Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113016636/yp3034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113016636/yp3034Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113016636/yp3034IIsup3.hkl |
CCDC references: 964743; 964744
The interest in the chemistry of alkynylgold(I) complexes is driven by their important photophysical and photochemical properties (Hong et al., 1994; Yam et al., 1996; Tzeng et al., 1996; Xiao et al., 1996). In addition, some show liquid-crystalline properties (Alejos et al., 1995; Irwin et al., 1996) or nonlinear optical behavior (Whitthall et al., 1997). Further, the linearity of the C≡C bond, coupled with the linear coordination preference of AuI, makes these complexes attractive candidates for the design of new compounds with extended backbone electronic conjugation (Vicente et al., 1997). The majority of the alkynylgold(I) complexes reported to date have the general formula R—C≡C—Au—L, where R is an organic group and L is usually a phosphane. Fascinating examples, such as macrocycles and catenanes (Puddephatt, 2008), have been reported using a combination of bridging organic groups and phosphane ligands.
Compounds of the general formula [Au(C≡C—R)2]- are less well studied (Vicente et al., 1997), although the use of the linear R—C≡C—Au—C≡C—R spacer between two donor groups has been recently accomplished by using pyridine-based fragments as the R group. In this context, there are only a few examples linking donor groups via the linear C≡C—Au—C≡C spacer (Ferrer et al., 2003, 2008; Manbeck et al., 2010; Emeljanenko et al., 2011; Vicente et al.; 2008), or using this spacer to connect other functional groups that contain hydrogen-bonding or π–π stacking associative synthons in one molecule. We have started a project to explore the possibility of using these linear spacers between various groups. To this end, we report here the preparation of two dialkynylgold(I) compounds, (I) and (II), functionalized with either the multidentate tris(pyrazolyl)methane scorpionate ligand or the strong π–π stacking 1,8-naphthalimide tecton.
All operations were carried out under a nitrogen atmosphere using standard Schlenk techniques and a Vacuum Atmospheres HE-493 dry box. All solvents were dried and distilled prior to use following standard techniques. The 1H NMR spectra were recorded on a Varian AM300 spectrometer. The alkynetris(pyrazolyl)methane (Reger et al., 2005) and (Pr4N)[Au(acac)2] (Vicente & Chicote, 1998) starting materials were prepared following literature methods. All other starting materials were obtained from commercial sources (Aldrich) and were used as received.
For the preparation of (I), a Schlenk flask was charged with a stirring bar, HC≡C—CH2—O—CH2—C(pz)3 (0.056 g, 0.2 mmol), (Pr4N)[Au(acac)2] (0.058 g, 0.1 mmol) and dichloromethane (25 ml). After 1 h of stirring at room temperature, the volatiles were removed under vacuum to afford a white powder (0.076 g, 80.5%), identified as (I). 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 7.69 (d, J = 1 Hz, 6H, H3-pz), 7.44 (d, J = 2 Hz, 6H, H5-pz), 6.37 (d of d, J = 2,1 Hz, 6H, H4-pz), 5.01 [s, 4H, OCH2C (pz)3], 4.42 (s, 4H, OCH2CC). Single crystals of (I) suitable for diffraction studies were grown over the course of a few days by layering a dichloromethane solution of the compound with hexanes.
Complex (II) was prepared as above, using HC≡C—CH2—NI (0.047 g, 0.2 mmol), affording a white powder (0.042 g, 49.2% based on NI) identified as (II). Slow evaporation of a deuterated chloroform solution of the compound afforded single crystals suitable for diffraction studies.
Crystal data, data collection and structure refinement details are summarized in Table 1. For both compounds, H atoms were introduced in idealized positions and treated as riding, with pyrazole C—H = 0.95 Å, methylene C—H = 0.99 Å and methyl C—H = 0.98 Å, and with Uiso(H) = 1.2Ueq(C) for pyrazole and methylene H, or Uiso(H) = 1.5Ueq(C) for methyl H.
The reaction of tetrapropylammonium bis(acetylacetonato)gold(I) with two equivalents of the alkyne-functionalized tris(pyrazolyl)methane ligand (see scheme) afforded tetrapropylammonium bis{3-[2,2,2-tris(1H-pyrazol-1-yl)ethoxy]prop-1-yn-1-yl}aurate(I), (I) (Fig. 1). The formation of the compound is indicated in its NMR spectrum by the disappearance of the C≡C—H signal (a triplet in the starting material) and the collapse of the methylene signal from a doublet to a singlet.
Bond lengths and angles in (I) fall within the normal range for this type of compound. The orientation of the three pyrazolyl rings is a propeller arrangement, with only one of the donor N atoms oriented toward the potential bonding `pocket' of the ligand. The two tris(pyrazolyl)methane units are positioned in a 'trans' orientation with respect to the C≡ C—Au—C≡C spacer. The C≡C—Au—C≡C group is not linear, presumably because of steric effects or crystal packing forces.
The (Pr4N)+ cations are positioned close to the [C≡C—Au—C≡C]- anions (Fig. 2). The anions are arranged within the crystal structure with the tris(pyrazolyl)methane groups from different building blocks oriented toward each other, without significant intermolecular interactions, forming a three-dimensional network containing channels accommodating the (Pr4N)+ counter-ions (Fig. 3).
The reaction of the same tetrapropylammonium bis(acetylacetonato)gold(I) with two equivalents of the alkyne-functionalized naphthalimide (NI) group (see scheme) afforded an unexpected gold(I) compound, tetrapropylammonium {η2-µ-3-[2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-3-yl]prop-1-yn-yl}bis{3-[2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-3-yl]prop-1-yn-1-yl}digold(I) deuterochloroform disolvate, (II) (Fig. 4), comprising a σ-bonded NI—CH2—C≡C—Au—C≡C—CH2—NI anionic unit [with (Pr4N)+ as counter-ion] that is π-coordinated to a neutral NI—CH2—C≡C—Au fragment. Bond lengths and angles fall within the normal range for this type of compound.
The crystal packing of (II) is based entirely on the π–π stacking interactions of the NI groups. The π-stacked NI units adopt two different orientations (Fig. 5). The NI fragments belonging to the σ-bonded part of the complex assume a `twisted' orientation in which the dipole vectors of the rings have a dihedral angle of approximately 120° (Fig. 5a), while the NI fragments belonging to the π-bonded part assume an antiparallel geometry in which the dipole vectors of the naphthalimides are oriented at 180° (Fig. 5b).
The first interaction generates chains, as pictured in Fig. 6, oriented along the ab diagonal of the unit cell. These chains are connected into two-dimensional sheets by the π–π stacking interaction of the second NI group, as pictured in Fig. 7. The distances between the Au atoms within these sheets (also shown in Fig. 7) are 25 Å between the σ-bonded Au atoms and 13 Å between the π-bonded Au atoms. These sheets are connected in a three-dimensional network, as pictured in Fig. 8, by multiple π–π stacking interactions involving the other sides of the NI units. The channels of this framework are filled with the (Pr4N)+ cations and two deuterated chloroform solvent molecules.
In conclusion, we have successfully shown that the C≡C—Au—C≡C spacer can be used in the design and synthesis of compounds containing multidentate donor groups or other functional groups that could be used in crystal engineering.
For related literature, see: Alejos et al. (1995); Emeljanenko et al. (2011); Ferrer et al. (2003, 2008); Hong et al. (1994); Irwin et al. (1996); Manbeck et al. (2010); Puddephatt (2008); Reger et al. (2005); Tzeng et al. (1996); Vicente & Chicote (1998); Vicente et al. (1997, 2008); Whitthall et al. (1997); Xiao et al. (1996); Yam et al. (1996).
The interest in the chemistry of alkynylgold(I) complexes is driven by their important photophysical and photochemical properties (Hong et al., 1994; Yam et al., 1996; Tzeng et al., 1996; Xiao et al., 1996). In addition, some show liquid-crystalline properties (Alejos et al., 1995; Irwin et al., 1996) or nonlinear optical behavior (Whitthall et al., 1997). Further, the linearity of the C≡C bond, coupled with the linear coordination preference of AuI, makes these complexes attractive candidates for the design of new compounds with extended backbone electronic conjugation (Vicente et al., 1997). The majority of the alkynylgold(I) complexes reported to date have the general formula R—C≡C—Au—L, where R is an organic group and L is usually a phosphane. Fascinating examples, such as macrocycles and catenanes (Puddephatt, 2008), have been reported using a combination of bridging organic groups and phosphane ligands.
Compounds of the general formula [Au(C≡C—R)2]- are less well studied (Vicente et al., 1997), although the use of the linear R—C≡C—Au—C≡C—R spacer between two donor groups has been recently accomplished by using pyridine-based fragments as the R group. In this context, there are only a few examples linking donor groups via the linear C≡C—Au—C≡C spacer (Ferrer et al., 2003, 2008; Manbeck et al., 2010; Emeljanenko et al., 2011; Vicente et al.; 2008), or using this spacer to connect other functional groups that contain hydrogen-bonding or π–π stacking associative synthons in one molecule. We have started a project to explore the possibility of using these linear spacers between various groups. To this end, we report here the preparation of two dialkynylgold(I) compounds, (I) and (II), functionalized with either the multidentate tris(pyrazolyl)methane scorpionate ligand or the strong π–π stacking 1,8-naphthalimide tecton.
The reaction of tetrapropylammonium bis(acetylacetonato)gold(I) with two equivalents of the alkyne-functionalized tris(pyrazolyl)methane ligand (see scheme) afforded tetrapropylammonium bis{3-[2,2,2-tris(1H-pyrazol-1-yl)ethoxy]prop-1-yn-1-yl}aurate(I), (I) (Fig. 1). The formation of the compound is indicated in its NMR spectrum by the disappearance of the C≡C—H signal (a triplet in the starting material) and the collapse of the methylene signal from a doublet to a singlet.
Bond lengths and angles in (I) fall within the normal range for this type of compound. The orientation of the three pyrazolyl rings is a propeller arrangement, with only one of the donor N atoms oriented toward the potential bonding `pocket' of the ligand. The two tris(pyrazolyl)methane units are positioned in a 'trans' orientation with respect to the C≡ C—Au—C≡C spacer. The C≡C—Au—C≡C group is not linear, presumably because of steric effects or crystal packing forces.
The (Pr4N)+ cations are positioned close to the [C≡C—Au—C≡C]- anions (Fig. 2). The anions are arranged within the crystal structure with the tris(pyrazolyl)methane groups from different building blocks oriented toward each other, without significant intermolecular interactions, forming a three-dimensional network containing channels accommodating the (Pr4N)+ counter-ions (Fig. 3).
The reaction of the same tetrapropylammonium bis(acetylacetonato)gold(I) with two equivalents of the alkyne-functionalized naphthalimide (NI) group (see scheme) afforded an unexpected gold(I) compound, tetrapropylammonium {η2-µ-3-[2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-3-yl]prop-1-yn-yl}bis{3-[2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-3-yl]prop-1-yn-1-yl}digold(I) deuterochloroform disolvate, (II) (Fig. 4), comprising a σ-bonded NI—CH2—C≡C—Au—C≡C—CH2—NI anionic unit [with (Pr4N)+ as counter-ion] that is π-coordinated to a neutral NI—CH2—C≡C—Au fragment. Bond lengths and angles fall within the normal range for this type of compound.
The crystal packing of (II) is based entirely on the π–π stacking interactions of the NI groups. The π-stacked NI units adopt two different orientations (Fig. 5). The NI fragments belonging to the σ-bonded part of the complex assume a `twisted' orientation in which the dipole vectors of the rings have a dihedral angle of approximately 120° (Fig. 5a), while the NI fragments belonging to the π-bonded part assume an antiparallel geometry in which the dipole vectors of the naphthalimides are oriented at 180° (Fig. 5b).
The first interaction generates chains, as pictured in Fig. 6, oriented along the ab diagonal of the unit cell. These chains are connected into two-dimensional sheets by the π–π stacking interaction of the second NI group, as pictured in Fig. 7. The distances between the Au atoms within these sheets (also shown in Fig. 7) are 25 Å between the σ-bonded Au atoms and 13 Å between the π-bonded Au atoms. These sheets are connected in a three-dimensional network, as pictured in Fig. 8, by multiple π–π stacking interactions involving the other sides of the NI units. The channels of this framework are filled with the (Pr4N)+ cations and two deuterated chloroform solvent molecules.
In conclusion, we have successfully shown that the C≡C—Au—C≡C spacer can be used in the design and synthesis of compounds containing multidentate donor groups or other functional groups that could be used in crystal engineering.
For related literature, see: Alejos et al. (1995); Emeljanenko et al. (2011); Ferrer et al. (2003, 2008); Hong et al. (1994); Irwin et al. (1996); Manbeck et al. (2010); Puddephatt (2008); Reger et al. (2005); Tzeng et al. (1996); Vicente & Chicote (1998); Vicente et al. (1997, 2008); Whitthall et al. (1997); Xiao et al. (1996); Yam et al. (1996).
All operations were carried out under a nitrogen atmosphere using standard Schlenk techniques and a Vacuum Atmospheres HE-493 dry box. All solvents were dried and distilled prior to use following standard techniques. The 1H NMR spectra were recorded on a Varian AM300 spectrometer. The alkynetris(pyrazolyl)methane (Reger et al., 2005) and (Pr4N)[Au(acac)2] (Vicente & Chicote, 1998) starting materials were prepared following literature methods. All other starting materials were obtained from commercial sources (Aldrich) and were used as received.
