In the title compound, [Ir(C8H12)(C8H14N2)(C18H15P)]BF4, the cationic complex has the anticipated square-planar geometry. The asymmetric unit comprises the iridium complex and one tetrafluoridoborate anion. The space group is non-centrosymmetric, with the Flack parameter of 0.007 (3) well determined, and confirms the hand for the complex cation. This compound shows promising catalytic activity in transfer hydrogenation reactions.
Supporting information
CCDC reference: 1577406
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.015
- wR factor = 0.033
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28 .. F3 .. 2.58 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. F4 .. 2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. F3 .. 2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. F2 .. 2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. F2 .. 2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. F4 .. 2.56 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 66 %
Alert level G
PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of B1 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
2 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: Olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
[(1,2,5,6-
η)-Cycloocta-1,5-diene](1-ethyl-3-isopropyl-1,3-imidazol-2-ylidene-
κC2)(triphenylphosphane-
κP)iridium(I)
tetrafluoridoborate
top
Crystal data top
C34H41IrN2P+·BF4− | F(000) = 1568 |
Mr = 787.67 | Dx = 1.659 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 17.4915 (13) Å | Cell parameters from 9729 reflections |
b = 10.2653 (8) Å | θ = 2.3–28.3° |
c = 18.644 (2) Å | µ = 4.34 mm−1 |
β = 109.6047 (16)° | T = 150 K |
V = 3153.5 (5) Å3 | Plate, clear orange |
Z = 4 | 0.3 × 0.2 × 0.12 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6410 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 28.3°, θmin = 2.3° |
Tmin = 0.576, Tmax = 0.746 | h = −23→13 |
25634 measured reflections | k = −13→13 |
6517 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.015 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.033 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.81 e Å−3 |
6517 reflections | Δρmin = −0.57 e Å−3 |
391 parameters | Absolute structure: Flack x determined using 2467 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al, 2013) |
2 restraints | Absolute structure parameter: 0.007 (3) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Ir1 | 0.38107 (2) | 0.82129 (2) | 0.58767 (2) | 0.01181 (3) | |
