The cis- and trans-isomers of the polycyclic aromatic compound perinone, C26H12N4O2, form a solid solution (Vat Red 14). This solid solution is isotypic to the crystal structures of cis-perinone (Pigment Red 194) and trans-perinone (Pigment Orange 34) and exhibits a combined positional and orientational disorder: In the crystal, each molecular position is occupied by either a cis- or trans-perinone molecule, both of which have two possible molecular orientations. The structure of cis-perinone exhibits a twofold orientational disorder, whereas the structure of trans-perinone is ordered. The crystal structure of the solid solution was determined by single-crystal X-ray analysis. Extensive lattice-energy minimizations with force-field and DFT-D methods were carried out on combinatorially complete sets of ordered models. For the disordered systems, local structures were calculated, including preferred local arrangements, ordering lengths, and probabilities for the arrangement of neighbouring molecules. The superposition of the atomic positions of all energetically favourable calculated models corresponds well with the experimentally determined crystal structures, explaining not only the atomic positions, but also the site occupancies and anisotropic displacement parameters.
Supporting information
CCDC references: 1470345; 1470346; 1470347
Data collection: SMART V5.628 (BRUKER AXS, 2001) for solid_solution_293K_Cu. Cell refinement: SAINT V6.45 (BRUKER AXS, 2003) for solid_solution_293K_Cu. Data reduction: SAINT V6.45 (BRUKER AXS, 2003) for solid_solution_293K_Cu. Program(s) used to solve structure: L.J. Bourhis et al., in preparation (2013) for solid_solution_100K_Cu; SHELXS97 (Sheldrick, 1990) for solid_solution_293K_Cu, solid_solution_293K_Mo. Program(s) used to refine structure: SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for solid_solution_100K_Cu; SHELXL2013 (Sheldrick, 2013) for solid_solution_293K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Mo. Molecular graphics: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for solid_solution_100K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Cu. Software used to prepare material for publication: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for solid_solution_100K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Cu.
(solid_solution_100K_Cu)
top
Crystal data top
C26H12N4O2 | Z = 2 |
Mr = 412.40 | F(000) = 424 |
Monoclinic, P21/c | Dx = 1.530 Mg m−3 |
a = 11.7955 (11) Å | Cu Kα radiation, λ = 1.54186 Å |
b = 4.7680 (4) Å | µ = 0.82 mm−1 |
c = 16.1261 (14) Å | T = 100 K |
β = 99.354 (7)° | 0.3 × 0.06 × 0.02 mm |
V = 894.89 (14) Å3 | |
Data collection top
8541 measured reflections | θmax = 68.0°, θmin = 3.8° |
1562 independent reflections | h = −13→14 |
953 reflections with I > 2σ(I) | k = −5→5 |
Rint = 0.042 | l = −18→17 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.084 | w = 1/[σ2(Fo2) + (0.1665P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.246 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.52 e Å−3 |