For the preparation of (I), a Schlenk flask was charged with a stirring bar, HC≡C—CH2—O—CH2—C(pz)3 (0.056 g, 0.2 mmol), (Pr4N)[Au(acac)2] (0.058 g, 0.1 mmol) and dichloromethane (25 ml). After 1 h of stirring at room temperature, the volatiles were removed under vacuum to afford a white powder (0.076 g, 80.5%), identified as (I). 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 7.69 (d, J = 1 Hz, 6H, H3-pz), 7.44 (d, J = 2 Hz, 6H, H5-pz), 6.37 (d of d, J = 2,1 Hz, 6H, H4-pz), 5.01 [s, 4H, OCH2C (pz)3], 4.42 (s, 4H, OCH2CC). Single crystals of (I) suitable for diffraction studies were grown over the course of a few days by layering a dichloromethane solution of the compound with hexanes.
Complex (II) was prepared as above, using HC≡C—CH2—NI (0.047 g, 0.2 mmol), affording a white powder (0.042 g, 49.2% based on NI) identified as (II). Slow evaporation of a deuterated chloroform solution of the compound afforded single crystals suitable for diffraction studies.
Crystal data, data collection and structure refinement details are summarized in Table 1. For both compounds, H atoms were introduced in idealized positions and treated as riding, with pyrazole C—H = 0.95 Å, methylene C—H = 0.99 Å and methyl C—H = 0.98 Å, and with Uiso(H) = 1.2Ueq(C) for pyrazole and methylene H, or Uiso(H) = 1.5Ueq(C) for methyl H.
For both compounds, data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme; some atom
labels have been omitted for clarity. Displacement ellipsoids are drawn at the
50% probability level. Fig. 2. The alternating arrangement of the cationic and anionic units in (I). Fig. 3. The three-dimensional network formed by the anionic [Au{C≡ CCH2OCH2C(pz)3}2]- fragments of (I), showing the channels containing the (Pr4N)+ counter-ions. Fig. 4. The [Au2(C15H8NO2)3]- anion of the naphthalimide gold(I) σ,π-complex, (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Fig. 5. The two orientations of the π-stacked naphthalimide units in (II) (see text for discussion). Fig. 6. The chains formed by the `twisted' π–π stacking of the naphthalimide groups in (II). Fig. 7. The two-dimensional sheets formed by the association of two symmetry-related chains, based on the antiparallel arrangement of the π–π stacking of the naphthalimide groups. Fig. 8. The three-dimensional network of (II), showing the channels which contain the (Pr4N)+ counter-ions and the two deuterated chloroform solvent molecules (not shown). |
(C16H28N)[Au(C14H13N6O)2] | F(000) = 1920 |
Mr = 945.93 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4064 (5) Å | Cell parameters from 9288 reflections |
b = 13.3301 (7) Å | θ = 2.2–26.5° |
c = 38.100 (2) Å | µ = 3.50 mm−1 |
β = 90.651 (1)° | T = 150 K |
V = 4269.2 (4) Å3 | Plate, colourless |
Z = 4 | 0.44 × 0.40 × 0.18 mm |
Bruker SMART APEX CCD area-detector diffractometer | 8791 independent reflections |
Radiation source: fine-focus sealed tube | 8217 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 26.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→10 |
Tmin = 0.308, Tmax = 0.572 | k = −16→16 |
37378 measured reflections | l = −47→47 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0199P)2 + 7.2785P] where P = (Fo2 + 2Fc2)/3 |
8791 reflections | (Δ/σ)max = 0.001 |
509 parameters | Δρmax = 0.91 e Å−3 |
0 restraints | Δρmin = −1.96 e Å−3 |
(C16H28N)[Au(C14H13N6O)2] | V = 4269.2 (4) Å3 |
Mr = 945.93 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.4064 (5) Å | µ = 3.50 mm−1 |
b = 13.3301 (7) Å | T = 150 K |
c = 38.100 (2) Å | 0.44 × 0.40 × 0.18 mm |
β = 90.651 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 8791 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 8217 reflections with I > 2σ(I) |
Tmin = 0.308, Tmax = 0.572 | Rint = 0.027 |
37378 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.19 | Δρmax = 0.91 e Å−3 |
8791 reflections | Δρmin = −1.96 e Å−3 |
509 parameters |
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 | ||
Au1 | 0.447078 (13) | 0.419306 (9) | 0.237321 (3) | 0.02415 (4) | |
C1 | 0.7504 (3) | 0.4255 (2) | 0.08082 (8) | 0.0215 (6) | |
C2 | 0.6891 (3) | 0.3546 (2) | 0.10910 (8) | 0.0251 (6) | |
H2A | 0.7462 | 0.2897 | 0.1082 | 0.030* | |
H2B | 0.7058 | 0.3843 | 0.1327 | 0.030* | |
C3 | 0.4563 (4) | 0.2721 (2) | 0.12674 (8) | 0.0275 (7) | |
H3A | 0.5163 | 0.2083 | 0.1264 | 0.033* | |
H3B | 0.3453 | 0.2576 | 0.1194 | 0.033* | |
C4 | 0.4571 (4) | 0.3126 (2) | 0.16263 (9) | 0.0275 (7) | |
C5 | 0.4638 (4) | 0.3508 (2) | 0.19135 (8) | 0.0269 (7) | |
C6 | 0.2252 (3) | 0.4578 (2) | 0.41144 (8) | 0.0217 (6) | |
C7 | 0.2529 (4) | 0.4608 (2) | 0.37161 (8) | 0.0283 (7) | |
H7A | 0.3680 | 0.4538 | 0.3669 | 0.034* | |
H7B | 0.1968 | 0.4039 | 0.3602 | 0.034* | |
C8 | 0.3141 (4) | 0.6029 (3) | 0.33643 (9) | 0.0319 (7) | |
H8A | 0.4084 | 0.6178 | 0.3513 | 0.038* | |
H8B | 0.2700 | 0.6675 | 0.3280 | 0.038* | |
C9 | 0.3639 (4) | 0.5432 (3) | 0.30614 (9) | 0.0284 (7) | |
C10 | 0.4061 (4) | 0.4937 (2) | 0.28144 (8) | 0.0264 (7) | |
C11 | 0.5649 (4) | 0.5576 (3) | 0.10564 (10) | 0.0321 (8) | |
H11 | 0.5021 | 0.5174 | 0.1207 | 0.039* | |
C12 | 0.5496 (4) | 0.6583 (3) | 0.09991 (10) | 0.0372 (8) | |
H12 | 0.4739 | 0.7025 | 0.1099 | 0.045* | |
C13 | 0.6685 (4) | 0.6820 (3) | 0.07642 (10) | 0.0390 (9) | |
H13 | 0.6869 | 0.7479 | 0.0678 | 0.047* | |
C21 | 1.0316 (4) | 0.4334 (2) | 0.05716 (9) | 0.0292 (7) | |
H21 | 1.0102 | 0.4301 | 0.0327 | 0.035* | |
C22 | 1.1777 (4) | 0.4432 (3) | 0.07306 (10) | 0.0356 (8) | |
H22 | 1.2783 | 0.4472 | 0.0620 | 0.043* | |
C23 | 1.1472 (4) | 0.4460 (3) | 0.10855 (11) | 0.0378 (8) | |
H23 | 1.2273 | 0.4524 | 0.1262 | 0.045* | |
C31 | 0.6559 (5) | 0.4366 (3) | 0.01729 (10) | 0.0476 (10) | |
H31 | 0.6451 | 0.5071 | 0.0145 | 0.057* | |
C32 | 0.6247 (6) | 0.3647 (4) | −0.00733 (11) | 0.0598 (13) | |
H32 | 0.5872 | 0.3748 | −0.0307 | 0.072* | |
C33 | 0.6587 (4) | 0.2744 (3) | 0.00874 (10) | 0.0382 (8) | |
H33 | 0.6459 | 0.2108 | −0.0022 | 0.046* | |
C41 | −0.0703 (4) | 0.4807 (2) | 0.40154 (8) | 0.0260 (6) | |
H41 | −0.0711 | 0.5042 | 0.3780 | 0.031* | |
C42 | −0.1979 (4) | 0.4761 (3) | 0.42362 (10) | 0.0321 (7) | |
H42 | −0.3050 | 0.4943 | 0.4186 | 0.039* | |
C43 | −0.1353 (4) | 0.4386 (3) | 0.45502 (9) | 0.0318 (7) | |
H43 | −0.1971 | 0.4270 | 0.4754 | 0.038* | |
C51 | 0.4077 (4) | 0.3695 (3) | 0.45518 (9) | 0.0334 (7) | |
H51 | 0.4261 | 0.4217 | 0.4717 | 0.040* | |
C52 | 0.4683 (4) | 0.2750 (3) | 0.45638 (10) | 0.0398 (9) | |
H52 | 0.5385 | 0.2479 | 0.4736 | 0.048* | |
C53 | 0.4061 (4) | 0.2265 (3) | 0.42706 (11) | 0.0381 (8) | |
H53 | 0.4278 | 0.1585 | 0.4213 | 0.046* | |
C61 | 0.1934 (4) | 0.6179 (2) | 0.44654 (9) | 0.0286 (7) | |
H61 | 0.0842 | 0.6134 | 0.4524 | 0.034* | |
C62 | 0.2950 (5) | 0.6937 (3) | 0.45502 (10) | 0.0381 (8) | |
H62 | 0.2718 | 0.7526 | 0.4680 | 0.046* | |
C63 | 0.4403 (5) | 0.6667 (3) | 0.44053 (11) | 0.0422 (9) | |
H63 | 0.5344 | 0.7057 | 0.4426 | 0.051* | |
N11 | 0.7534 (4) | 0.6033 (2) | 0.06725 (8) | 0.0347 (7) | |
N12 | 0.6875 (3) | 0.52639 (19) | 0.08553 (7) | 0.0245 (5) | |
N21 | 0.9933 (3) | 0.4387 (2) | 0.11523 (8) | 0.0365 (7) | |
N22 | 0.9240 (3) | 0.42953 (19) | 0.08314 (7) | 0.0241 (5) | |
N31 | 0.7110 (3) | 0.2870 (2) | 0.04102 (8) | 0.0310 (6) | |
N32 | 0.7051 (3) | 0.38739 (19) | 0.04632 (7) | 0.0227 (5) | |
N41 | 0.0193 (3) | 0.4209 (2) | 0.45347 (7) | 0.0272 (6) | |
N42 | 0.0573 (3) | 0.44506 (18) | 0.41988 (7) | 0.0208 (5) | |
N51 | 0.3130 (3) | 0.2859 (2) | 0.40806 (8) | 0.0322 (6) | |
N52 | 0.3158 (3) | 0.37429 (19) | 0.42580 (7) | 0.0244 (5) | |
N61 | 0.4317 (3) | 0.5800 (2) | 0.42347 (9) | 0.0365 (7) | |
N62 | 0.2782 (3) | 0.55023 (19) | 0.42807 (7) | 0.0249 (5) | |
O1 | 0.5253 (2) | 0.34036 (16) | 0.10230 (5) | 0.0244 (4) | |
O2 | 0.1963 (3) | 0.55245 (18) | 0.35732 (6) | 0.0328 (5) | |
N71 | −0.0066 (3) | 0.60395 (19) | 0.21635 (7) | 0.0229 (5) | |