C1 | 0.2700 (4) | 0.8408 (4) | 0.6009 (3) | 0.0148 (11) | |
C13 | 0.4968 (4) | 0.8485 (6) | 0.5689 (4) | 0.0219 (11) | |
H13 | 0.4929 | 0.8445 | 0.5142 | 0.026* | |
C14 | 0.5403 (3) | 0.9684 (4) | 0.6107 (2) | 0.0275 (10) | |
H14A | 0.5199 | 1.0462 | 0.5786 | 0.033* | |
H14B | 0.5990 | 0.9603 | 0.6190 | 0.033* | |
N1 | 0.2213 (2) | 0.9453 (3) | 0.59388 (18) | 0.0161 (7) | |
N2 | 0.22893 (16) | 0.7402 (3) | 0.61841 (16) | 0.0164 (5) | |
C4 | 0.2575 (2) | 0.6041 (3) | 0.6270 (2) | 0.0220 (7) | |
H4A | 0.3089 | 0.5989 | 0.6157 | 0.026* | |
H4B | 0.2169 | 0.5491 | 0.5894 | 0.026* | |
C3 | 0.1544 (2) | 0.7809 (3) | 0.6207 (2) | 0.0204 (7) | |
H3 | 0.1146 | 0.7286 | 0.6312 | 0.024* | |
C12 | 0.49705 (19) | 0.7269 (3) | 0.60237 (19) | 0.0193 (7) | |
H12 | 0.4931 | 0.6521 | 0.5669 | 0.023* | |
C6 | 0.2415 (2) | 1.0805 (3) | 0.57994 (19) | 0.0189 (7) | |
H6 | 0.2945 | 1.0796 | 0.5706 | 0.023* | |
P1 | 0.31715 (7) | 0.77862 (11) | 0.45900 (6) | 0.0133 (2) | |
C9 | 0.4315 (3) | 0.8179 (3) | 0.7132 (3) | 0.0198 (11) | |
H9 | 0.3896 | 0.8169 | 0.7388 | 0.024* | |
C10 | 0.4914 (3) | 0.7073 (4) | 0.7358 (2) | 0.0232 (8) | |
H10A | 0.4615 | 0.6247 | 0.7335 | 0.028* | |
H10B | 0.5271 | 0.7203 | 0.7892 | 0.028* | |
C29 | 0.2240 (3) | 0.6807 (3) | 0.4333 (2) | 0.0163 (7) | |
C23 | 0.3788 (2) | 0.7051 (3) | 0.40747 (19) | 0.0171 (6) | |
C22 | 0.2172 (2) | 0.9413 (3) | 0.34318 (18) | 0.0194 (7) | |
H22 | 0.1847 | 0.8664 | 0.3245 | 0.023* | |
C34 | 0.1553 (2) | 0.7331 (3) | 0.44541 (18) | 0.0184 (7) | |
H34 | 0.1563 | 0.8210 | 0.4617 | 0.022* | |
C18 | 0.3319 (2) | 1.0435 (3) | 0.43574 (19) | 0.0200 (7) | |
H18 | 0.3779 | 1.0383 | 0.4809 | 0.024* | |
C19 | 0.3123 (3) | 1.1609 (3) | 0.3976 (2) | 0.0270 (8) | |
H19 | 0.3449 | 1.2357 | 0.4161 | 0.032* | |
C28 | 0.4147 (2) | 0.5825 (3) | 0.43037 (19) | 0.0215 (7) | |
H28 | 0.4041 | 0.5363 | 0.4702 | 0.026* | |
C17 | 0.28505 (19) | 0.9328 (3) | 0.40866 (18) | 0.0166 (6) | |
C21 | 0.1968 (2) | 1.0597 (3) | 0.3051 (2) | 0.0262 (8) | |
H21 | 0.1502 | 1.0656 | 0.2606 | 0.031* | |
C16 | 0.4456 (2) | 0.9395 (3) | 0.68829 (18) | 0.0193 (7) | |
H16 | 0.4113 | 1.0097 | 0.6990 | 0.023* | |
C30 | 0.2198 (2) | 0.5519 (3) | 0.40753 (19) | 0.0237 (7) | |
H30 | 0.2651 | 0.5144 | 0.3980 | 0.028* | |
C2 | 0.1494 (2) | 0.9095 (3) | 0.6053 (2) | 0.0200 (7) | |