1562 reflections | Δρmin = −0.42 e Å−3 |
205 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
19 restraints | Extinction coefficient: 0.038 (8) |
Primary atom site location: iterative | |
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 | Occ. (<1) |
N001 | 0.7858 (3) | 0.4996 (5) | 0.4361 (2) | 0.0776 (11) | |
C007 | 0.8723 (3) | 0.9877 (6) | 0.6120 (2) | 0.0702 (11) | |
H007 | 0.8149 | 0.9510 | 0.6457 | 0.084* | |
C008 | 0.8673 (4) | 0.5474 (6) | 0.3849 (3) | 0.0763 (12) | |
C009 | 1.0418 (3) | 0.8128 (6) | 0.3617 (2) | 0.0718 (11) | |
H009 | 1.0412 | 0.7161 | 0.3102 | 0.086* | |
C010 | 0.7801 (4) | 0.6364 (7) | 0.5116 (3) | 0.0779 (13) | |
C011 | 0.8712 (3) | 0.8442 (6) | 0.5371 (2) | 0.0658 (10) | |
C012 | 0.9566 (3) | 0.8986 (5) | 0.4865 (2) | 0.0619 (10) | |
C013 | 0.9581 (3) | 0.7556 (6) | 0.4100 (2) | 0.0651 (10) | |
C101 | 0.7097 (3) | 0.2961 (6) | 0.3989 (2) | 0.0655 (10) | |
O101 | 0.6997 (4) | 0.5808 (9) | 0.5572 (3) | 0.0693 (13) | 0.789 (7) |
N101 | 0.8509 (5) | 0.3957 (12) | 0.3204 (4) | 0.0638 (15) | 0.789 (7) |
C100 | 0.7515 (4) | 0.2321 (8) | 0.3267 (3) | 0.0669 (14) | 0.789 (7) |
C102 | 0.6104 (5) | 0.1657 (9) | 0.4208 (4) | 0.0755 (15) | 0.789 (7) |
H102 | 0.5792 | 0.2141 | 0.4696 | 0.091* | 0.789 (7) |
C103 | 0.5628 (7) | −0.0412 (13) | 0.3637 (5) | 0.077 (2) | 0.789 (7) |
H103 | 0.4978 | −0.1417 | 0.3757 | 0.093* | 0.789 (7) |
C104 | 0.6058 (6) | −0.1079 (11) | 0.2900 (5) | 0.091 (2) | 0.789 (7) |
H104 | 0.5694 | −0.2482 | 0.2532 | 0.109* | 0.789 (7) |
C105 | 0.7003 (5) | 0.0297 (9) | 0.2714 (4) | 0.0788 (16) | 0.789 (7) |
H105 | 0.7302 | −0.0128 | 0.2216 | 0.095* | 0.789 (7) |
N201 | 0.7140 (19) | 0.541 (4) | 0.5208 (12) | 0.053 (5) | 0.211 (7) |
O201 | 0.894 (2) | 0.399 (5) | 0.2969 (14) | 0.079 (6) | 0.211 (7) |
C202 | 0.6844 (17) | 0.087 (3) | 0.3328 (16) | 0.079 (5) | 0.211 (7) |
H202 | 0.7357 | 0.0633 | 0.2937 | 0.094* | 0.211 (7) |
C203 | 0.593 (2) | −0.066 (5) | 0.3264 (17) | 0.050 (5)* | 0.211 (7) |
H203 | 0.5716 | −0.1961 | 0.2821 | 0.059* | 0.211 (7) |
C204 | 0.522 (2) | −0.015 (5) | 0.399 (2) | 0.080 (7) | 0.211 (7) |
H204 | 0.4529 | −0.1202 | 0.3977 | 0.096* | 0.211 (7) |
C205 | 0.5528 (16) | 0.181 (4) | 0.4678 (16) | 0.081 (5) | 0.211 (7) |
H205 | 0.5088 | 0.2042 | 0.5116 | 0.097* | 0.211 (7) |
C200 | 0.6530 (13) | 0.331 (3) | 0.4639 (12) | 0.067 (4) | 0.211 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N001 | 0.089 (2) | 0.0434 (14) | 0.086 (2) | −0.0123 (14) | −0.0300 (18) | 0.0132 (14) |
C007 | 0.085 (2) | 0.0453 (16) | 0.072 (2) | 0.0003 (15) | −0.0111 (18) | 0.0071 (15) |
C008 | 0.101 (3) | 0.0365 (15) | 0.075 (3) | 0.0001 (15) | −0.034 (2) | 0.0023 (15) |
C009 | 0.095 (2) | 0.0429 (16) | 0.068 (2) | 0.0023 (15) | −0.0178 (19) | −0.0022 (15) |
C010 | 0.083 (3) | 0.0435 (18) | 0.093 (3) | −0.0037 (17) | −0.029 (2) | 0.0083 (18) |
C011 | 0.078 (2) | 0.0378 (15) | 0.071 (2) | −0.0019 (13) | −0.0191 (18) | 0.0082 (13) |
C012 | 0.076 (2) | 0.0349 (13) | 0.064 (2) | −0.0043 (13) | −0.0207 (17) | 0.0032 (13) |