C71 | −0.0170 (4) | 0.6042 (2) | 0.25654 (8) | 0.0271 (7) | |
H71A | 0.0576 | 0.5534 | 0.2661 | 0.033* | |
H71B | 0.0177 | 0.6706 | 0.2654 | 0.033* | |
C72 | −0.1833 (4) | 0.5823 (3) | 0.27032 (9) | 0.0363 (8) | |
H72A | −0.2580 | 0.6354 | 0.2625 | 0.044* | |
H72B | −0.2218 | 0.5173 | 0.2609 | 0.044* | |
C73 | −0.1771 (5) | 0.5786 (3) | 0.30996 (9) | 0.0429 (9) | |
H73A | −0.1026 | 0.5261 | 0.3176 | 0.064* | |
H73B | −0.2833 | 0.5636 | 0.3189 | 0.064* | |
H73C | −0.1414 | 0.6436 | 0.3191 | 0.064* | |
C74 | 0.1678 (4) | 0.6122 (2) | 0.20648 (9) | 0.0278 (7) | |
H74A | 0.2257 | 0.5548 | 0.2171 | 0.033* | |
H74B | 0.1756 | 0.6055 | 0.1807 | 0.033* | |
C75 | 0.2514 (4) | 0.7081 (3) | 0.21747 (10) | 0.0359 (8) | |
H75A | 0.2522 | 0.7140 | 0.2434 | 0.043* | |
H75B | 0.1943 | 0.7668 | 0.2076 | 0.043* | |
C76 | 0.4212 (4) | 0.7060 (3) | 0.20409 (12) | 0.0488 (10) | |
H76A | 0.4758 | 0.6464 | 0.2132 | 0.073* | |
H76B | 0.4775 | 0.7664 | 0.2120 | 0.073* | |
H76C | 0.4196 | 0.7039 | 0.1784 | 0.073* | |
C77 | −0.0725 (4) | 0.5068 (2) | 0.20094 (8) | 0.0261 (6) | |
H77A | −0.1890 | 0.5056 | 0.2045 | 0.031* | |
H77B | −0.0540 | 0.5070 | 0.1753 | 0.031* | |
C78 | −0.0018 (4) | 0.4111 (3) | 0.21632 (10) | 0.0370 (8) | |
H78A | 0.1145 | 0.4105 | 0.2126 | 0.044* | |
H78B | −0.0206 | 0.4093 | 0.2419 | 0.044* | |
C79 | −0.0754 (5) | 0.3199 (3) | 0.19937 (11) | 0.0403 (9) | |
H79A | −0.1907 | 0.3208 | 0.2029 | 0.060* | |
H79B | −0.0302 | 0.2592 | 0.2100 | 0.060* | |
H79C | −0.0532 | 0.3203 | 0.1742 | 0.060* | |
C80 | −0.1013 (4) | 0.6923 (2) | 0.20175 (9) | 0.0272 (7) | |
H80A | −0.2153 | 0.6805 | 0.2065 | 0.033* | |
H80B | −0.0692 | 0.7533 | 0.2149 | 0.033* | |
C81 | −0.0841 (4) | 0.7133 (3) | 0.16298 (9) | 0.0345 (8) | |
H81A | −0.1288 | 0.6570 | 0.1491 | 0.041* | |
H81B | 0.0299 | 0.7202 | 0.1572 | 0.041* | |
C82 | −0.1720 (5) | 0.8099 (3) | 0.15386 (10) | 0.0394 (8) | |
H82A | −0.2849 | 0.8023 | 0.1594 | 0.059* | |
H82B | −0.1609 | 0.8240 | 0.1288 | 0.059* | |
H82C | −0.1268 | 0.8654 | 0.1675 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.02221 (7) | 0.02898 (7) | 0.02129 (7) | 0.00289 (5) | 0.00172 (4) | −0.00015 (5) |
C1 | 0.0173 (14) | 0.0237 (15) | 0.0234 (15) | 0.0011 (11) | −0.0017 (11) | −0.0025 (12) |
C2 | 0.0200 (14) | 0.0297 (16) | 0.0256 (16) | 0.0004 (12) | −0.0026 (12) | 0.0022 (13) |
C3 | 0.0301 (16) | 0.0274 (16) | 0.0252 (16) | −0.0050 (13) | 0.0011 (13) | 0.0004 (13) |
C4 | 0.0250 (16) | 0.0266 (16) | 0.0309 (17) | −0.0025 (12) | 0.0028 (13) | 0.0029 (13) |
C5 | 0.0267 (16) | 0.0287 (16) | 0.0252 (16) | 0.0009 (13) | 0.0030 (12) | −0.0004 (13) |
C6 | 0.0173 (14) | 0.0204 (14) | 0.0275 (16) | 0.0001 (11) | 0.0028 (12) | 0.0013 (12) |
C7 | 0.0309 (17) | 0.0261 (16) | 0.0282 (17) | 0.0080 (13) | 0.0085 (13) | 0.0007 (13) |
C8 | 0.0374 (19) | 0.0289 (17) | 0.0296 (17) | 0.0058 (14) | 0.0103 (14) | 0.0048 (13) |
C9 | 0.0243 (16) | 0.0337 (17) | 0.0273 (17) | 0.0019 (13) | 0.0025 (13) | 0.0058 (14) |
C10 | 0.0246 (15) | 0.0343 (17) | 0.0204 (15) | 0.0027 (13) | 0.0029 (12) | −0.0010 (13) |
C11 | 0.0203 (15) | 0.0349 (18) | 0.0412 (19) | 0.0010 (13) | 0.0001 (14) | −0.0139 (15) |
C12 | 0.0300 (18) | 0.0338 (19) | 0.048 (2) | 0.0103 (15) | −0.0126 (16) | −0.0166 (16) |
C13 | 0.042 (2) | 0.0239 (17) | 0.051 (2) | −0.0001 (15) | −0.0110 (17) | −0.0017 (16) |
C21 | 0.0235 (15) | 0.0293 (17) | 0.0350 (18) | −0.0007 (13) | 0.0047 (13) | −0.0034 (14) |
C22 | 0.0197 (16) | 0.0345 (19) | 0.053 (2) | −0.0014 (13) | 0.0054 (15) | −0.0044 (16) |
C23 | 0.0213 (16) | 0.043 (2) | 0.049 (2) | −0.0003 (14) | −0.0092 (15) | −0.0066 (17) |
C31 | 0.063 (3) | 0.044 (2) | 0.035 (2) | 0.0136 (19) | −0.0163 (19) | 0.0008 (17) |
C32 | 0.077 (3) | 0.068 (3) | 0.033 (2) | 0.019 (3) | −0.025 (2) | −0.012 (2) |
C33 | 0.0303 (18) | 0.046 (2) | 0.039 (2) | 0.0020 (15) | −0.0026 (15) | −0.0192 (17) |
C41 | 0.0223 (15) | 0.0305 (16) | 0.0251 (16) | 0.0018 (12) | −0.0067 (12) | −0.0023 (13) |
C42 | 0.0181 (15) | 0.0353 (18) | 0.043 (2) | 0.0007 (13) | 0.0013 (14) | −0.0024 (15) |
C43 | 0.0279 (17) | 0.0333 (18) | 0.0344 (18) | −0.0041 (13) | 0.0083 (14) | 0.0007 (14) |
C51 | 0.0291 (17) | 0.041 (2) | 0.0302 (18) | 0.0009 (15) | −0.0021 (14) | 0.0049 (15) |
C52 | 0.0294 (18) | 0.043 (2) | 0.047 (2) | 0.0084 (15) | −0.0007 (16) | 0.0160 (17) |
C53 | 0.0310 (18) | 0.0274 (18) | 0.056 (2) | 0.0078 (14) | 0.0056 (16) | 0.0071 (16) |
C61 | 0.0295 (17) | 0.0248 (15) | 0.0315 (17) | −0.0010 (13) | 0.0001 (13) | −0.0016 (13) |
C62 | 0.048 (2) | 0.0277 (18) | 0.039 (2) | −0.0077 (15) | −0.0014 (16) | −0.0041 (15) |
C63 | 0.038 (2) | 0.036 (2) | 0.052 (2) | −0.0160 (16) | −0.0058 (17) | 0.0017 (17) |
N11 | 0.0341 (16) | 0.0255 (15) | 0.0445 (18) | −0.0023 (12) | −0.0008 (13) | 0.0014 (12) |
N12 | 0.0208 (12) | 0.0219 (13) | 0.0307 (14) | 0.0009 (10) | −0.0014 (10) | −0.0043 (11) |
N21 | 0.0233 (14) | 0.056 (2) | 0.0301 (15) | −0.0013 (13) | −0.0080 (12) | −0.0055 (14) |
N22 | 0.0168 (12) | 0.0300 (14) | 0.0256 (13) | 0.0013 (10) | −0.0021 (10) | −0.0032 (11) |
N31 | 0.0320 (15) | 0.0272 (14) | 0.0338 (15) | 0.0026 (11) | −0.0003 (12) | −0.0077 (12) |
N32 | 0.0205 (12) | 0.0241 (13) | 0.0236 (13) | 0.0017 (10) | −0.0026 (10) | −0.0020 (10) |
N41 | 0.0256 (13) | 0.0300 (14) | 0.0259 (13) | −0.0038 (11) | 0.0032 (11) | 0.0056 (11) |
N42 | 0.0162 (12) | 0.0235 (12) | 0.0228 (13) | −0.0005 (9) | −0.0002 (10) | −0.0016 (10) |
N51 | 0.0291 (14) | 0.0209 (13) | 0.0467 (18) | 0.0016 (11) | −0.0010 (13) | 0.0005 (12) |
N52 | 0.0200 (12) | 0.0222 (13) | 0.0310 (14) | 0.0024 (10) | 0.0012 (10) | 0.0021 (11) |
N61 | 0.0204 (13) | 0.0367 (16) | 0.0522 (19) | −0.0063 (12) | 0.0009 (13) | 0.0024 (14) |
N62 | 0.0171 (12) | 0.0236 (13) | 0.0340 (15) | −0.0030 (10) | 0.0000 (11) | −0.0004 (11) |
O1 | 0.0207 (10) | 0.0318 (12) | 0.0208 (10) | −0.0053 (9) | −0.0020 (8) | 0.0036 (9) |
O2 | 0.0340 (13) | 0.0331 (12) | 0.0314 (12) | 0.0116 (10) | 0.0125 (10) | 0.0090 (10) |
N71 | 0.0188 (12) | 0.0255 (13) | 0.0242 (13) | 0.0011 (10) | −0.0032 (10) | −0.0008 (10) |
C71 | 0.0356 (18) | 0.0239 (16) | 0.0219 (15) | −0.0026 (13) | 0.0033 (13) | 0.0001 (12) |
C72 | 0.0291 (17) | 0.051 (2) | 0.0284 (17) | −0.0045 (16) | 0.0002 (14) | −0.0043 (16) |
C73 | 0.041 (2) | 0.059 (2) | 0.0290 (18) | −0.0102 (18) | 0.0010 (15) | 0.0050 (18) |
C74 | 0.0193 (15) | 0.0313 (17) | 0.0327 (17) | 0.0023 (12) | −0.0007 (13) | 0.0014 (13) |
C75 | 0.0268 (17) | 0.0390 (19) | 0.042 (2) | −0.0049 (14) | 0.0049 (15) | −0.0064 (16) |
C76 | 0.0295 (19) | 0.051 (2) | 0.067 (3) | −0.0088 (17) | 0.0082 (18) | −0.004 (2) |
C77 | 0.0239 (15) | 0.0275 (16) | 0.0267 (16) | −0.0016 (12) | −0.0046 (12) | −0.0031 (13) |
C78 | 0.0382 (19) | 0.0284 (18) | 0.044 (2) | 0.0018 (15) | −0.0141 (16) | 0.0013 (15) |
C79 | 0.042 (2) | 0.0282 (18) | 0.050 (2) | −0.0004 (15) | −0.0081 (17) | 0.0013 (16) |
C80 | 0.0229 (15) | 0.0272 (16) | 0.0314 (17) | 0.0058 (12) | −0.0040 (13) | 0.0001 (13) |
C81 | 0.0379 (19) | 0.0337 (18) | 0.0318 (18) | 0.0028 (15) | −0.0043 (15) | 0.0053 (14) |
C82 | 0.044 (2) | 0.0337 (19) | 0.040 (2) | 0.0028 (16) | −0.0104 (17) | 0.0095 (16) |
Au1—C5 | 1.982 (3) | C52—H52 | 0.9500 |
Au1—C10 | 1.985 (3) | C52—C53 | 1.388 (6) |
C1—C2 | 1.527 (4) | C53—H53 | 0.9500 |
C1—N12 | 1.456 (4) | C53—N51 | 1.324 (4) |
C1—N22 | 1.462 (4) | C61—H61 | 0.9500 |
C1—N32 | 1.456 (4) | C61—C62 | 1.359 (5) |
C2—H2A | 0.9900 | C61—N62 | 1.352 (4) |
C2—H2B | 0.9900 | C62—H62 | 0.9500 |
C2—O1 | 1.412 (3) | C62—C63 | 1.393 (6) |
C3—H3A | 0.9900 | C63—H63 | 0.9500 |
C3—H3B | 0.9900 | C63—N61 | 1.328 (5) |
C3—C4 | 1.470 (4) | N11—N12 | 1.361 (4) |
C3—O1 | 1.429 (4) | N21—N22 | 1.354 (4) |
C4—C5 | 1.208 (5) | N31—N32 | 1.355 (4) |
C6—C7 | 1.538 (4) | N41—N42 | 1.361 (4) |
C6—N42 | 1.461 (4) | N51—N52 | 1.358 (4) |
C6—N52 | 1.452 (4) | N61—N62 | 1.363 (4) |