H2 | 0.1052 | 0.9653 | 0.6027 | 0.024* | |
C33 | 0.0858 (2) | 0.6591 (3) | 0.4341 (2) | 0.0247 (8) | |
H33 | 0.0401 | 0.6959 | 0.4432 | 0.030* | |
C32 | 0.0835 (2) | 0.5312 (4) | 0.4095 (2) | 0.0275 (8) | |
H32 | 0.0363 | 0.4799 | 0.4021 | 0.033* | |
C24 | 0.3962 (2) | 0.7705 (3) | 0.3494 (2) | 0.0215 (7) | |
H24 | 0.3727 | 0.8536 | 0.3335 | 0.026* | |
C11 | 0.5439 (2) | 0.6955 (3) | 0.6852 (2) | 0.0249 (8) | |
H11A | 0.5907 | 0.7555 | 0.7040 | 0.030* | |
H11B | 0.5654 | 0.6056 | 0.6886 | 0.030* | |
C20 | 0.2444 (3) | 1.1690 (3) | 0.3321 (2) | 0.0282 (9) | |
H20 | 0.2307 | 1.2496 | 0.3057 | 0.034* | |
C26 | 0.4826 (2) | 0.5959 (4) | 0.3378 (2) | 0.0290 (8) | |
H26 | 0.5183 | 0.5593 | 0.3145 | 0.035* | |
C5 | 0.2714 (2) | 0.5513 (3) | 0.7060 (2) | 0.0276 (8) | |
H5A | 0.2924 | 0.4622 | 0.7094 | 0.041* | |
H5B | 0.2201 | 0.5512 | 0.7163 | 0.041* | |
H5C | 0.3109 | 0.6064 | 0.7435 | 0.041* | |
C27 | 0.4655 (2) | 0.5290 (4) | 0.3950 (2) | 0.0265 (8) | |
H27 | 0.4890 | 0.4457 | 0.4103 | 0.032* | |
C8 | 0.2512 (3) | 1.1643 (3) | 0.6500 (3) | 0.0315 (9) | |
H8A | 0.1988 | 1.1719 | 0.6580 | 0.047* | |
H8B | 0.2704 | 1.2512 | 0.6424 | 0.047* | |
H8C | 0.2907 | 1.1237 | 0.6948 | 0.047* | |
C31 | 0.1498 (2) | 0.4784 (3) | 0.3958 (2) | 0.0295 (8) | |
H31 | 0.1476 | 0.3912 | 0.3783 | 0.035* | |
C15 | 0.5280 (2) | 0.9876 (4) | 0.6880 (2) | 0.0247 (8) | |
H15A | 0.5713 | 0.9404 | 0.7277 | 0.030* | |
H15B | 0.5334 | 1.0814 | 0.7012 | 0.030* | |
C25 | 0.4471 (2) | 0.7169 (4) | 0.3144 (2) | 0.0296 (8) | |
H25 | 0.4579 | 0.7625 | 0.2745 | 0.036* | |
C7 | 0.1775 (2) | 1.1369 (4) | 0.5098 (2) | 0.0303 (8) | |
H7A | 0.1716 | 1.0805 | 0.4659 | 0.045* | |
H7B | 0.1941 | 1.2242 | 0.4997 | 0.045* | |
H7C | 0.1255 | 1.1424 | 0.5188 | 0.045* | |
F3 | 0.46323 (17) | 0.3183 (2) | 0.53320 (17) | 0.0442 (7) | |
F4 | 0.4980 (2) | 0.3779 (4) | 0.6562 (2) | 0.0893 (14) | |
B1 | 0.4349 (3) | 0.3333 (4) | 0.5942 (3) | 0.0272 (9) | |
F1 | 0.3696 (3) | 0.4149 (3) | 0.5731 (3) | 0.0969 (17) | |
F2 | 0.41140 (18) | 0.2160 (3) | 0.61307 (19) | 0.0560 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ir1 | 0.01033 (5) | 0.01332 (5) | 0.01119 (5) | −0.00084 (8) | 0.00286 (3) | −0.00066 (7) |
C1 | 0.016 (3) | 0.0157 (18) | 0.010 (2) | −0.0001 (16) | 0.0005 (18) | −0.0021 (15) |
C13 | 0.009 (2) | 0.036 (2) | 0.022 (3) | 0.000 (2) | 0.0065 (19) | −0.004 (2) |
C14 | 0.0154 (18) | 0.033 (2) | 0.032 (2) | −0.0116 (16) | 0.0040 (18) | −0.0027 (18) |
