (2) | C9—C8—H8A | 115.2 |
C12—Rh1—C8 | 94.5 (4) | Rh1—C8—H8A | 115.2 |
C11—Rh1—N1 | 155.1 (3) | C10—C9—C8 | 118.6 (9) |
N2—Rh1—N1 | 81.3 (3) | C10—C9—H9A | 107.7 |
C15—Rh1—N1 | 100.9 (3) | C8—C9—H9A | 107.7 |
C12—Rh1—N1 | 165.4 (3) | C10—C9—H9B | 107.7 |
C8—Rh1—N1 | 95.8 (4) | C8—C9—H9B | 107.7 |
C3—N1—C2 | 111.5 (8) | H9A—C9—H9B | 107.1 |
C3—N1—C6 | 102.3 (8) | C9—C10—C11 | 116.5 (10) |
C2—N1—C6 | 109.1 (8) | C9—C10—H10A | 108.2 |
C3—N1—Rh1 | 117.9 (6) | C11—C10—H10A | 108.2 |
C2—N1—Rh1 | 113.0 (6) | C9—C10—H10B | 108.2 |
C6—N1—Rh1 | 101.5 (5) | C11—C10—H10B | 108.2 |
C7—N2—Rh1 | 111.1 (6) | H10A—C10—H10B | 107.3 |
C7—N2—H2A | 109.4 | C12—C11—C10 | 124.5 (10) |
Rh1—N2—H2A | 109.4 | C12—C11—Rh1 | 72.3 (5) |
C7—N2—H2D | 109.4 | C10—C11—Rh1 | 110.5 (8) |
Rh1—N2—H2D | 109.4 | C12—C11—H11A | 114.0 |
H2A—N2—H2D | 108.0 | C10—C11—H11A | 114.0 |
C2—C1—H1A | 109.5 | Rh1—C11—H11A | 114.0 |
C2—C1—H1B | 109.5 | C11—C12—C13 | 126.3 (11) |
H1A—C1—H1B | 109.5 | C11—C12—Rh1 | 70.6 (5) |
C2—C1—H1C | 109.5 | C13—C12—Rh1 | 111.5 (8) |
H1A—C1—H1C | 109.5 | C11—C12—H12A | 113.5 |
H1B—C1—H1C | 109.5 | C13—C12—H12A | 113.5 |
C1—C2—N1 | 113.9 (9) | Rh1—C12—H12A | 113.5 |
C1—C2—H2B | 108.8 | C14—C13—C12 | 116.1 (9) |
N1—C2—H2B | 108.8 | C14—C13—H13A | 108.3 |
C1—C2—H2C | 108.8 | C12—C13—H13A | 108.3 |
N1—C2—H2C | 108.8 | C14—C13—H13B | 108.3 |
H2B—C2—H2C | 107.7 | C12—C13—H13B | 108.3 |
N1—C3—C4 | 105.6 (9) | H13A—C13—H13B | 107.4 |
N1—C3—H3A | 110.6 | C13—C14—C15 | 115.8 (8) |
C4—C3—H3A | 110.6 | C13—C14—H14A | 108.3 |
N1—C3—H3B | 110.6 | C15—C14—H14A | 108.3 |
C4—C3—H3B | 110.6 | C13—C14—H14B | 108.3 |
H3A—C3—H3B | 108.8 | C15—C14—H14B | 108.3 |
C5—C4—C3 | 105.7 (8) | H14A—C14—H14B | 107.4 |
C5—C4—H4A | 110.6 | C8—C15—C14 | 125.9 (11) |
C3—C4—H4A | 110.6 | C8—C15—Rh1 | 72.2 (5) |
C5—C4—H4B | 110.6 | C14—C15—Rh1 | 112.2 (7) |
C3—C4—H4B | 110.6 | C8—C15—H15A | 113.1 |
H4A—C4—H4B | 108.7 | C14—C15—H15A | 113.1 |
C4—C5—C6 | 104.4 (10) | Rh1—C15—H15A | 113.1 |
C4—C5—H5A | 110.9 | O1—S1—O3 | 113.0 (9) |
C6—C5—H5A | 110.9 | O1—S1—O2 | 112.1 (8) |
C4—C5—H5B | 110.9 | O3—S1—O2 | 114.9 (8) |
C6—C5—H5B | 110.9 | O1—S1—C16 | 104.5 (7) |
H5A—C5—H5B | 108.9 | O3—S1—C16 | 106.4 (7) |
C7—C6—N1 | 109.9 (8) | O2—S1—C16 | 104.7 (5) |
C7—C6—C5 | 120.5 (11) | F1—C16—F3 | 111.3 (12) |
N1—C6—C5 | 100.3 (8) | F1—C16—F2 | 105.0 (12) |
C7—C6—H6A | 108.5 | F3—C16—F2 | 104.8 (11) |
N1—C6—H6A | 108.5 | F1—C16—S1 | 111.9 (9) |
C5—C6—H6A | 108.5 | F3—C16—S1 | 110.3 (9) |
N2—C7—C6 | 112.2 (8) | F2—C16—S1 | 113.3 (9) |
N2—C7—H7A | 109.2 | | |
| | | |
C11—Rh1—N1—C3 | 133.7 (10) | C8—C9—C10—C11 | −3 (2) |
N2—Rh1—N1—C3 | −144.7 (7) | C9—C10—C11—C12 | 72.3 (18) |
C15—Rh1—N1—C3 | 10.8 (8) | C9—C10—C11—Rh1 | −9.8 (17) |
C12—Rh1—N1—C3 | −87.0 (15) | N2—Rh1—C11—C12 | 85.5 (6) |