C6—N62 | 1.453 (4) | N71—C71 | 1.535 (4) |
C7—H7A | 0.9900 | N71—C74 | 1.522 (4) |
C7—H7B | 0.9900 | N71—C77 | 1.524 (4) |
C7—O2 | 1.418 (4) | N71—C80 | 1.523 (4) |
C8—H8A | 0.9900 | C71—H71A | 0.9900 |
C8—H8B | 0.9900 | C71—H71B | 0.9900 |
C8—C9 | 1.466 (5) | C71—C72 | 1.527 (5) |
C8—O2 | 1.444 (4) | C72—H72A | 0.9900 |
C9—C10 | 1.206 (5) | C72—H72B | 0.9900 |
C11—H11 | 0.9500 | C72—C73 | 1.512 (5) |
C11—C12 | 1.366 (5) | C73—H73A | 0.9800 |
C11—N12 | 1.357 (4) | C73—H73B | 0.9800 |
C12—H12 | 0.9500 | C73—H73C | 0.9800 |
C12—C13 | 1.386 (6) | C74—H74A | 0.9900 |
C13—H13 | 0.9500 | C74—H74B | 0.9900 |
C13—N11 | 1.318 (5) | C74—C75 | 1.516 (5) |
C21—H21 | 0.9500 | C75—H75A | 0.9900 |
C21—C22 | 1.370 (5) | C75—H75B | 0.9900 |
C21—N22 | 1.349 (4) | C75—C76 | 1.521 (5) |
C22—H22 | 0.9500 | C76—H76A | 0.9800 |
C22—C23 | 1.380 (5) | C76—H76B | 0.9800 |
C23—H23 | 0.9500 | C76—H76C | 0.9800 |
C23—N21 | 1.324 (4) | C77—H77A | 0.9900 |
C31—H31 | 0.9500 | C77—H77B | 0.9900 |
C31—C32 | 1.365 (6) | C77—C78 | 1.522 (4) |
C31—N32 | 1.347 (5) | C78—H78A | 0.9900 |
C32—H32 | 0.9500 | C78—H78B | 0.9900 |
C32—C33 | 1.380 (6) | C78—C79 | 1.506 (5) |
C33—H33 | 0.9500 | C79—H79A | 0.9800 |
C33—N31 | 1.312 (4) | C79—H79B | 0.9800 |
C41—H41 | 0.9500 | C79—H79C | 0.9800 |
C41—C42 | 1.372 (5) | C80—H80A | 0.9900 |
C41—N42 | 1.359 (4) | C80—H80B | 0.9900 |
C42—H42 | 0.9500 | C80—C81 | 1.512 (5) |
C42—C43 | 1.394 (5) | C81—H81A | 0.9900 |
C43—H43 | 0.9500 | C81—H81B | 0.9900 |
C43—N41 | 1.323 (4) | C81—C82 | 1.522 (5) |
C51—H51 | 0.9500 | C82—H82A | 0.9800 |
C51—C52 | 1.359 (5) | C82—H82B | 0.9800 |
C51—N52 | 1.354 (4) | C82—H82C | 0.9800 |
C5—Au1—C10 | 173.38 (13) | C21—N22—C1 | 129.3 (3) |
N12—C1—C2 | 111.0 (2) | C21—N22—N21 | 111.9 (3) |
N12—C1—N22 | 108.8 (2) | N21—N22—C1 | 118.5 (2) |
N22—C1—C2 | 108.9 (2) | C33—N31—N32 | 104.7 (3) |
N32—C1—C2 | 109.5 (2) | C31—N32—C1 | 130.2 (3) |
N32—C1—N12 | 110.0 (2) | C31—N32—N31 | 111.7 (3) |
N32—C1—N22 | 108.5 (2) | N31—N32—C1 | 118.0 (2) |
C1—C2—H2A | 110.3 | C43—N41—N42 | 103.9 (3) |
C1—C2—H2B | 110.3 | C41—N42—C6 | 127.2 (3) |
H2A—C2—H2B | 108.6 | C41—N42—N41 | 111.9 (2) |
O1—C2—C1 | 106.9 (2) | N41—N42—C6 | 118.1 (2) |
O1—C2—H2A | 110.3 | C53—N51—N52 | 103.9 (3) |
O1—C2—H2B | 110.3 | C51—N52—C6 | 129.7 (3) |
H3A—C3—H3B | 107.9 | C51—N52—N51 | 112.1 (3) |
C4—C3—H3A | 109.2 | N51—N52—C6 | 118.1 (3) |
C4—C3—H3B | 109.2 | C63—N61—N62 | 103.7 (3) |
O1—C3—H3A | 109.2 | C61—N62—C6 | 129.2 (3) |
O1—C3—H3B | 109.2 | C61—N62—N61 | 112.2 (3) |
O1—C3—C4 | 112.0 (3) | N61—N62—C6 | 118.5 (3) |
C5—C4—C3 | 175.8 (3) | C2—O1—C3 | 111.6 (2) |
C4—C5—Au1 | 172.8 (3) | C7—O2—C8 | 112.6 (2) |
N42—C6—C7 | 112.2 (3) | C74—N71—C71 | 108.2 (2) |
N52—C6—C7 | 107.9 (2) | C74—N71—C77 | 108.2 (2) |
N52—C6—N42 | 109.4 (2) | C74—N71—C80 | 110.8 (2) |
N52—C6—N62 | 109.2 (2) | C77—N71—C71 | 111.2 (2) |
N62—C6—C7 | 111.0 (3) | C80—N71—C71 | 109.1 (2) |
N62—C6—N42 | 107.2 (2) | C80—N71—C77 | 109.3 (2) |
C6—C7—H7A | 109.6 | N71—C71—H71A | 108.8 |
C6—C7—H7B | 109.6 | N71—C71—H71B | 108.8 |
H7A—C7—H7B | 108.1 | H71A—C71—H71B | 107.7 |
O2—C7—C6 | 110.3 (2) | C72—C71—N71 | 113.9 (3) |
O2—C7—H7A | 109.6 | C72—C71—H71A | 108.8 |
O2—C7—H7B | 109.6 | C72—C71—H71B | 108.8 |
H8A—C8—H8B | 107.8 | C71—C72—H72A | 109.8 |
C9—C8—H8A | 109.1 | C71—C72—H72B | 109.8 |
C9—C8—H8B | 109.1 | H72A—C72—H72B | 108.3 |
O2—C8—H8A | 109.1 | C73—C72—C71 | 109.2 (3) |
O2—C8—H8B | 109.1 | C73—C72—H72A | 109.8 |
O2—C8—C9 | 112.6 (3) | C73—C72—H72B | 109.8 |
C10—C9—C8 | 179.3 (4) | C72—C73—H73A | 109.5 |
C9—C10—Au1 | 171.7 (3) | C72—C73—H73B | 109.5 |
C12—C11—H11 | 126.8 | C72—C73—H73C | 109.5 |
N12—C11—H11 | 126.8 | H73A—C73—H73B | 109.5 |
N12—C11—C12 | 106.4 (3) | H73A—C73—H73C | 109.5 |
C11—C12—H12 | 127.4 | H73B—C73—H73C | 109.5 |
C11—C12—C13 | 105.1 (3) | N71—C74—H74A | 108.3 |
C13—C12—H12 | 127.4 | N71—C74—H74B | 108.3 |
C12—C13—H13 | 123.7 | H74A—C74—H74B | 107.4 |
N11—C13—C12 | 112.7 (3) | C75—C74—N71 | 115.9 (3) |
N11—C13—H13 | 123.7 | C75—C74—H74A | 108.3 |
C22—C21—H21 | 126.7 | C75—C74—H74B | 108.3 |
N22—C21—H21 | 126.7 | C74—C75—H75A | 109.9 |
N22—C21—C22 | 106.5 (3) | C74—C75—H75B | 109.9 |
C21—C22—H22 | 127.5 | C74—C75—C76 | 109.0 (3) |
C21—C22—C23 | 105.1 (3) | H75A—C75—H75B | 108.3 |
C23—C22—H22 | 127.5 | C76—C75—H75A | 109.9 |
C22—C23—H23 | 123.9 | C76—C75—H75B | 109.9 |
N21—C23—C22 | 112.3 (3) | C75—C76—H76A | 109.5 |
N21—C23—H23 | 123.9 | C75—C76—H76B | 109.5 |
C32—C31—H31 | 127.0 | C75—C76—H76C | 109.5 |
N32—C31—H31 | 127.0 | H76A—C76—H76B | 109.5 |
N32—C31—C32 | 106.1 (4) | H76A—C76—H76C | 109.5 |
C31—C32—H32 | 127.1 | H76B—C76—H76C | 109.5 |
C31—C32—C33 | 105.7 (4) | N71—C77—H77A | 108.5 |
C33—C32—H32 | 127.1 | N71—C77—H77B | 108.5 |
C32—C33—H33 | 124.1 | H77A—C77—H77B | 107.5 |
N31—C33—C32 | 111.7 (3) | C78—C77—N71 | 115.2 (2) |
N31—C33—H33 | 124.1 | C78—C77—H77A | 108.5 |
C42—C41—H41 | 126.7 | C78—C77—H77B | 108.5 |
N42—C41—H41 | 126.7 | C77—C78—H78A | 109.5 |
N42—C41—C42 | 106.7 (3) | C77—C78—H78B | 109.5 |
C41—C42—H42 | 127.7 | H78A—C78—H78B | 108.1 |
C41—C42—C43 | 104.6 (3) | C79—C78—C77 | 110.8 (3) |
C43—C42—H42 | 127.7 | C79—C78—H78A | 109.5 |
C42—C43—H43 | 123.6 | C79—C78—H78B | 109.5 |
N41—C43—C42 | 112.8 (3) | C78—C79—H79A | 109.5 |
N41—C43—H43 | 123.6 | C78—C79—H79B | 109.5 |
C52—C51—H51 | 126.8 | C78—C79—H79C | 109.5 |
N52—C51—H51 | 126.8 | H79A—C79—H79B | 109.5 |
N52—C51—C52 | 106.4 (3) | H79A—C79—H79C | 109.5 |
C51—C52—H52 | 127.3 | H79B—C79—H79C | 109.5 |
C51—C52—C53 | 105.5 (3) | N71—C80—H80A | 108.2 |
C53—C52—H52 | 127.3 | N71—C80—H80B | 108.2 |
C52—C53—H53 | 124.0 | H80A—C80—H80B | 107.3 |
N51—C53—C52 | 112.1 (3) | C81—C80—N71 | 116.4 (3) |
N51—C53—H53 | 124.0 | C81—C80—H80A | 108.2 |
C62—C61—H61 | 126.7 | C81—C80—H80B | 108.2 |
N62—C61—H61 | 126.7 | C80—C81—H81A | 109.9 |
N62—C61—C62 | 106.6 (3) | C80—C81—H81B | 109.9 |
C61—C62—H62 | 127.3 | C80—C81—C82 | 109.1 (3) |
C61—C62—C63 | 105.3 (3) | H81A—C81—H81B | 108.3 |
C63—C62—H62 | 127.3 | C82—C81—H81A | 109.9 |
C62—C63—H63 | 123.9 | C82—C81—H81B | 109.9 |
N61—C63—C62 | 112.1 (3) | C81—C82—H82A | 109.5 |
N61—C63—H63 | 123.9 | C81—C82—H82B | 109.5 |
C13—N11—N12 | 103.9 (3) | C81—C82—H82C | 109.5 |
C11—N12—C1 | 129.2 (3) | H82A—C82—H82B | 109.5 |
C11—N12—N11 | 112.0 (3) | H82A—C82—H82C | 109.5 |
N11—N12—C1 | 118.8 (3) | H82B—C82—H82C | 109.5 |
C23—N21—N22 | 104.2 (3) | ||
C1—C2—O1—C3 | 178.1 (2) | N12—C1—C2—O1 | 69.6 (3) |
C2—C1—N12—C11 | −14.8 (4) | N12—C1—N22—C21 | −97.7 (4) |
C2—C1—N12—N11 | 167.0 (3) | N12—C1—N22—N21 | 76.4 (3) |
C2—C1—N22—C21 | 141.2 (3) | N12—C1—N32—C31 | 19.0 (5) |
C2—C1—N22—N21 | −44.7 (4) | N12—C1—N32—N31 | −160.9 (3) |
C2—C1—N32—C31 | 141.4 (4) | N12—C11—C12—C13 | −0.7 (4) |
C2—C1—N32—N31 | −38.6 (3) | N22—C1—C2—O1 | −170.7 (2) |
C4—C3—O1—C2 | 65.8 (3) | N22—C1—N12—C11 | −134.6 (3) |
C6—C7—O2—C8 | 128.2 (3) | N22—C1—N12—N11 | 47.2 (4) |
C7—C6—N42—C41 | −33.2 (4) | N22—C1—N32—C31 | −99.9 (4) |
C7—C6—N42—N41 | 166.9 (3) | N22—C1—N32—N31 | 80.2 (3) |
C7—C6—N52—C51 | 136.3 (3) | N22—C21—C22—C23 | −0.8 (4) |
C7—C6—N52—N51 | −43.3 (3) | N32—C1—C2—O1 | −52.1 (3) |
C7—C6—N62—C61 | 119.5 (3) | N32—C1—N12—C11 | 106.6 (4) |
C7—C6—N62—N61 | −55.9 (4) | N32—C1—N12—N11 | −71.5 (3) |
C9—C8—O2—C7 | 61.2 (4) | N32—C1—N22—C21 | 22.0 (4) |
C11—C12—C13—N11 | 0.6 (4) | N32—C1—N22—N21 | −163.9 (3) |
C12—C11—N12—C1 | −177.6 (3) | N32—C31—C32—C33 | −0.3 (5) |
C12—C11—N12—N11 | 0.6 (4) | N42—C6—C7—O2 | 72.1 (3) |
C12—C13—N11—N12 | −0.2 (4) | N42—C6—N52—C51 | −101.4 (4) |
C13—N11—N12—C1 | 178.2 (3) | N42—C6—N52—N51 | 79.0 (3) |
C13—N11—N12—C11 | −0.3 (4) | N42—C6—N62—C61 | −3.4 (4) |
C21—C22—C23—N21 | 0.0 (4) | N42—C6—N62—N61 | −178.7 (3) |
C22—C21—N22—C1 | 175.9 (3) | N42—C41—C42—C43 | 1.2 (4) |
C22—C21—N22—N21 | 1.5 (4) | N52—C6—C7—O2 | −167.4 (3) |
C22—C23—N21—N22 | 0.9 (4) | N52—C6—N42—C41 | −152.8 (3) |