N1 | 0.0129 (14) | 0.0152 (13) | 0.0190 (16) | −0.0006 (11) | 0.0036 (13) | −0.0018 (12) |
N2 | 0.0157 (13) | 0.0160 (13) | 0.0184 (14) | −0.0017 (11) | 0.0070 (11) | −0.0029 (10) |
C4 | 0.0278 (18) | 0.0119 (14) | 0.0289 (18) | −0.0015 (13) | 0.0131 (15) | −0.0013 (13) |
C3 | 0.0181 (16) | 0.0232 (16) | 0.0236 (17) | −0.0061 (14) | 0.0120 (14) | −0.0045 (14) |
C12 | 0.0126 (15) | 0.0258 (16) | 0.0183 (16) | 0.0042 (13) | 0.0036 (13) | −0.0049 (14) |
C6 | 0.0192 (16) | 0.0154 (15) | 0.0235 (17) | 0.0005 (12) | 0.0088 (14) | −0.0011 (12) |
P1 | 0.0140 (5) | 0.0135 (5) | 0.0117 (4) | 0.0006 (4) | 0.0033 (4) | 0.0000 (4) |
C9 | 0.019 (2) | 0.027 (3) | 0.0121 (18) | 0.0011 (16) | 0.0029 (16) | −0.0018 (15) |
C10 | 0.024 (2) | 0.0253 (17) | 0.0158 (17) | 0.0038 (17) | 0.0011 (16) | 0.0042 (14) |
C29 | 0.0156 (18) | 0.0178 (16) | 0.0142 (16) | −0.0023 (12) | 0.0034 (14) | 0.0018 (12) |
C23 | 0.0153 (16) | 0.0201 (15) | 0.0148 (15) | −0.0015 (12) | 0.0035 (13) | −0.0043 (12) |
C22 | 0.0212 (16) | 0.0210 (16) | 0.0139 (15) | 0.0003 (13) | 0.0031 (13) | −0.0007 (12) |
C34 | 0.0162 (16) | 0.0190 (15) | 0.0177 (16) | −0.0016 (13) | 0.0028 (13) | −0.0009 (12) |
C18 | 0.0201 (16) | 0.0208 (15) | 0.0171 (15) | −0.0021 (13) | 0.0036 (13) | 0.0011 (13) |
C19 | 0.031 (2) | 0.0208 (17) | 0.030 (2) | −0.0049 (14) | 0.0110 (17) | 0.0008 (14) |
C28 | 0.0204 (17) | 0.0221 (16) | 0.0202 (17) | −0.0004 (13) | 0.0043 (14) | −0.0037 (13) |
C17 | 0.0186 (15) | 0.0178 (15) | 0.0145 (15) | 0.0017 (12) | 0.0070 (13) | 0.0021 (12) |
C21 | 0.0293 (19) | 0.0294 (18) | 0.0173 (16) | 0.0044 (15) | 0.0041 (14) | 0.0074 (14) |
C16 | 0.0179 (15) | 0.0213 (16) | 0.0162 (15) | −0.0030 (13) | 0.0022 (13) | −0.0064 (12) |
C30 | 0.0227 (17) | 0.0225 (16) | 0.0245 (17) | −0.0029 (14) | 0.0061 (15) | −0.0048 (14) |
C2 | 0.0133 (14) | 0.0246 (16) | 0.0239 (17) | −0.0006 (13) | 0.0087 (13) | −0.0053 (13) |
C33 | 0.0170 (17) | 0.0339 (19) | 0.0218 (18) | −0.0033 (14) | 0.0045 (15) | −0.0009 (14) |
C32 | 0.0233 (18) | 0.0285 (18) | 0.0285 (19) | −0.0127 (15) | 0.0059 (15) | 0.0004 (15) |
C24 | 0.0227 (17) | 0.0229 (17) | 0.0194 (17) | −0.0026 (14) | 0.0077 (14) | −0.0016 (13) |
C11 | 0.0190 (18) | 0.0278 (18) | 0.0234 (19) | 0.0072 (14) | 0.0013 (15) | 0.0001 (14) |
C20 | 0.036 (2) | 0.0231 (18) | 0.025 (2) | 0.0043 (15) | 0.0107 (18) | 0.0105 (14) |
C26 | 0.0237 (18) | 0.036 (2) | 0.031 (2) | −0.0038 (16) | 0.0133 (16) | −0.0181 (16) |