C8—Rh1—N1—C3 | 48.2 (7) | C15—Rh1—C11—C12 | −71.5 (7) |
C11—Rh1—N1—C2 | 1.2 (11) | C8—Rh1—C11—C12 | −107.4 (7) |
N2—Rh1—N1—C2 | 82.7 (7) | N1—Rh1—C11—C12 | 164.2 (7) |
C15—Rh1—N1—C2 | −121.7 (7) | N2—Rh1—C11—C10 | −153.5 (9) |
C12—Rh1—N1—C2 | 140.5 (14) | C15—Rh1—C11—C10 | 49.5 (9) |
C8—Rh1—N1—C2 | −84.3 (7) | C12—Rh1—C11—C10 | 121.0 (11) |
C11—Rh1—N1—C6 | −115.5 (9) | C8—Rh1—C11—C10 | 13.6 (9) |
N2—Rh1—N1—C6 | −33.9 (6) | N1—Rh1—C11—C10 | −74.8 (12) |
C15—Rh1—N1—C6 | 121.6 (6) | C10—C11—C12—C13 | −0.2 (18) |
C12—Rh1—N1—C6 | 23.8 (18) | Rh1—C11—C12—C13 | 102.9 (11) |
C8—Rh1—N1—C6 | 159.0 (6) | C10—C11—C12—Rh1 | −103.1 (11) |
C11—Rh1—N2—C7 | 167.6 (7) | N2—Rh1—C12—C11 | −96.2 (6) |
C15—Rh1—N2—C7 | −85.1 (11) | C15—Rh1—C12—C11 | 106.7 (7) |
C12—Rh1—N2—C7 | −155.5 (7) | C8—Rh1—C12—C11 | 71.7 (7) |
C8—Rh1—N2—C7 | 90.5 (18) | N1—Rh1—C12—C11 | −152.9 (12) |
N1—Rh1—N2—C7 | 12.2 (7) | C11—Rh1—C12—C13 | −122.4 (12) |
C3—N1—C2—C1 | −67.7 (12) | N2—Rh1—C12—C13 | 141.4 (9) |
C6—N1—C2—C1 | −179.9 (9) | C15—Rh1—C12—C13 | −15.7 (9) |
Rh1—N1—C2—C1 | 67.9 (10) | C8—Rh1—C12—C13 | −50.7 (9) |
C2—N1—C3—C4 | −152.8 (9) | N1—Rh1—C12—C13 | 84.6 (17) |
C6—N1—C3—C4 | −36.4 (10) | C11—C12—C13—C14 | −65.2 (18) |
Rh1—N1—C3—C4 | 74.0 (10) | Rh1—C12—C13—C14 | 16.0 (16) |
N1—C3—C4—C5 | 11.8 (11) | C12—C13—C14—C15 | −5.3 (19) |
C3—C4—C5—C6 | 17.5 (11) | C9—C8—C15—C14 | −4.8 (15) |
C3—N1—C6—C7 | 174.3 (9) | Rh1—C8—C15—C14 | −104.9 (10) |
C2—N1—C6—C7 | −67.5 (10) | C9—C8—C15—Rh1 | 100.1 (10) |
Rh1—N1—C6—C7 | 52.0 (9) | C13—C14—C15—C8 | 75.5 (17) |
C3—N1—C6—C5 | 46.4 (10) | C13—C14—C15—Rh1 | −8.1 (15) |
C2—N1—C6—C5 | 164.6 (9) | C11—Rh1—C15—C8 | −74.0 (7) |
Rh1—N1—C6—C5 | −75.9 (8) | N2—Rh1—C15—C8 | 178.3 (8) |
C4—C5—C6—C7 | −159.6 (10) | C12—Rh1—C15—C8 | −109.3 (7) |
C4—C5—C6—N1 | −39.0 (10) | N1—Rh1—C15—C8 | 85.3 (7) |
Rh1—N2—C7—C6 | 14.1 (12) | C11—Rh1—C15—C14 | 48.3 (9) |
N1—C6—C7—N2 | −46.0 (13) | N2—Rh1—C15—C14 | −59.3 (13) |
C5—C6—C7—N2 | 69.6 (12) | C12—Rh1—C15—C14 | 13.0 (8) |
C11—Rh1—C8—C15 | 104.6 (7) | C8—Rh1—C15—C14 | 122.3 (11) |
N2—Rh1—C8—C15 | −177.0 (14) | N1—Rh1—C15—C14 | −152.4 (8) |
C12—Rh1—C8—C15 | 69.4 (7) | O1—S1—C16—F1 | 52.6 (14) |
N1—Rh1—C8—C15 | −100.4 (6) | O3—S1—C16—F1 | 172.4 (13) |
C11—Rh1—C8—C9 | −14.9 (9) | O2—S1—C16—F1 | −65.5 (13) |
N2—Rh1—C8—C9 | 64 (2) | O1—S1—C16—F3 | −71.9 (13) |
C15—Rh1—C8—C9 | −119.5 (12) | O3—S1—C16—F3 | 48.0 (13) |
C12—Rh1—C8—C9 | −50.1 (9) | O2—S1—C16—F3 | 170.0 (11) |
N1—Rh1—C8—C9 | 140.2 (8) | O1—S1—C16—F2 | 171.0 (12) |
C15—C8—C9—C10 | −64.3 (18) | O3—S1—C16—F2 | −69.2 (13) |
Rh1—C8—C9—C10 | 14.2 (17) | O2—S1—C16—F2 | 52.9 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.92 | 2.36 | 3.273 (16) | 171 |
N2—H2D···O2ii | 0.92 | 2.06 | 2.908 (10) | 153 |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, −y+1, −z+1. |