C23—N21—N22—C1 | −176.5 (3) | N52—C6—N42—N41 | 47.3 (3) |
C23—N21—N22—C21 | −1.4 (4) | N52—C6—N62—C61 | −121.7 (3) |
C31—C32—C33—N31 | −1.2 (5) | N52—C6—N62—N61 | 62.9 (3) |
C32—C31—N32—C1 | −178.2 (3) | N52—C51—C52—C53 | −0.8 (4) |
C32—C31—N32—N31 | 1.7 (5) | N62—C6—C7—O2 | −47.8 (3) |
C32—C33—N31—N32 | 2.2 (4) | N62—C6—N42—C41 | 88.9 (3) |
C33—N31—N32—C1 | 177.5 (3) | N62—C6—N42—N41 | −71.0 (3) |
C33—N31—N32—C31 | −2.4 (4) | N62—C6—N52—C51 | 15.5 (4) |
C41—C42—C43—N41 | 0.3 (4) | N62—C6—N52—N51 | −164.0 (3) |
C42—C41—N42—C6 | −163.2 (3) | N62—C61—C62—C63 | 0.3 (4) |
C42—C41—N42—N41 | −2.3 (4) | N71—C71—C72—C73 | 176.7 (3) |
C42—C43—N41—N42 | −1.6 (4) | N71—C74—C75—C76 | −177.3 (3) |
C43—N41—N42—C6 | 165.2 (3) | N71—C77—C78—C79 | 179.8 (3) |
C43—N41—N42—C41 | 2.4 (3) | N71—C80—C81—C82 | −174.0 (3) |
C51—C52—C53—N51 | 0.6 (4) | C71—N71—C74—C75 | −63.4 (3) |
C52—C51—N52—C6 | −178.9 (3) | C71—N71—C77—C78 | −52.8 (4) |
C52—C51—N52—N51 | 0.7 (4) | C71—N71—C80—C81 | 171.0 (3) |
C52—C53—N51—N52 | −0.2 (4) | C74—N71—C71—C72 | −172.2 (3) |
C53—N51—N52—C6 | 179.3 (3) | C74—N71—C77—C78 | 65.9 (3) |
C53—N51—N52—C51 | −0.3 (4) | C74—N71—C80—C81 | 52.0 (4) |
C61—C62—C63—N61 | 0.9 (5) | C77—N71—C71—C72 | −53.5 (3) |
C62—C61—N62—C6 | −176.9 (3) | C77—N71—C74—C75 | 176.0 (3) |
C62—C61—N62—N61 | −1.3 (4) | C77—N71—C80—C81 | −67.2 (3) |
C62—C63—N61—N62 | −1.6 (4) | C80—N71—C71—C72 | 67.2 (3) |
C63—N61—N62—C6 | 177.9 (3) | C80—N71—C74—C75 | 56.2 (4) |
C63—N61—N62—C61 | 1.8 (4) | C80—N71—C77—C78 | −173.3 (3) |
(C12H28N)[Au2(C15H8NO2)3]·2CDCl3 | Z = 2 |
Mr = 1523.71 | F(000) = 1488 |
Triclinic, P1 | Dx = 1.795 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3493 (5) Å | Cell parameters from 3344 reflections |
b = 13.1970 (7) Å | θ = 2.4–20.4° |
c = 25.8732 (14) Å | µ = 5.54 mm−1 |
α = 85.084 (1)° | T = 150 K |
β = 89.936 (1)° | Needle, colourless |
γ = 82.957 (1)° | 0.20 × 0.04 × 0.02 mm |
V = 2818.8 (3) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 7339 independent reflections |
Radiation source: fine-focus sealed tube | 5638 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 22.5°, θmin = 0.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→8 |
Tmin = 0.750, Tmax = 1.000 | k = −14→14 |
20651 measured reflections | l = −27→27 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0571P)2 + 5.2206P] where P = (Fo2 + 2Fc2)/3 |
7339 reflections | (Δ/σ)max = 0.001 |
698 parameters | Δρmax = 2.21 e Å−3 |
0 restraints | Δρmin = −1.07 e Å−3 |
(C12H28N)[Au2(C15H8NO2)3]·2CDCl3 | γ = 82.957 (1)° |
Mr = 1523.71 | V = 2818.8 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3493 (5) Å | Mo Kα radiation |
b = 13.1970 (7) Å | µ = 5.54 mm−1 |
c = 25.8732 (14) Å | T = 150 K |
α = 85.084 (1)° | 0.20 × 0.04 × 0.02 mm |
β = 89.936 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 7339 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 5638 reflections with I > 2σ(I) |
Tmin = 0.750, Tmax = 1.000 | Rint = 0.064 |
20651 measured reflections | θmax = 22.5° |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | Δρmax = 2.21 e Å−3 |
7339 reflections | Δρmin = −1.07 e Å−3 |
698 parameters |
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. Compound crystallized from CDCl3. Deuterium atoms of CDCl3 solvent added to .INS file for correct FW and d(calc), as recommended (SHELXL97 manual). Weakly scattering tiny crystal, no diffraction above 2theta ca 45 degrees. 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 | ||
Au1 | 0.44506 (5) | 0.17401 (3) | 0.229084 (16) | 0.03058 (16) | |
Au2 | 0.39533 (6) | 0.27653 (3) | 0.347183 (17) | 0.03517 (16) | |
C1 | 0.5252 (14) | 0.1650 (10) | 0.3118 (4) | 0.037 (3) | |
C2 | 0.6028 (13) | 0.0964 (9) | 0.2922 (4) | 0.031 (3) | |
C3 | 0.7190 (14) | 0.0047 (9) | 0.2847 (4) | 0.042 (3) | |
H3A | 0.7021 | −0.0180 | 0.2498 | 0.050* | |
H3B | 0.8303 | 0.0228 | 0.2864 | 0.050* | |
C4 | 0.3395 (13) | 0.2105 (8) | 0.1602 (5) | 0.030 (3) | |
C5 | 0.2737 (13) | 0.2285 (8) | 0.1190 (5) | 0.031 (3) | |
C6 | 0.1905 (14) | 0.2442 (8) | 0.0691 (4) | 0.036 (3) | |
H6A | 0.0742 | 0.2393 | 0.0746 | 0.043* | |
H6B | 0.2330 | 0.1888 | 0.0474 | 0.043* | |
C7 | 0.2570 (15) | 0.3879 (9) | 0.3805 (4) | 0.037 (3) | |
C8 | 0.1580 (16) | 0.4525 (10) | 0.3953 (5) | 0.043 (3) | |
C9 | 0.0323 (14) | 0.5332 (8) | 0.4125 (5) | 0.039 (3) | |
H9A | −0.0632 | 0.5401 | 0.3892 | 0.046* | |
H9B | −0.0024 | 0.5129 | 0.4481 | 0.046* | |
C11 | 0.6158 (14) | −0.1591 (9) | 0.3090 (4) | 0.034 (3) | |
C12 | 0.6017 (13) | −0.2426 (9) | 0.3477 (5) | 0.036 (3) | |
C13 | 0.6677 (14) | −0.2429 (9) | 0.3976 (4) | 0.036 (3) | |
C14 | 0.7446 (13) | −0.1608 (9) | 0.4113 (4) | 0.035 (3) | |
C15 | 0.7598 (14) | −0.0722 (9) | 0.3727 (4) | 0.035 (3) | |
C16 | 0.5264 (15) | −0.3234 (10) | 0.3345 (5) | 0.050 (4) | |
H16 | 0.4839 | −0.3230 | 0.3004 | 0.060* | |
C17 | 0.5116 (16) | −0.4062 (11) | 0.3707 (6) | 0.054 (4) | |
H17 | 0.4581 | −0.4615 | 0.3612 | 0.065* | |
C18 | 0.5735 (16) | −0.4086 (10) | 0.4199 (6) | 0.054 (4) | |
H18 | 0.5630 | −0.4655 | 0.4442 | 0.065* | |
C19 | 0.6524 (16) | −0.3274 (9) | 0.4345 (5) | 0.046 (3) | |
C20 | 0.7201 (17) | −0.3247 (11) | 0.4844 (5) | 0.057 (4) | |
H20 | 0.7134 | −0.3808 | 0.5096 | 0.068* | |
C21 | 0.7939 (17) | −0.2447 (10) | 0.4974 (5) | 0.052 (4) | |
H21 | 0.8367 | −0.2448 | 0.5314 | 0.062* | |
C22 | 0.8079 (16) | −0.1601 (10) | 0.4601 (5) | 0.052 (4) | |
H22 | 0.8605 | −0.1040 | 0.4690 | 0.062* | |
C23 | 0.3065 (13) | 0.3433 (8) | −0.0031 (4) | 0.028 (3) | |
C24 | 0.3293 (13) | 0.4456 (8) | −0.0287 (4) | 0.026 (3) | |
C25 | 0.2586 (12) | 0.5368 (8) | −0.0094 (4) | 0.028 (3) | |
C26 | 0.1611 (13) | 0.5315 (8) | 0.0346 (4) | 0.033 (3) | |
C27 | 0.1298 (13) | 0.4311 (9) | 0.0604 (4) | 0.029 (3) | |
C28 | 0.4294 (16) | 0.4527 (10) | −0.0717 (5) | 0.048 (3) | |
H28 | 0.4780 | 0.3921 | −0.0855 | 0.057* | |
C29 | 0.4586 (13) | 0.5484 (10) | −0.0946 (4) | 0.037 (3) | |
H29 | 0.5264 | 0.5523 | −0.1240 | 0.045* | |
C30 | 0.3912 (15) | 0.6357 (10) | −0.0752 (5) | 0.045 (3) | |
H30 | 0.4146 | 0.7000 | −0.0908 | 0.054* | |
C31 | 0.2868 (14) | 0.6327 (9) | −0.0323 (4) | 0.038 (3) | |
C32 | 0.2127 (16) | 0.7209 (10) | −0.0108 (5) | 0.048 (3) | |
H32 | 0.2313 | 0.7864 | −0.0261 | 0.058* | |
C33 | 0.1164 (16) | 0.7152 (10) | 0.0308 (6) | 0.052 (4) | |
H33 | 0.0679 | 0.7761 | 0.0445 | 0.063* | |
C34 | 0.0875 (15) | 0.6188 (9) | 0.0542 (5) | 0.041 (3) | |
H34 | 0.0179 | 0.6142 | 0.0831 | 0.049* | |
C35 | 0.0854 (14) | 0.6949 (9) | 0.3646 (4) | 0.034 (3) | |
C36 | 0.1447 (15) | 0.7941 (10) | 0.3643 (5) | 0.050 (4) | |
C37 | 0.2148 (15) | 0.8225 (10) | 0.4097 (5) | 0.047 (3) | |
C38 | 0.2327 (14) | 0.7556 (10) | 0.4551 (5) | 0.041 (3) | |
C39 | 0.1762 (15) | 0.6566 (9) | 0.4570 (5) | 0.038 (3) | |
C40 | 0.1352 (17) | 0.8589 (12) | 0.3191 (6) | 0.066 (4) | |
H40 | 0.0910 | 0.8389 | 0.2883 | 0.080* | |
C41 | 0.193 (2) | 0.9567 (13) | 0.3196 (8) | 0.079 (6) | |
H41 | 0.1857 | 1.0024 | 0.2891 | 0.095* | |
C42 | 0.259 (2) | 0.9846 (13) | 0.3636 (9) | 0.093 (7) | |
H42 | 0.2978 | 1.0495 | 0.3631 | 0.111* | |
C43 | 0.2719 (18) | 0.9198 (12) | 0.4095 (7) | 0.067 (5) | |
C44 | 0.338 (2) | 0.9462 (14) | 0.4554 (10) | 0.097 (7) | |
H44 | 0.3774 | 1.0107 | 0.4560 | 0.116* | |
C45 | 0.347 (2) | 0.8822 (17) | 0.4981 (8) | 0.102 (8) | |
H45 | 0.3886 | 0.9037 | 0.5290 | 0.123* | |
C46 | 0.2971 (19) | 0.7845 (13) | 0.4997 (6) | 0.074 (5) | |
H46 | 0.3075 | 0.7395 | 0.5305 | 0.089* | |
C47 | 1.1097 (13) | 0.4317 (9) | 0.2545 (5) | 0.041 (3) | |
H47A | 1.0925 | 0.4846 | 0.2795 | 0.049* | |
H47B | 1.1754 | 0.3715 | 0.2725 | 0.049* | |
C48 | 1.2075 (14) | 0.4720 (10) | 0.2117 (5) | 0.046 (3) | |
H48A | 1.1459 | 0.5333 | 0.1932 | 0.056* | |
H48B | 1.2312 | 0.4195 | 0.1866 | 0.056* | |
C49 | 1.3647 (15) | 0.5002 (11) | 0.2325 (5) | 0.057 (4) | |
H49A | 1.3413 | 0.5473 | 0.2596 | 0.086* | |
H49B | 1.4228 | 0.5336 | 0.2043 | 0.086* | |