C5 | 0.033 (2) | 0.0200 (16) | 0.0297 (19) | −0.0013 (15) | 0.0107 (16) | 0.0023 (14) |
C27 | 0.0246 (18) | 0.0244 (17) | 0.0292 (19) | 0.0036 (15) | 0.0073 (15) | −0.0075 (15) |
C8 | 0.036 (2) | 0.0240 (18) | 0.039 (2) | −0.0057 (15) | 0.018 (2) | −0.0114 (15) |
C31 | 0.0302 (19) | 0.0208 (17) | 0.034 (2) | −0.0077 (15) | 0.0057 (16) | −0.0062 (15) |
C15 | 0.0182 (16) | 0.0266 (18) | 0.0251 (18) | −0.0053 (14) | 0.0017 (14) | −0.0041 (14) |
C25 | 0.032 (2) | 0.036 (2) | 0.0244 (19) | −0.0092 (17) | 0.0146 (17) | −0.0064 (16) |
C7 | 0.029 (2) | 0.0283 (18) | 0.034 (2) | 0.0080 (16) | 0.0104 (17) | 0.0092 (16) |
F3 | 0.0328 (15) | 0.0667 (19) | 0.0371 (15) | 0.0054 (11) | 0.0172 (12) | 0.0015 (11) |
F4 | 0.077 (2) | 0.137 (3) | 0.074 (2) | −0.074 (2) | 0.053 (2) | −0.067 (2) |
B1 | 0.028 (2) | 0.0185 (19) | 0.040 (3) | −0.0021 (16) | 0.017 (2) | −0.0008 (16) |
F1 | 0.110 (3) | 0.083 (2) | 0.134 (4) | 0.073 (3) | 0.087 (3) | 0.062 (3) |
F2 | 0.059 (2) | 0.0327 (13) | 0.079 (2) | −0.0114 (13) | 0.0269 (17) | 0.0123 (14) |
Geometric parameters (Å, º) top
Ir1—C1 | 2.049 (7) | C34—H34 | 0.9500 |
Ir1—C12 | 2.181 (3) | C18—C19 | 1.382 (5) |
Ir1—C13 | 2.185 (7) | C18—C17 | 1.394 (4) |
Ir1—C16 | 2.201 (3) | C18—H18 | 0.9500 |
Ir1—C9 | 2.207 (5) | C19—C20 | 1.391 (6) |
Ir1—P1 | 2.3232 (11) | C19—H19 | 0.9500 |
C1—N1 | 1.349 (6) | C28—C27 | 1.385 (5) |
C1—N2 | 1.359 (6) | C28—H28 | 0.9500 |
C13—C12 | 1.395 (7) | C21—C20 | 1.388 (5) |
C13—C14 | 1.517 (7) | C21—H21 | 0.9500 |
C13—H13 | 1.0000 | C16—C15 | 1.526 (5) |
C14—C15 | 1.540 (6) | C16—H16 | 1.0000 |
C14—H14A | 0.9900 | C30—C31 | 1.392 (5) |
C14—H14B | 0.9900 | C30—H30 | 0.9500 |
N1—C2 | 1.393 (5) | C2—H2 | 0.9500 |
N1—C6 | 1.477 (4) | C33—C32 | 1.387 (5) |
N2—C3 | 1.384 (4) | C33—H33 | 0.9500 |
N2—C4 | 1.474 (4) | C32—C31 | 1.378 (5) |
C4—C5 | 1.511 (5) | C32—H32 | 0.9500 |
C4—H4A | 0.9900 | C24—C25 | 1.382 (5) |
C4—H4B | 0.9900 | C24—H24 | 0.9500 |
C3—C2 | 1.348 (5) | C11—H11A | 0.9900 |
C3—H3 | 0.9500 | C11—H11B | 0.9900 |
C12—C11 | 1.520 (5) | C20—H20 | 0.9500 |
C12—H12 | 1.0000 | C26—C27 | 1.383 (5) |
C6—C7 | 1.521 (5) | C26—C25 | 1.391 (6) |
C6—C8 | 1.526 (5) | C26—H26 | 0.9500 |
C6—H6 | 1.0000 | C5—H5A | 0.9800 |
P1—C17 | 1.829 (3) | C5—H5B | 0.9800 |
P1—C23 | 1.830 (4) | C5—H5C | 0.9800 |
P1—C29 | 1.837 (4) | C27—H27 | 0.9500 |
C9—C16 | 1.383 (5) | C8—H8A | 0.9800 |