C013 | 0.083 (2) | 0.0393 (15) | 0.063 (2) | −0.0028 (14) | −0.0189 (17) | 0.0016 (13) |
C101 | 0.074 (2) | 0.0369 (14) | 0.074 (2) | −0.0040 (13) | −0.0216 (17) | 0.0015 (14) |
O101 | 0.075 (3) | 0.059 (2) | 0.072 (3) | −0.0068 (17) | 0.007 (2) | 0.007 (2) |
N101 | 0.083 (4) | 0.0404 (18) | 0.058 (4) | 0.003 (2) | −0.017 (2) | −0.007 (2) |
C100 | 0.083 (3) | 0.036 (2) | 0.068 (3) | 0.005 (2) | −0.028 (2) | −0.0031 (17) |
C102 | 0.080 (3) | 0.048 (2) | 0.087 (4) | −0.008 (2) | −0.024 (3) | 0.003 (2) |
C103 | 0.068 (5) | 0.049 (3) | 0.102 (7) | −0.008 (3) | −0.025 (4) | −0.001 (4) |
C104 | 0.106 (4) | 0.051 (2) | 0.097 (5) | 0.000 (3) | −0.037 (4) | −0.015 (3) |
C105 | 0.089 (3) | 0.046 (2) | 0.085 (4) | 0.008 (2) | −0.036 (3) | −0.009 (2) |
N201 | 0.057 (9) | 0.055 (9) | 0.053 (12) | 0.020 (7) | 0.030 (10) | 0.014 (8) |
O201 | 0.097 (15) | 0.067 (8) | 0.071 (12) | −0.001 (9) | 0.009 (9) | −0.021 (7) |
C202 | 0.080 (11) | 0.036 (7) | 0.107 (14) | −0.018 (8) | −0.024 (10) | −0.016 (8) |
C204 | 0.073 (16) | 0.036 (9) | 0.11 (2) | −0.013 (10) | −0.033 (12) | 0.027 (9) |
C205 | 0.058 (9) | 0.073 (11) | 0.100 (15) | −0.007 (8) | −0.019 (8) | 0.018 (9) |
C200 | 0.058 (8) | 0.048 (8) | 0.087 (10) | −0.003 (6) | −0.017 (7) | 0.001 (7) |
Geometric parameters (Å, º) top
N001—C008 | 1.383 (5) | C101—C202 | 1.45 (2) |
N001—C010 | 1.392 (6) | C101—C200 | 1.34 (2) |
N001—C101 | 1.390 (4) | N101—C100 | 1.425 (8) |
N001—C200 | 1.879 (17) | C100—C105 | 1.384 (6) |
C007—H007 | 0.9500 | C102—H102 | 0.9500 |
C007—C009i | 1.404 (5) | C102—C103 | 1.402 (7) |
C007—C011 | 1.388 (5) | C103—H103 | 0.9500 |
C008—C013 | 1.468 (5) | C103—C104 | 1.402 (10) |
C008—N101 | 1.256 (7) | C104—H104 | 0.9500 |
C008—O201 | 1.66 (2) | C104—C105 | 1.369 (9) |
C009—C007i | 1.404 (5) | C105—H105 | 0.9500 |
C009—H009 | 0.9500 | N201—C200 | 1.47 (3) |
C009—C013 | 1.380 (5) | C202—H202 | 0.9500 |
C010—C011 | 1.471 (5) | C202—C203 | 1.29 (3) |
C010—O101 | 1.318 (7) | C203—H203 | 0.9500 |
C010—N201 | 0.93 (2) | C203—C204 | 1.57 (3) |
C011—C012 | 1.419 (5) | C204—H204 | 0.9500 |
C012—C012i | 1.424 (6) | C204—C205 | 1.45 (3) |
C012—C013 | 1.412 (5) | C205—H205 | 0.9500 |
C101—C100 | 1.370 (6) | C205—C200 | 1.39 (2) |
C101—C102 | 1.421 (7) | | |
| | | |
C008—N001—C010 | 125.6 (3) | C200—C101—C202 | 126.0 (12) |
C008—N001—C101 | 108.6 (3) | C008—N101—C100 | 105.9 (5) |
C008—N001—C200 | 154.1 (6) | C101—C100—N101 | 110.6 (4) |
C010—N001—C200 | 80.2 (6) | C101—C100—C105 | 121.5 (5) |
C101—N001—C010 | 125.8 (4) | C105—C100—N101 | 127.9 (5) |
C101—N001—C200 | 45.5 (6) | C101—C102—H102 | 123.1 |
C009i—C007—H007 | 120.0 | C103—C102—C101 | 113.8 (6) |
C011—C007—H007 | 120.0 | C103—C102—H102 | 123.1 |
C011—C007—C009i | 120.0 (4) | C102—C103—H103 | 118.2 |
N001—C008—C013 | 119.5 (3) | C104—C103—C102 | 123.6 (7) |
N001—C008—O201 | 133.5 (9) | C104—C103—H103 | 118.2 |
C013—C008—O201 | 106.8 (9) | C103—C104—H104 | 120.1 |
N101—C008—N001 | 111.8 (4) | C105—C104—C103 | 119.8 (6) |