H49C | 1.4314 | 0.4381 | 0.2471 | 0.086* | |
C50 | 0.9753 (14) | 0.3055 (9) | 0.2120 (4) | 0.040 (3) | |
H50A | 1.0320 | 0.3245 | 0.1796 | 0.048* | |
H50B | 1.0489 | 0.2527 | 0.2326 | 0.048* | |
C51 | 0.8301 (15) | 0.2586 (10) | 0.1978 (5) | 0.050 (4) | |
H51A | 0.7642 | 0.2480 | 0.2292 | 0.060* | |
H51B | 0.7642 | 0.3066 | 0.1724 | 0.060* | |
C52 | 0.8703 (14) | 0.1590 (9) | 0.1752 (5) | 0.043 (3) | |
H52A | 0.9417 | 0.1679 | 0.1455 | 0.064* | |
H52B | 0.7709 | 0.1348 | 0.1637 | 0.064* | |
H52C | 0.9250 | 0.1087 | 0.2015 | 0.064* | |
C53 | 0.8620 (16) | 0.3746 (11) | 0.2938 (5) | 0.055 (4) | |
H53A | 0.8674 | 0.4319 | 0.3157 | 0.066* | |
H53B | 0.7466 | 0.3716 | 0.2861 | 0.066* | |
C54 | 0.9255 (18) | 0.2791 (11) | 0.3240 (5) | 0.062 (4) | |
H54A | 1.0443 | 0.2750 | 0.3272 | 0.074* | |
H54B | 0.8999 | 0.2197 | 0.3061 | 0.074* | |
C55 | 0.8498 (18) | 0.2755 (12) | 0.3786 (5) | 0.068 (5) | |
H55A | 0.8875 | 0.3287 | 0.3981 | 0.103* | |
H55B | 0.8820 | 0.2081 | 0.3971 | 0.103* | |
H55C | 0.7319 | 0.2873 | 0.3753 | 0.103* | |
C56 | 0.8437 (14) | 0.4829 (9) | 0.2098 (5) | 0.045 (3) | |
H56A | 0.8927 | 0.4901 | 0.1750 | 0.054* | |
H56B | 0.7362 | 0.4604 | 0.2053 | 0.054* | |
C57 | 0.8208 (16) | 0.5858 (11) | 0.2304 (6) | 0.063 (4) | |
H57A | 0.9269 | 0.6053 | 0.2398 | 0.075* | |
H57B | 0.7543 | 0.5829 | 0.2620 | 0.075* | |
C58 | 0.7370 (17) | 0.6671 (10) | 0.1895 (5) | 0.058 (4) | |
H58A | 0.8101 | 0.6776 | 0.1604 | 0.086* | |
H58B | 0.7092 | 0.7318 | 0.2053 | 0.086* | |
H58C | 0.6385 | 0.6435 | 0.1769 | 0.086* | |
N1 | 0.7007 (11) | −0.0794 (7) | 0.3238 (3) | 0.034 (2) | |
N2 | 0.2092 (10) | 0.3442 (6) | 0.0410 (3) | 0.026 (2) | |
N3 | 0.0984 (11) | 0.6332 (7) | 0.4115 (4) | 0.038 (2) | |
N4 | 0.9467 (9) | 0.3998 (7) | 0.2425 (3) | 0.029 (2) | |
O1 | 0.5616 (10) | −0.1524 (7) | 0.2649 (3) | 0.057 (2) | |
O2 | 0.8241 (10) | 0.0028 (7) | 0.3822 (3) | 0.052 (2) | |
O3 | 0.3647 (10) | 0.2645 (6) | −0.0194 (3) | 0.044 (2) | |
O4 | 0.0420 (9) | 0.4228 (6) | 0.0977 (3) | 0.044 (2) | |
O5 | 0.0258 (11) | 0.6650 (7) | 0.3267 (3) | 0.058 (3) | |
O6 | 0.1929 (11) | 0.5924 (7) | 0.4929 (4) | 0.058 (2) | |
C59 | 0.3083 (17) | 0.8385 (10) | 0.1729 (5) | 0.057 (4) | |
D59 | 0.3931 | 0.8244 | 0.2007 | 0.068* | |
Cl1 | 0.2370 (6) | 0.9668 (3) | 0.16862 (18) | 0.0853 (13) | |
Cl2 | 0.3958 (5) | 0.8048 (3) | 0.11355 (14) | 0.0670 (10) | |
Cl3 | 0.1562 (7) | 0.7629 (3) | 0.1883 (2) | 0.1041 (17) | |
C60 | 0.6985 (15) | 0.9561 (10) | 0.0572 (5) | 0.053 (4) | |
D60 | 0.6359 | 0.8989 | 0.0500 | 0.064* | |
Cl4 | 0.8450 (7) | 0.9094 (4) | 0.1027 (2) | 0.118 (2) | |
Cl5 | 0.5647 (4) | 1.0526 (3) | 0.08359 (18) | 0.0742 (12) | |
Cl6 | 0.7771 (7) | 1.0014 (3) | −0.00006 (18) | 0.1005 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.0275 (3) | 0.0295 (3) | 0.0336 (3) | −0.0033 (2) | 0.0002 (2) | 0.0036 (2) |
Au2 | 0.0422 (3) | 0.0298 (3) | 0.0332 (3) | −0.0041 (2) | −0.0039 (2) | −0.0017 (2) |
C1 | 0.028 (7) | 0.053 (9) | 0.028 (7) | −0.011 (6) | −0.009 (6) | 0.010 (6) |
C2 | 0.030 (7) | 0.041 (8) | 0.019 (6) | 0.001 (6) | 0.004 (5) | 0.010 (5) |
C3 | 0.036 (7) | 0.046 (8) | 0.038 (7) | 0.001 (6) | 0.010 (6) | 0.012 (6) |
C4 | 0.016 (6) | 0.029 (7) | 0.046 (8) | 0.003 (5) | 0.006 (6) | −0.006 (6) |
C5 | 0.026 (7) | 0.030 (7) | 0.035 (7) | 0.002 (5) | 0.007 (6) | −0.003 (5) |
C6 | 0.043 (8) | 0.034 (7) | 0.031 (7) | −0.011 (6) | −0.009 (6) | 0.007 (5) |
C7 | 0.043 (8) | 0.038 (8) | 0.032 (7) | −0.012 (6) | 0.005 (6) | −0.001 (6) |
C8 | 0.050 (9) | 0.037 (8) | 0.048 (8) | −0.021 (7) | 0.009 (7) | −0.008 (6) |
C9 | 0.044 (8) | 0.027 (7) | 0.049 (8) | −0.015 (6) | 0.005 (6) | −0.014 (6) |
C11 | 0.033 (7) | 0.042 (8) | 0.027 (7) | 0.003 (6) | −0.007 (6) | −0.008 (6) |
C12 | 0.029 (7) | 0.037 (8) | 0.043 (8) | −0.003 (6) | −0.001 (6) | −0.018 (6) |
C13 | 0.041 (7) | 0.036 (8) | 0.031 (7) | 0.005 (6) | 0.005 (6) | −0.006 (6) |
C14 | 0.028 (7) | 0.041 (8) | 0.035 (7) | −0.006 (6) | −0.006 (6) | −0.006 (6) |
C15 | 0.031 (7) | 0.038 (8) | 0.033 (7) | 0.006 (6) | −0.002 (6) | 0.003 (6) |
C16 | 0.038 (8) | 0.047 (9) | 0.064 (9) | 0.001 (7) | 0.013 (7) | −0.010 (7) |
C17 | 0.044 (9) | 0.060 (10) | 0.064 (10) | −0.025 (7) | 0.022 (8) | −0.017 (8) |
C18 | 0.051 (9) | 0.031 (8) | 0.075 (11) | 0.007 (7) | 0.023 (8) | 0.013 (7) |
C19 | 0.055 (9) | 0.033 (8) | 0.047 (9) | −0.001 (6) | 0.016 (7) | 0.002 (6) |
C20 | 0.066 (10) | 0.051 (10) | 0.047 (9) | 0.006 (8) | 0.012 (8) | 0.011 (7) |
C21 | 0.065 (10) | 0.043 (9) | 0.045 (8) | −0.009 (7) | 0.003 (7) | 0.009 (7) |
C22 | 0.051 (9) | 0.054 (9) | 0.048 (9) | 0.002 (7) | −0.001 (7) | −0.004 (7) |
C23 | 0.025 (6) | 0.028 (7) | 0.032 (7) | −0.010 (5) | −0.005 (5) | −0.002 (5) |
C24 | 0.032 (7) | 0.032 (7) | 0.013 (6) | −0.012 (5) | −0.002 (5) | 0.004 (5) |
C25 | 0.023 (6) | 0.038 (7) | 0.023 (6) | −0.010 (5) | −0.005 (5) | −0.003 (5) |
C26 | 0.028 (7) | 0.031 (7) | 0.039 (7) | −0.002 (5) | −0.013 (6) | −0.007 (5) |
C27 | 0.019 (6) | 0.041 (8) | 0.029 (7) | −0.007 (5) | −0.012 (5) | −0.002 (5) |
C28 | 0.052 (9) | 0.058 (9) | 0.034 (7) | −0.009 (7) | −0.014 (6) | −0.006 (6) |
C29 | 0.027 (7) | 0.056 (9) | 0.031 (7) | −0.018 (6) | −0.005 (5) | 0.009 (6) |
C30 | 0.051 (8) | 0.039 (8) | 0.045 (8) | −0.023 (7) | −0.010 (7) | 0.015 (6) |
C31 | 0.040 (8) | 0.038 (8) | 0.033 (7) | −0.001 (6) | −0.018 (6) | 0.010 (6) |
C32 | 0.046 (8) | 0.041 (9) | 0.059 (9) | −0.015 (7) | −0.025 (7) | 0.003 (7) |
C33 | 0.050 (9) | 0.033 (8) | 0.075 (10) | 0.003 (6) | −0.014 (8) | −0.025 (7) |
C34 | 0.048 (8) | 0.032 (8) | 0.043 (8) | −0.002 (6) | −0.007 (6) | −0.011 (6) |
C35 | 0.032 (7) | 0.036 (8) | 0.031 (7) | 0.008 (6) | 0.007 (6) | −0.001 (6) |
C36 | 0.046 (8) | 0.048 (9) | 0.051 (9) | 0.010 (7) | 0.032 (7) | 0.007 (7) |
C37 | 0.043 (8) | 0.040 (8) | 0.060 (10) | −0.009 (6) | 0.027 (7) | −0.020 (7) |
C38 | 0.038 (8) | 0.052 (9) | 0.036 (8) | −0.010 (6) | 0.010 (6) | −0.019 (6) |
C39 | 0.057 (9) | 0.025 (7) | 0.031 (7) | −0.001 (6) | 0.010 (6) | 0.001 (6) |
C40 | 0.051 (9) | 0.064 (11) | 0.074 (11) | 0.017 (8) | 0.027 (8) | 0.014 (8) |
C41 | 0.073 (12) | 0.061 (12) | 0.095 (14) | 0.008 (9) | 0.054 (11) | 0.024 (10) |
C42 | 0.090 (15) | 0.051 (11) | 0.140 (19) | −0.019 (10) | 0.072 (14) | −0.011 (13) |
C43 | 0.056 (10) | 0.051 (10) | 0.100 (13) | −0.014 (8) | 0.048 (10) | −0.023 (10) |
C44 | 0.089 (14) | 0.072 (13) | 0.15 (2) | −0.066 (11) | 0.046 (14) | −0.060 (14) |
C45 | 0.111 (16) | 0.124 (18) | 0.101 (16) | −0.086 (14) | 0.058 (13) | −0.071 (14) |
C46 | 0.081 (12) | 0.104 (14) | 0.049 (10) | −0.041 (10) | 0.018 (8) | −0.034 (9) |
C47 | 0.021 (7) | 0.049 (8) | 0.052 (8) | −0.005 (6) | −0.002 (6) | 0.002 (6) |
C48 | 0.039 (8) | 0.048 (8) | 0.052 (8) | −0.007 (6) | 0.003 (6) | 0.003 (6) |
C49 | 0.040 (8) | 0.083 (11) | 0.054 (9) | −0.034 (7) | 0.001 (7) | 0.000 (7) |
C50 | 0.043 (8) | 0.040 (8) | 0.040 (7) | −0.015 (6) | 0.003 (6) | −0.004 (6) |
C51 | 0.041 (8) | 0.070 (10) | 0.039 (8) | −0.009 (7) | 0.007 (6) | −0.003 (7) |
C52 | 0.043 (8) | 0.047 (8) | 0.043 (8) | −0.012 (6) | 0.009 (6) | −0.013 (6) |
C53 | 0.049 (9) | 0.066 (10) | 0.050 (9) | −0.004 (7) | −0.002 (7) | −0.014 (7) |
C54 | 0.076 (11) | 0.083 (11) | 0.032 (8) | −0.035 (9) | 0.007 (7) | −0.004 (7) |
C55 | 0.089 (12) | 0.102 (13) | 0.031 (8) | −0.068 (10) | 0.017 (8) | −0.017 (7) |
C56 | 0.021 (7) | 0.054 (9) | 0.062 (9) | −0.009 (6) | −0.006 (6) | −0.006 (7) |
C57 | 0.035 (8) | 0.078 (11) | 0.079 (11) | 0.001 (7) | 0.003 (7) | −0.034 (9) |
C58 | 0.067 (10) | 0.038 (8) | 0.069 (10) | −0.008 (7) | −0.001 (8) | −0.014 (7) |
N1 | 0.034 (6) | 0.036 (6) | 0.028 (6) | 0.005 (5) | 0.007 (5) | −0.001 (4) |
N2 | 0.030 (5) | 0.027 (5) | 0.023 (5) | −0.004 (4) | −0.005 (4) | −0.004 (4) |
N3 | 0.039 (6) | 0.030 (6) | 0.045 (6) | −0.004 (5) | 0.011 (5) | −0.010 (5) |
N4 | 0.011 (5) | 0.047 (6) | 0.030 (5) | −0.006 (4) | 0.001 (4) | 0.002 (4) |