C9—C10 | 1.507 (6) | C8—H8B | 0.9800 |
C9—H9 | 1.0000 | C8—H8C | 0.9800 |
C10—C11 | 1.526 (6) | C31—H31 | 0.9500 |
C10—H10A | 0.9900 | C15—H15A | 0.9900 |
C10—H10B | 0.9900 | C15—H15B | 0.9900 |
C29—C30 | 1.400 (4) | C25—H25 | 0.9500 |
C29—C34 | 1.402 (5) | C7—H7A | 0.9800 |
C23—C24 | 1.392 (5) | C7—H7B | 0.9800 |
C23—C28 | 1.408 (4) | C7—H7C | 0.9800 |
C22—C17 | 1.391 (4) | F3—B1 | 1.393 (6) |
C22—C21 | 1.392 (5) | F4—B1 | 1.381 (6) |
C22—H22 | 0.9500 | B1—F2 | 1.356 (5) |
C34—C33 | 1.387 (5) | B1—F1 | 1.363 (6) |
| | | |
C1—Ir1—C12 | 155.25 (16) | C19—C18—C17 | 120.7 (3) |
C1—Ir1—C13 | 166.86 (13) | C19—C18—H18 | 119.7 |
C12—Ir1—C13 | 37.26 (17) | C17—C18—H18 | 119.7 |
C1—Ir1—C16 | 94.56 (17) | C18—C19—C20 | 119.7 (3) |
C12—Ir1—C16 | 87.05 (13) | C18—C19—H19 | 120.1 |
C13—Ir1—C16 | 80.12 (19) | C20—C19—H19 | 120.1 |
C1—Ir1—C9 | 86.1 (2) | C27—C28—C23 | 120.2 (3) |
C12—Ir1—C9 | 80.55 (17) | C27—C28—H28 | 119.9 |
C13—Ir1—C9 | 96.3 (2) | C23—C28—H28 | 119.9 |
C16—Ir1—C9 | 36.56 (13) | C22—C17—C18 | 119.5 (3) |
C1—Ir1—P1 | 89.72 (16) | C22—C17—P1 | 122.0 (2) |
C12—Ir1—P1 | 98.70 (9) | C18—C17—P1 | 118.5 (2) |
C13—Ir1—P1 | 90.55 (17) | C20—C21—C22 | 120.1 (3) |
C16—Ir1—P1 | 156.29 (9) | C20—C21—H21 | 120.0 |
C9—Ir1—P1 | 167.06 (11) | C22—C21—H21 | 120.0 |
N1—C1—N2 | 105.1 (5) | C9—C16—C15 | 124.7 (4) |
N1—C1—Ir1 | 131.3 (4) | C9—C16—Ir1 | 72.0 (2) |
N2—C1—Ir1 | 123.6 (3) | C15—C16—Ir1 | 113.0 (2) |
C12—C13—C14 | 124.8 (5) | C9—C16—H16 | 113.4 |
C12—C13—Ir1 | 71.2 (3) | C15—C16—H16 | 113.4 |
C14—C13—Ir1 | 110.7 (4) | Ir1—C16—H16 | 113.4 |
C12—C13—H13 | 114.1 | C31—C30—C29 | 120.5 (3) |
C14—C13—H13 | 114.1 | C31—C30—H30 | 119.8 |
Ir1—C13—H13 | 114.1 | C29—C30—H30 | 119.8 |
C13—C14—C15 | 112.4 (4) | C3—C2—N1 | 107.1 (3) |
C13—C14—H14A | 109.1 | C3—C2—H2 | 126.5 |
C15—C14—H14A | 109.1 | N1—C2—H2 | 126.5 |
C13—C14—H14B | 109.1 | C32—C33—C34 | 119.7 (4) |
C15—C14—H14B | 109.1 | C32—C33—H33 | 120.2 |
H14A—C14—H14B | 107.9 | C34—C33—H33 | 120.2 |
C1—N1—C2 | 110.4 (3) | C31—C32—C33 | 120.0 (3) |
C1—N1—C6 | 125.7 (4) | C31—C32—H32 | 120.0 |
C2—N1—C6 | 123.8 (3) | C33—C32—H32 | 120.0 |
C1—N2—C3 | 110.9 (3) | C25—C24—C23 | 121.3 (3) |
C1—N2—C4 | 124.0 (3) | C25—C24—H24 | 119.4 |
C3—N2—C4 | 124.9 (3) | C23—C24—H24 | 119.4 |
N2—C4—C5 | 112.5 (3) | C12—C11—C10 | 112.3 (3) |
N2—C4—H4A | 109.1 | C12—C11—H11A | 109.1 |
C5—C4—H4A | 109.1 | C10—C11—H11A | 109.1 |
N2—C4—H4B | 109.1 | C12—C11—H11B | 109.1 |