N101—C008—C013 | 128.6 (5) | C105—C104—H104 | 120.1 |
C007i—C009—H009 | 119.6 | C100—C105—H105 | 120.7 |
C013—C009—C007i | 120.8 (3) | C104—C105—C100 | 118.6 (6) |
C013—C009—H009 | 119.6 | C104—C105—H105 | 120.7 |
N001—C010—C011 | 115.0 (4) | C010—N201—C200 | 124.7 (17) |
O101—C010—N001 | 122.4 (4) | C101—C202—H202 | 119.5 |
O101—C010—C011 | 122.6 (4) | C203—C202—C101 | 121 (2) |
N201—C010—N001 | 94.1 (13) | C203—C202—H202 | 119.5 |
N201—C010—C011 | 150.9 (14) | C202—C203—H203 | 123.3 |
C007—C011—C010 | 118.6 (4) | C202—C203—C204 | 113 (2) |
C007—C011—C012 | 120.2 (3) | C204—C203—H203 | 123.3 |
C012—C011—C010 | 121.2 (4) | C203—C204—H204 | 117.7 |
C011—C012—C012i | 119.4 (4) | C205—C204—C203 | 125 (2) |
C013—C012—C011 | 121.6 (3) | C205—C204—H204 | 117.7 |
C013—C012—C012i | 119.0 (4) | C204—C205—H205 | 122.9 |
C009—C013—C008 | 122.3 (3) | C200—C205—C204 | 114 (2) |
C009—C013—C012 | 120.6 (3) | C200—C205—H205 | 122.9 |
C012—C013—C008 | 117.1 (4) | C101—C200—N001 | 47.6 (6) |
N001—C101—C102 | 134.3 (4) | C101—C200—N201 | 108.5 (13) |
N001—C101—C202 | 146.8 (10) | C101—C200—C205 | 120.4 (17) |
C100—C101—N001 | 103.1 (4) | N201—C200—N001 | 60.9 (9) |
C100—C101—C102 | 122.6 (4) | C205—C200—N001 | 167.9 (18) |
C200—C101—N001 | 86.8 (7) | C205—C200—N201 | 131 (2) |
| | | |
N001—C008—C013—C009 | 180.0 (3) | C101—N001—C010—O101 | 1.0 (6) |
N001—C008—C013—C012 | −0.2 (4) | C101—N001—C010—N201 | −0.1 (12) |
N001—C008—N101—C100 | 0.2 (5) | C101—N001—C200—N201 | 178.8 (12) |
N001—C010—C011—C007 | −179.3 (3) | C101—N001—C200—C205 | −7 (6) |
N001—C010—C011—C012 | 0.7 (4) | C101—C100—C105—C104 | 0.0 (6) |
N001—C010—N201—C200 | −0.9 (19) | C101—C102—C103—C104 | −2.3 (9) |
N001—C101—C100—N101 | −0.3 (4) | C101—C202—C203—C204 | −4 (4) |
N001—C101—C100—C105 | 178.7 (3) | O101—C010—C011—C007 | −0.2 (5) |
N001—C101—C102—C103 | −177.7 (4) | O101—C010—C011—C012 | 179.9 (3) |
N001—C101—C202—C203 | 178.3 (16) | O101—C010—N201—C200 | −179 (4) |
N001—C101—C200—N201 | −1.1 (11) | N101—C008—C013—C009 | 0.2 (6) |
N001—C101—C200—C205 | 178.3 (14) | N101—C008—C013—C012 | −180.0 (4) |
C007i—C009—C013—C008 | −179.6 (3) | N101—C100—C105—C104 | 178.8 (5) |
C007i—C009—C013—C012 | 0.5 (5) | C100—C101—C102—C103 | 2.5 (6) |
C007—C011—C012—C012i | 0.1 (5) | C100—C101—C202—C203 | −168 (3) |
C007—C011—C012—C013 | 179.8 (3) | C100—C101—C200—N001 | −171 (4) |
C008—N001—C010—C011 | −1.0 (5) | C100—C101—C200—N201 | −172 (3) |
C008—N001—C010—O101 | 179.8 (4) | C100—C101—C200—C205 | 7 (5) |
C008—N001—C010—N201 | 178.7 (12) | C102—C101—C100—N101 | 179.5 (4) |
C008—N001—C101—C100 | 0.5 (3) | C102—C101—C100—C105 | −1.5 (5) |
C008—N001—C101—C102 | −179.3 (4) | C102—C101—C202—C203 | 5 (2) |
C008—N001—C101—C202 | 10.1 (14) | C102—C101—C200—N001 | 178.7 (7) |
C008—N001—C101—C200 | −178.0 (7) | C102—C101—C200—N201 | 177.6 (16) |
C008—N001—C200—C101 | 4.3 (14) | C102—C101—C200—C205 | −3.0 (10) |
C008—N001—C200—N201 | −176.9 (11) | C102—C103—C104—C105 | 1.0 (10) |
C008—N001—C200—C205 | −3 (7) | C103—C104—C105—C100 | 0.3 (8) |