O1 | 0.047 (6) | 0.070 (7) | 0.051 (6) | 0.003 (5) | −0.005 (5) | −0.009 (5) |
O2 | 0.050 (6) | 0.038 (6) | 0.068 (6) | −0.005 (5) | −0.005 (5) | −0.008 (5) |
O3 | 0.058 (6) | 0.027 (5) | 0.047 (5) | −0.006 (4) | 0.008 (4) | −0.009 (4) |
O4 | 0.037 (5) | 0.059 (6) | 0.035 (5) | −0.007 (4) | 0.005 (4) | 0.004 (4) |
O5 | 0.066 (7) | 0.066 (7) | 0.045 (6) | −0.008 (5) | −0.014 (5) | −0.012 (5) |
O6 | 0.062 (6) | 0.057 (6) | 0.057 (6) | −0.001 (5) | −0.001 (5) | −0.013 (5) |
C59 | 0.060 (10) | 0.059 (10) | 0.049 (9) | 0.008 (7) | −0.019 (7) | −0.008 (7) |
Cl1 | 0.109 (4) | 0.040 (2) | 0.105 (3) | 0.002 (2) | 0.020 (3) | −0.008 (2) |
Cl2 | 0.079 (3) | 0.056 (2) | 0.067 (2) | −0.008 (2) | −0.005 (2) | −0.0153 (18) |
Cl3 | 0.139 (4) | 0.071 (3) | 0.113 (4) | −0.055 (3) | 0.029 (3) | −0.014 (3) |
C60 | 0.046 (8) | 0.039 (8) | 0.078 (10) | −0.012 (6) | −0.013 (7) | −0.018 (7) |
Cl4 | 0.121 (4) | 0.111 (4) | 0.110 (4) | 0.060 (3) | −0.046 (3) | −0.041 (3) |
Cl5 | 0.047 (2) | 0.044 (2) | 0.133 (4) | −0.0038 (17) | 0.009 (2) | −0.020 (2) |
Cl6 | 0.157 (5) | 0.059 (3) | 0.097 (3) | −0.046 (3) | 0.042 (3) | −0.028 (2) |
Au1—C4 | 1.985 (13) | C35—C36 | 1.455 (18) |
Au1—C2 | 2.200 (10) | C36—C40 | 1.383 (17) |
Au1—C1 | 2.232 (11) | C36—C37 | 1.412 (18) |
Au1—Au2 | 3.4507 (6) | C37—C38 | 1.404 (17) |
Au2—C1 | 2.005 (13) | C37—C43 | 1.423 (19) |
Au2—C7 | 2.009 (13) | C38—C46 | 1.376 (17) |
C1—C2 | 1.195 (15) | C38—C39 | 1.440 (16) |
C2—C3 | 1.482 (16) | C39—O6 | 1.198 (13) |
C3—N1 | 1.458 (13) | C39—N3 | 1.419 (15) |
C3—H3A | 0.9900 | C40—C41 | 1.43 (2) |
C3—H3B | 0.9900 | C40—H40 | 0.9500 |
C4—C5 | 1.192 (15) | C41—C42 | 1.36 (2) |
C5—C6 | 1.455 (16) | C41—H41 | 0.9500 |
C6—N2 | 1.477 (13) | C42—C43 | 1.40 (2) |
C6—H6A | 0.9900 | C42—H42 | 0.9500 |
C6—H6B | 0.9900 | C43—C44 | 1.40 (2) |
C7—C8 | 1.199 (16) | C44—C45 | 1.33 (3) |
C8—C9 | 1.497 (17) | C44—H44 | 0.9500 |
C9—N3 | 1.490 (14) | C45—C46 | 1.40 (2) |
C9—H9A | 0.9900 | C45—H45 | 0.9500 |
C9—H9B | 0.9900 | C46—H46 | 0.9500 |
C11—O1 | 1.220 (12) | C47—C48 | 1.476 (15) |
C11—N1 | 1.416 (15) | C47—N4 | 1.513 (13) |
C11—C12 | 1.439 (16) | C47—H47A | 0.9900 |
C12—C16 | 1.370 (17) | C47—H47B | 0.9900 |
C12—C13 | 1.406 (16) | C48—C49 | 1.519 (16) |
C13—C14 | 1.395 (16) | C48—H48A | 0.9900 |
C13—C19 | 1.423 (16) | C48—H48B | 0.9900 |
C14—C22 | 1.369 (16) | C49—H49A | 0.9800 |
C14—C15 | 1.490 (16) | C49—H49B | 0.9800 |
C15—O2 | 1.225 (14) | C49—H49C | 0.9800 |
C15—N1 | 1.374 (14) | C50—C51 | 1.487 (16) |
C16—C17 | 1.396 (18) | C50—N4 | 1.524 (14) |
C16—H16 | 0.9500 | C50—H50A | 0.9900 |
C17—C18 | 1.371 (18) | C50—H50B | 0.9900 |
C17—H17 | 0.9500 | C51—C52 | 1.484 (16) |
C18—C19 | 1.402 (18) | C51—H51A | 0.9900 |
C18—H18 | 0.9500 | C51—H51B | 0.9900 |
C19—C20 | 1.415 (18) | C52—H52A | 0.9800 |
C20—C21 | 1.352 (18) | C52—H52B | 0.9800 |
C20—H20 | 0.9500 | C52—H52C | 0.9800 |
C21—C22 | 1.428 (17) | C53—C54 | 1.467 (18) |
C21—H21 | 0.9500 | C53—N4 | 1.533 (15) |
C22—H22 | 0.9500 | C53—H53A | 0.9900 |
C23—O3 | 1.204 (12) | C53—H53B | 0.9900 |
C23—N2 | 1.401 (13) | C54—C55 | 1.547 (17) |
C23—C24 | 1.486 (14) | C54—H54A | 0.9900 |
C24—C28 | 1.395 (15) | C54—H54B | 0.9900 |
C24—C25 | 1.405 (14) | C55—H55A | 0.9800 |
C25—C31 | 1.398 (15) | C55—H55B | 0.9800 |
C25—C26 | 1.400 (15) | C55—H55C | 0.9800 |
C26—C34 | 1.374 (15) | C56—C57 | 1.490 (17) |
C26—C27 | 1.484 (15) | C56—N4 | 1.506 (14) |
C27—O4 | 1.217 (12) | C56—H56A | 0.9900 |
C27—N2 | 1.384 (13) | C56—H56B | 0.9900 |
C28—C29 | 1.398 (16) | C57—C58 | 1.543 (18) |
C28—H28 | 0.9500 | C57—H57A | 0.9900 |
C29—C30 | 1.354 (16) | C57—H57B | 0.9900 |
C29—H29 | 0.9500 | C58—H58A | 0.9800 |
C30—C31 | 1.412 (16) | C58—H58B | 0.9800 |
C30—H30 | 0.9500 | C58—H58C | 0.9800 |
C31—C32 | 1.407 (17) | C59—Cl1 | 1.719 (13) |
C32—C33 | 1.346 (17) | C59—Cl3 | 1.734 (15) |
C32—H32 | 0.9500 | C59—Cl2 | 1.767 (13) |
C33—C34 | 1.409 (17) | C59—D59 | 1.0000 |
C33—H33 | 0.9500 | C60—Cl6 | 1.711 (14) |
C34—H34 | 0.9500 | C60—Cl4 | 1.720 (13) |
C35—O5 | 1.215 (13) | C60—Cl5 | 1.769 (13) |
C35—N3 | 1.400 (14) | C60—D60 | 1.0000 |
C4—Au1—C2 | 162.3 (4) | O6—C39—C38 | 125.7 (12) |
C4—Au1—C1 | 166.5 (4) | N3—C39—C38 | 116.2 (10) |
C2—Au1—C1 | 31.3 (4) | C36—C40—C41 | 118.9 (16) |
C4—Au1—Au2 | 133.1 (3) | C36—C40—H40 | 120.5 |
C2—Au1—Au2 | 64.6 (3) | C41—C40—H40 | 120.5 |
C1—Au1—Au2 | 33.3 (3) | C42—C41—C40 | 120.5 (16) |
C1—Au2—C7 | 177.5 (5) | C42—C41—H41 | 119.7 |
C1—Au2—Au1 | 37.7 (3) | C40—C41—H41 | 119.7 |
C7—Au2—Au1 | 140.1 (3) | C41—C42—C43 | 121.5 (17) |
C2—C1—Au2 | 177.8 (10) | C41—C42—H42 | 119.3 |
C2—C1—Au1 | 72.8 (7) | C43—C42—H42 | 119.3 |
Au2—C1—Au1 | 108.9 (5) | C44—C43—C42 | 122.9 (18) |
C1—C2—C3 | 162.0 (11) | C44—C43—C37 | 118.4 (16) |
C1—C2—Au1 | 75.9 (7) | C42—C43—C37 | 118.7 (17) |
C3—C2—Au1 | 122.1 (8) | C45—C44—C43 | 120.8 (16) |
N1—C3—C2 | 111.9 (9) | C45—C44—H44 | 119.6 |
N1—C3—H3A | 109.2 | C43—C44—H44 | 119.6 |
C2—C3—H3A | 109.2 | C44—C45—C46 | 122.8 (18) |
N1—C3—H3B | 109.2 | C44—C45—H45 | 118.6 |
C2—C3—H3B | 109.2 | C46—C45—H45 | 118.6 |
H3A—C3—H3B | 107.9 | C38—C46—C45 | 117.9 (16) |
C5—C4—Au1 | 177.2 (10) | C38—C46—H46 | 121.1 |
C4—C5—C6 | 176.5 (12) | C45—C46—H46 | 121.1 |
C5—C6—N2 | 112.9 (9) | C48—C47—N4 | 119.4 (10) |
C5—C6—H6A | 109.0 | C48—C47—H47A | 107.5 |
N2—C6—H6A | 109.0 | N4—C47—H47A | 107.5 |
C5—C6—H6B | 109.0 | C48—C47—H47B | 107.5 |
N2—C6—H6B | 109.0 | N4—C47—H47B | 107.5 |
H6A—C6—H6B | 107.8 | H47A—C47—H47B | 107.0 |
C8—C7—Au2 | 170.6 (11) | C47—C48—C49 | 110.5 (10) |
C7—C8—C9 | 178.6 (14) | C47—C48—H48A | 109.6 |
N3—C9—C8 | 110.1 (9) | C49—C48—H48A | 109.6 |
N3—C9—H9A | 109.6 | C47—C48—H48B | 109.6 |
C8—C9—H9A | 109.6 | C49—C48—H48B | 109.6 |
N3—C9—H9B | 109.6 | H48A—C48—H48B | 108.1 |
C8—C9—H9B | 109.6 | C48—C49—H49A | 109.5 |
H9A—C9—H9B | 108.2 | C48—C49—H49B | 109.5 |
O1—C11—N1 | 118.2 (11) | H49A—C49—H49B | 109.5 |
O1—C11—C12 | 125.1 (11) | C48—C49—H49C | 109.5 |
N1—C11—C12 | 116.7 (10) | H49A—C49—H49C | 109.5 |
C16—C12—C13 | 120.4 (12) | H49B—C49—H49C | 109.5 |
C16—C12—C11 | 118.7 (11) | C51—C50—N4 | 116.7 (10) |
C13—C12—C11 | 120.8 (11) | C51—C50—H50A | 108.1 |
C14—C13—C12 | 120.7 (11) | N4—C50—H50A | 108.1 |
C14—C13—C19 | 120.3 (11) | C51—C50—H50B | 108.1 |
C12—C13—C19 | 119.0 (12) | N4—C50—H50B | 108.1 |
C22—C14—C13 | 121.1 (11) | H50A—C50—H50B | 107.3 |
C22—C14—C15 | 118.7 (11) | C52—C51—C50 | 113.0 (10) |
C13—C14—C15 | 120.2 (11) | C52—C51—H51A | 109.0 |
O2—C15—N1 | 120.2 (11) | C50—C51—H51A | 109.0 |
O2—C15—C14 | 123.7 (11) | C52—C51—H51B | 109.0 |
N1—C15—C14 | 116.1 (11) | C50—C51—H51B | 109.0 |
C12—C16—C17 | 120.5 (13) | H51A—C51—H51B | 107.8 |
C12—C16—H16 | 119.8 | C51—C52—H52A | 109.5 |
C17—C16—H16 | 119.8 | C51—C52—H52B | 109.5 |
C18—C17—C16 | 120.6 (13) | H52A—C52—H52B | 109.5 |
C18—C17—H17 | 119.7 | C51—C52—H52C | 109.5 |
C16—C17—H17 | 119.7 | H52A—C52—H52C | 109.5 |
C17—C18—C19 | 120.4 (12) | H52B—C52—H52C | 109.5 |
C17—C18—H18 | 119.8 | C54—C53—N4 | 116.6 (11) |
C19—C18—H18 | 119.8 | C54—C53—H53A | 108.1 |
C18—C19—C20 | 123.6 (12) | N4—C53—H53A | 108.1 |
C18—C19—C13 | 119.2 (12) | C54—C53—H53B | 108.1 |
C20—C19—C13 | 117.3 (12) | N4—C53—H53B | 108.1 |
C21—C20—C19 | 122.0 (12) | H53A—C53—H53B | 107.3 |
C21—C20—H20 | 119.0 | C53—C54—C55 | 109.9 (13) |
C19—C20—H20 | 119.0 | C53—C54—H54A | 109.7 |
C20—C21—C22 | 120.3 (13) | C55—C54—H54A | 109.7 |
C20—C21—H21 | 119.9 | C53—C54—H54B | 109.7 |
C22—C21—H21 | 119.9 | C55—C54—H54B | 109.7 |
C14—C22—C21 | 119.1 (13) | H54A—C54—H54B | 108.2 |
C14—C22—H22 | 120.4 | C54—C55—H55A | 109.5 |
C21—C22—H22 | 120.4 | C54—C55—H55B | 109.5 |
O3—C23—N2 | 121.8 (10) | H55A—C55—H55B | 109.5 |
O3—C23—C24 | 122.7 (10) | C54—C55—H55C | 109.5 |
N2—C23—C24 | 115.5 (9) | H55A—C55—H55C | 109.5 |
C28—C24—C25 | 118.3 (10) | H55B—C55—H55C | 109.5 |
C28—C24—C23 | 119.8 (10) | C57—C56—N4 | 116.1 (11) |