C5—C4—H4B | 109.1 | C10—C11—H11B | 109.1 |
H4A—C4—H4B | 107.8 | H11A—C11—H11B | 107.9 |
C2—C3—N2 | 106.5 (3) | C21—C20—C19 | 120.1 (3) |
C2—C3—H3 | 126.8 | C21—C20—H20 | 120.0 |
N2—C3—H3 | 126.8 | C19—C20—H20 | 120.0 |
C13—C12—C11 | 124.3 (4) | C27—C26—C25 | 119.7 (3) |
C13—C12—Ir1 | 71.5 (3) | C27—C26—H26 | 120.1 |
C11—C12—Ir1 | 112.6 (2) | C25—C26—H26 | 120.1 |
C13—C12—H12 | 113.7 | C4—C5—H5A | 109.5 |
C11—C12—H12 | 113.7 | C4—C5—H5B | 109.5 |
Ir1—C12—H12 | 113.7 | H5A—C5—H5B | 109.5 |
N1—C6—C7 | 111.0 (3) | C4—C5—H5C | 109.5 |
N1—C6—C8 | 110.1 (3) | H5A—C5—H5C | 109.5 |
C7—C6—C8 | 111.1 (3) | H5B—C5—H5C | 109.5 |
N1—C6—H6 | 108.2 | C26—C27—C28 | 120.6 (3) |
C7—C6—H6 | 108.2 | C26—C27—H27 | 119.7 |
C8—C6—H6 | 108.2 | C28—C27—H27 | 119.7 |
C17—P1—C23 | 102.75 (16) | C6—C8—H8A | 109.5 |
C17—P1—C29 | 104.30 (16) | C6—C8—H8B | 109.5 |
C23—P1—C29 | 105.38 (16) | H8A—C8—H8B | 109.5 |
C17—P1—Ir1 | 108.98 (11) | C6—C8—H8C | 109.5 |
C23—P1—Ir1 | 117.10 (12) | H8A—C8—H8C | 109.5 |
C29—P1—Ir1 | 116.74 (13) | H8B—C8—H8C | 109.5 |
C16—C9—C10 | 126.1 (5) | C32—C31—C30 | 120.6 (3) |
C16—C9—Ir1 | 71.5 (2) | C32—C31—H31 | 119.7 |
C10—C9—Ir1 | 107.6 (3) | C30—C31—H31 | 119.7 |
C16—C9—H9 | 114.3 | C16—C15—C14 | 113.0 (3) |
C10—C9—H9 | 114.3 | C16—C15—H15A | 109.0 |
Ir1—C9—H9 | 114.3 | C14—C15—H15A | 109.0 |
C9—C10—C11 | 113.2 (3) | C16—C15—H15B | 109.0 |
C9—C10—H10A | 108.9 | C14—C15—H15B | 109.0 |
C11—C10—H10A | 108.9 | H15A—C15—H15B | 107.8 |
C9—C10—H10B | 108.9 | C24—C25—C26 | 119.8 (4) |
C11—C10—H10B | 108.9 | C24—C25—H25 | 120.1 |
H10A—C10—H10B | 107.8 | C26—C25—H25 | 120.1 |
C30—C29—C34 | 118.0 (3) | C6—C7—H7A | 109.5 |
C30—C29—P1 | 123.1 (3) | C6—C7—H7B | 109.5 |
C34—C29—P1 | 118.8 (2) | H7A—C7—H7B | 109.5 |
C24—C23—C28 | 118.3 (3) | C6—C7—H7C | 109.5 |
C24—C23—P1 | 122.1 (3) | H7A—C7—H7C | 109.5 |
C28—C23—P1 | 119.4 (3) | H7B—C7—H7C | 109.5 |
C17—C22—C21 | 120.0 (3) | F2—B1—F1 | 108.8 (4) |
C17—C22—H22 | 120.0 | F2—B1—F4 | 107.6 (4) |
C21—C22—H22 | 120.0 | F1—B1—F4 | 113.2 (4) |
C33—C34—C29 | 121.3 (3) | F2—B1—F3 | 109.6 (3) |
C33—C34—H34 | 119.4 | F1—B1—F3 | 109.0 (4) |
C29—C34—H34 | 119.4 | F4—B1—F3 | 108.5 (4) |
| | | |
C12—C13—C14—C15 | −44.5 (7) | P1—C23—C28—C27 | −176.1 (3) |
Ir1—C13—C14—C15 | 36.4 (5) | C21—C22—C17—C18 | 0.3 (5) |
N2—C1—N1—C2 | −1.4 (5) | C21—C22—C17—P1 | −177.5 (3) |
Ir1—C1—N1—C2 | 177.5 (4) | C19—C18—C17—C22 | −0.9 (5) |