C25—C24—C23 | 121.9 (9) | C57—C56—H56A | 108.3 |
C31—C25—C26 | 119.2 (10) | N4—C56—H56A | 108.3 |
C31—C25—C24 | 121.5 (10) | C57—C56—H56B | 108.3 |
C26—C25—C24 | 119.3 (10) | N4—C56—H56B | 108.3 |
C34—C26—C25 | 121.1 (11) | H56A—C56—H56B | 107.4 |
C34—C26—C27 | 118.0 (11) | C56—C57—C58 | 110.7 (11) |
C25—C26—C27 | 120.8 (10) | C56—C57—H57A | 109.5 |
O4—C27—N2 | 119.9 (10) | C58—C57—H57A | 109.5 |
O4—C27—C26 | 123.1 (10) | C56—C57—H57B | 109.5 |
N2—C27—C26 | 117.0 (10) | C58—C57—H57B | 109.5 |
C24—C28—C29 | 120.5 (12) | H57A—C57—H57B | 108.1 |
C24—C28—H28 | 119.8 | C57—C58—H58A | 109.5 |
C29—C28—H28 | 119.8 | C57—C58—H58B | 109.5 |
C30—C29—C28 | 120.6 (11) | H58A—C58—H58B | 109.5 |
C30—C29—H29 | 119.7 | C57—C58—H58C | 109.5 |
C28—C29—H29 | 119.7 | H58A—C58—H58C | 109.5 |
C29—C30—C31 | 121.1 (11) | H58B—C58—H58C | 109.5 |
C29—C30—H30 | 119.4 | C15—N1—C11 | 125.3 (10) |
C31—C30—H30 | 119.4 | C15—N1—C3 | 117.3 (10) |
C25—C31—C32 | 118.4 (11) | C11—N1—C3 | 117.3 (10) |
C25—C31—C30 | 118.0 (11) | C27—N2—C23 | 125.3 (9) |
C32—C31—C30 | 123.6 (11) | C27—N2—C6 | 117.6 (9) |
C33—C32—C31 | 122.0 (12) | C23—N2—C6 | 117.0 (9) |
C33—C32—H32 | 119.0 | C35—N3—C39 | 125.0 (10) |
C31—C32—H32 | 119.0 | C35—N3—C9 | 116.8 (10) |
C32—C33—C34 | 119.9 (12) | C39—N3—C9 | 118.1 (9) |
C32—C33—H33 | 120.1 | C56—N4—C47 | 111.5 (9) |
C34—C33—H33 | 120.1 | C56—N4—C50 | 108.3 (9) |
C26—C34—C33 | 119.3 (12) | C47—N4—C50 | 107.7 (8) |
C26—C34—H34 | 120.4 | C56—N4—C53 | 110.0 (9) |
C33—C34—H34 | 120.4 | C47—N4—C53 | 108.7 (9) |
O5—C35—N3 | 120.0 (12) | C50—N4—C53 | 110.6 (9) |
O5—C35—C36 | 123.2 (11) | Cl1—C59—Cl3 | 111.7 (8) |
N3—C35—C36 | 116.7 (11) | Cl1—C59—Cl2 | 110.3 (7) |
C40—C36—C37 | 120.6 (14) | Cl3—C59—Cl2 | 109.0 (8) |
C40—C36—C35 | 119.7 (14) | Cl1—C59—D59 | 108.6 |
C37—C36—C35 | 119.7 (11) | Cl3—C59—D59 | 108.6 |
C38—C37—C36 | 121.3 (12) | Cl2—C59—D59 | 108.6 |
C38—C37—C43 | 118.9 (14) | Cl6—C60—Cl4 | 112.6 (8) |
C36—C37—C43 | 119.8 (14) | Cl6—C60—Cl5 | 111.1 (7) |
C46—C38—C37 | 121.2 (13) | Cl4—C60—Cl5 | 108.8 (7) |
C46—C38—C39 | 118.0 (13) | Cl6—C60—D60 | 108.1 |
C37—C38—C39 | 120.8 (11) | Cl4—C60—D60 | 108.1 |
O6—C39—N3 | 118.1 (11) | Cl5—C60—D60 | 108.1 |
C4—Au1—Au2—C1 | −179.4 (7) | C25—C26—C34—C33 | −2.7 (17) |
C2—Au1—Au2—C1 | 0.7 (6) | C27—C26—C34—C33 | 179.3 (10) |
C4—Au1—Au2—C7 | 2.6 (7) | C32—C33—C34—C26 | 1.3 (18) |
C2—Au1—Au2—C7 | −177.3 (6) | O5—C35—C36—C40 | −0.4 (18) |
C1—Au1—Au2—C7 | −178.0 (7) | N3—C35—C36—C40 | −179.9 (10) |
C4—Au1—C1—C2 | −179.3 (16) | O5—C35—C36—C37 | −179.0 (11) |
Au2—Au1—C1—C2 | 178.7 (11) | N3—C35—C36—C37 | 1.6 (16) |
C2—Au1—C1—Au2 | −178.7 (11) | C40—C36—C37—C38 | −176.8 (11) |
C4—Au1—C2—C1 | 179.5 (12) | C35—C36—C37—C38 | 1.7 (17) |
Au2—Au1—C2—C1 | −0.8 (7) | C40—C36—C37—C43 | 1.9 (18) |
C1—Au1—C2—C3 | 179.1 (14) | C35—C36—C37—C43 | −179.6 (11) |
Au2—Au1—C2—C3 | 178.3 (10) | C36—C37—C38—C46 | −178.3 (12) |
Au1—C2—C3—N1 | −127.9 (9) | C43—C37—C38—C46 | 3.1 (18) |
O1—C11—C12—C16 | 2.1 (18) | C36—C37—C38—C39 | −1.5 (18) |
N1—C11—C12—C16 | −177.3 (10) | C43—C37—C38—C39 | 179.8 (11) |
O1—C11—C12—C13 | −179.7 (11) | C46—C38—C39—O6 | −7.0 (19) |
N1—C11—C12—C13 | 0.9 (15) | C37—C38—C39—O6 | 176.1 (12) |
C16—C12—C13—C14 | 180.0 (11) | C46—C38—C39—N3 | 174.9 (11) |
C11—C12—C13—C14 | 1.8 (17) | C37—C38—C39—N3 | −1.9 (16) |
C16—C12—C13—C19 | −1.2 (17) | C37—C36—C40—C41 | −1.9 (18) |
C11—C12—C13—C19 | −179.4 (10) | C35—C36—C40—C41 | 179.6 (11) |
C12—C13—C14—C22 | 179.4 (11) | C41—C42—C43—C44 | −179.7 (16) |
C19—C13—C14—C22 | 0.6 (17) | C38—C37—C43—C44 | −2.4 (19) |
C12—C13—C14—C15 | −0.9 (17) | C36—C37—C43—C44 | 178.9 (13) |
C19—C13—C14—C15 | −179.7 (10) | C38—C37—C43—C42 | 177.6 (12) |
C22—C14—C15—O2 | −1.1 (17) | C36—C37—C43—C42 | −1.1 (19) |
C13—C14—C15—O2 | 179.2 (11) | C42—C43—C44—C45 | 179.7 (17) |
C22—C14—C15—N1 | 177.1 (10) | C39—C38—C46—C45 | −177.9 (14) |
C13—C14—C15—N1 | −2.6 (15) | N4—C47—C48—C49 | 179.3 (10) |
C13—C12—C16—C17 | 1.2 (18) | N4—C50—C51—C52 | −171.5 (10) |
C11—C12—C16—C17 | 179.4 (11) | N4—C53—C54—C55 | 169.1 (11) |
C12—C16—C17—C18 | −0.7 (19) | N4—C56—C57—C58 | 170.9 (10) |
C16—C17—C18—C19 | 0.2 (19) | O2—C15—N1—C11 | −176.0 (10) |
C17—C18—C19—C20 | −179.6 (12) | C14—C15—N1—C11 | 5.7 (15) |
C17—C18—C19—C13 | −0.2 (18) | O2—C15—N1—C3 | 0.3 (15) |
C14—C13—C19—C18 | 179.5 (11) | C14—C15—N1—C3 | −178.0 (9) |
C12—C13—C19—C18 | 0.7 (17) | O1—C11—N1—C15 | 175.6 (10) |
C14—C13—C19—C20 | −1.0 (17) | C12—C11—N1—C15 | −4.9 (15) |
C12—C13—C19—C20 | −179.8 (11) | O1—C11—N1—C3 | −0.8 (15) |
C18—C19—C20—C21 | −179.3 (13) | C12—C11—N1—C3 | 178.7 (9) |
C13—C19—C20—C21 | 1.2 (19) | C2—C3—N1—C15 | −75.4 (13) |
C19—C20—C21—C22 | −1 (2) | C2—C3—N1—C11 | 101.3 (12) |
C13—C14—C22—C21 | −0.3 (18) | O4—C27—N2—C23 | 176.6 (10) |
C15—C14—C22—C21 | −180.0 (11) | C26—C27—N2—C23 | −5.0 (14) |
C20—C21—C22—C14 | 0.5 (19) | O4—C27—N2—C6 | −3.5 (14) |
O3—C23—C24—C28 | −3.9 (16) | C26—C27—N2—C6 | 174.8 (9) |
N2—C23—C24—C28 | 177.5 (10) | O3—C23—N2—C27 | −175.7 (10) |
O3—C23—C24—C25 | 179.1 (10) | C24—C23—N2—C27 | 2.9 (14) |
N2—C23—C24—C25 | 0.5 (14) | O3—C23—N2—C6 | 4.4 (15) |
C28—C24—C25—C31 | −0.1 (16) | C24—C23—N2—C6 | −177.0 (9) |
C23—C24—C25—C31 | 177.0 (10) | C5—C6—N2—C27 | −70.7 (12) |
C28—C24—C25—C26 | −178.4 (10) | C5—C6—N2—C23 | 109.2 (11) |
C23—C24—C25—C26 | −1.3 (15) | O5—C35—N3—C39 | 175.1 (11) |
C31—C25—C26—C34 | 2.7 (16) | C36—C35—N3—C39 | −5.4 (15) |
C24—C25—C26—C34 | −178.9 (10) | O5—C35—N3—C9 | −1.7 (15) |
C31—C25—C26—C27 | −179.3 (10) | C36—C35—N3—C9 | 177.8 (9) |
C24—C25—C26—C27 | −1.0 (15) | O6—C39—N3—C35 | −172.6 (10) |
C34—C26—C27—O4 | 0.3 (16) | C38—C39—N3—C35 | 5.6 (16) |
C25—C26—C27—O4 | −177.7 (10) | O6—C39—N3—C9 | 4.1 (16) |
C34—C26—C27—N2 | −178.0 (10) | C38—C39—N3—C9 | −177.7 (10) |
C25—C26—C27—N2 | 4.0 (15) | C8—C9—N3—C35 | 87.3 (12) |
C25—C24—C28—C29 | 0.4 (16) | C8—C9—N3—C39 | −89.7 (12) |
C23—C24—C28—C29 | −176.7 (10) | C57—C56—N4—C47 | −53.9 (13) |
C24—C28—C29—C30 | 0.4 (18) | C57—C56—N4—C50 | −172.2 (10) |
C28—C29—C30—C31 | −1.5 (18) | C57—C56—N4—C53 | 66.7 (13) |
C26—C25—C31—C32 | −1.3 (16) | C48—C47—N4—C56 | −51.2 (14) |
C24—C25—C31—C32 | −179.6 (10) | C48—C47—N4—C50 | 67.5 (13) |
C26—C25—C31—C30 | 177.3 (10) | C48—C47—N4—C53 | −172.7 (11) |
C24—C25—C31—C30 | −1.0 (16) | C51—C50—N4—C56 | −61.6 (12) |
C29—C30—C31—C25 | 1.8 (17) | C51—C50—N4—C47 | 177.7 (10) |
C29—C30—C31—C32 | −179.6 (11) | C51—C50—N4—C53 | 59.1 (13) |
C25—C31—C32—C33 | 0.0 (18) | C54—C53—N4—C56 | 165.1 (11) |
C30—C31—C32—C33 | −178.6 (12) | C54—C53—N4—C47 | −72.5 (14) |
C31—C32—C33—C34 | 0.1 (19) | C54—C53—N4—C50 | 45.5 (14) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | (C16H28N)[Au(C14H13N6O)2] | (C12H28N)[Au2(C15H8NO2)3]·2CDCl3 |
Mr | 945.93 | 1523.71 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 150 | 150 |
a, b, c (Å) | 8.4064 (5), 13.3301 (7), 38.100 (2) | 8.3493 (5), 13.1970 (7), 25.8732 (14) |
α, β, γ (°) | 90, 90.651 (1), 90 | 85.084 (1), 89.936 (1), 82.957 (1) |
V (Å3) | 4269.2 (4) | 2818.8 (3) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 3.50 | 5.54 |
Crystal size (mm) | 0.44 × 0.40 × 0.18 | 0.20 × 0.04 × 0.02 |
Data collection | ||
Diffractometer | Bruker SMART APEX CCD area-detector | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.308, 0.572 | 0.750, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37378, 8791, 8217 | 20651, 7339, 5638 |
Rint | 0.027 | 0.064 |
θmax (°) | 26.5 | 22.5 |
(sin θ/λ)max (Å−1) | 0.627 | 0.538 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.065, 1.19 | 0.050, 0.121, 1.03 |
No. of reflections | 8791 | 7339 |
No. of parameters | 509 | 698 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.91, −1.96 | 2.21, −1.07 |
Computer programs: SMART-NT (Bruker, 2001), SAINT-Plus-NT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
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