N2—C1—N1—C6 | 175.8 (3) | C19—C18—C17—P1 | 177.0 (3) |
Ir1—C1—N1—C6 | −5.4 (7) | C23—P1—C17—C22 | 85.0 (3) |
N1—C1—N2—C3 | 1.3 (5) | C29—P1—C17—C22 | −24.8 (3) |
Ir1—C1—N2—C3 | −177.6 (3) | Ir1—P1—C17—C22 | −150.1 (3) |
N1—C1—N2—C4 | 176.3 (3) | C23—P1—C17—C18 | −92.8 (3) |
Ir1—C1—N2—C4 | −2.7 (6) | C29—P1—C17—C18 | 157.4 (3) |
C1—N2—C4—C5 | 118.7 (4) | Ir1—P1—C17—C18 | 32.0 (3) |
C3—N2—C4—C5 | −67.0 (4) | C17—C22—C21—C20 | 0.4 (5) |
C1—N2—C3—C2 | −0.8 (4) | C10—C9—C16—C15 | −7.2 (7) |
C4—N2—C3—C2 | −175.7 (3) | Ir1—C9—C16—C15 | −105.9 (3) |
C14—C13—C12—C11 | −2.6 (8) | C10—C9—C16—Ir1 | 98.6 (4) |
Ir1—C13—C12—C11 | −105.2 (4) | C34—C29—C30—C31 | −1.2 (5) |
C14—C13—C12—Ir1 | 102.6 (6) | P1—C29—C30—C31 | 173.9 (3) |
C1—N1—C6—C7 | 125.0 (4) | N2—C3—C2—N1 | −0.1 (4) |
C2—N1—C6—C7 | −58.1 (4) | C1—N1—C2—C3 | 0.9 (4) |
C1—N1—C6—C8 | −111.6 (4) | C6—N1—C2—C3 | −176.3 (3) |
C2—N1—C6—C8 | 65.2 (4) | C29—C34—C33—C32 | −0.8 (5) |
C16—C9—C10—C11 | −38.8 (6) | C34—C33—C32—C31 | −0.5 (6) |
Ir1—C9—C10—C11 | 40.8 (4) | C28—C23—C24—C25 | 0.4 (5) |
C17—P1—C29—C30 | 131.1 (3) | P1—C23—C24—C25 | 175.8 (3) |
C23—P1—C29—C30 | 23.3 (3) | C13—C12—C11—C10 | 95.9 (5) |
Ir1—P1—C29—C30 | −108.6 (3) | Ir1—C12—C11—C10 | 13.5 (4) |
C17—P1—C29—C34 | −53.9 (3) | C9—C10—C11—C12 | −36.7 (5) |
C23—P1—C29—C34 | −161.7 (3) | C22—C21—C20—C19 | −0.6 (6) |
Ir1—P1—C29—C34 | 66.4 (3) | C18—C19—C20—C21 | 0.0 (6) |
C17—P1—C23—C24 | 4.7 (3) | C25—C26—C27—C28 | −1.2 (5) |
C29—P1—C23—C24 | 113.6 (3) | C23—C28—C27—C26 | 0.9 (5) |
Ir1—P1—C23—C24 | −114.7 (3) | C33—C32—C31—C30 | 0.9 (6) |
C17—P1—C23—C28 | −179.9 (3) | C29—C30—C31—C32 | −0.1 (6) |
C29—P1—C23—C28 | −71.0 (3) | C9—C16—C15—C14 | 95.5 (4) |
Ir1—P1—C23—C28 | 60.7 (3) | Ir1—C16—C15—C14 | 12.2 (4) |
C30—C29—C34—C33 | 1.6 (5) | C13—C14—C15—C16 | −32.1 (5) |
P1—C29—C34—C33 | −173.6 (3) | C23—C24—C25—C26 | −0.7 (6) |
C17—C18—C19—C20 | 0.8 (6) | C27—C26—C25—C24 | 1.1 (6) |
C24—C23—C28—C27 | −0.5 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···F1 | 0.99 | 2.43 | 3.153 (5) | 130 |
C28—H28···F3 | 0.95 | 2.58 | 3.265 (4) | 130 |
C28—H28···F1 | 0.95 | 2.52 | 3.474 (6) | 178 |
C11—H11B···F4 | 0.99 | 2.60 | 3.357 (5) | 134 |
C19—H19···F3i | 0.95 | 2.60 | 3.390 (5) | 141 |
C16—H16···F2i | 1.00 | 2.66 | 3.134 (4) | 109 |
C16—H16···F2i | 1.00 | 2.66 | 3.134 (4) | 109 |
C2—H2···F4ii | 0.95 | 2.56 | 3.116 (5) | 117 |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, y+1/2, z. |