C008—N101—C100—C101 | 0.1 (5) | N201—C010—C011—C007 | 1 (3) |
C008—N101—C100—C105 | −178.8 (4) | N201—C010—C011—C012 | −179 (2) |
C009i—C007—C011—C010 | 179.9 (3) | O201—C008—C013—C009 | 3.7 (9) |
C009i—C007—C011—C012 | −0.1 (5) | O201—C008—C013—C012 | −176.5 (9) |
C010—N001—C008—C013 | 0.8 (5) | O201—C008—N101—C100 | 171 (3) |
C010—N001—C008—N101 | −179.4 (4) | C202—C101—C100—N101 | −172.8 (11) |
C010—N001—C008—O201 | 175.9 (12) | C202—C101—C100—C105 | 6.2 (11) |
C010—N001—C101—C100 | 179.4 (3) | C202—C101—C102—C103 | −3.0 (9) |
C010—N001—C101—C102 | −0.4 (6) | C202—C101—C200—N001 | 174.5 (10) |
C010—N001—C101—C202 | −171.0 (14) | C202—C101—C200—N201 | 173.4 (12) |
C010—N001—C101—C200 | 0.9 (7) | C202—C101—C200—C205 | −7.2 (19) |
C010—N001—C200—C101 | −179.2 (6) | C202—C203—C204—C205 | −1 (4) |
C010—N001—C200—N201 | −0.4 (9) | C203—C204—C205—C200 | 2 (4) |
C010—N001—C200—C205 | 174 (6) | C204—C205—C200—N001 | 8 (7) |
C010—C011—C012—C012i | −180.0 (3) | C204—C205—C200—C101 | 2 (2) |
C010—C011—C012—C013 | −0.2 (4) | C204—C205—C200—N201 | −178.6 (19) |
C010—N201—C200—N001 | 0.8 (16) | C200—N001—C008—C013 | 176.5 (11) |
C010—N201—C200—C101 | 2 (2) | C200—N001—C008—N101 | −3.7 (12) |
C010—N201—C200—C205 | −177.5 (18) | C200—N001—C008—O201 | −8.4 (17) |
C011—C010—N201—C200 | 178.6 (9) | C200—N001—C010—C011 | −179.1 (5) |
C011—C012—C013—C008 | −0.1 (4) | C200—N001—C010—O101 | 1.7 (6) |
C011—C012—C013—C009 | 179.8 (3) | C200—N001—C010—N201 | 0.6 (13) |
C012i—C012—C013—C008 | 179.7 (3) | C200—N001—C101—C100 | 178.5 (7) |
C012i—C012—C013—C009 | −0.5 (5) | C200—N001—C101—C102 | −1.3 (7) |
C013—C008—N101—C100 | 180.0 (3) | C200—N001—C101—C202 | −171.9 (16) |
C101—N001—C008—C013 | 179.7 (3) | C200—C101—C100—N101 | 171 (4) |
C101—N001—C008—N101 | −0.4 (5) | C200—C101—C100—C105 | −10 (4) |
C101—N001—C008—O201 | −5.2 (12) | C200—C101—C102—C103 | −179.5 (10) |
C101—N001—C010—C011 | −179.8 (3) | C200—C101—C202—C203 | 8 (3) |
Symmetry code: (i) −x+2, −y+2, −z+1. |
(solid_solution_293K_Cu)
top
Crystal data top
C26H12N4O2 | F(000) = 424 |
Mr = 412.40 | Dx = 1.505 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 11.808 (3) Å | Cell parameters from 3946 reflections |
b = 4.8032 (10) Å | θ = 5.5–49.5° |
c = 16.246 (4) Å | µ = 0.80 mm−1 |
β = 99.002 (9)° | T = 293 K |
V = 910.1 (4) Å3 | Plate, brown |
Z = 2 | 0.30 × 0.13 × 0.02 mm |
Data collection top
Bruker AXS three circle goniometer diffractometer | 1677 independent reflections |
Radiation source: Incoatec IµS microfocus X-ray source, micro focus source | 1225 reflections with I > 2σ(I) |
Incoatec Quazar Multilayer Mirror monochromator | Rint = 0.037 |
Detector resolution: 8.33 pixels mm-1 | θmax = 69.6°, θmin = 3.8° |
ω scan | h = −14→13 |
Absorption correction: empirical (using intensity measurements) (G. M. Sheldrick. SADABS), 2008.) | k = −5→5 |
Tmin = 0.614, Tmax = 0.753 | l = −19→19 |
9979 measured reflections | |
Refinement top
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.4338P] where P = (Fo2 + 2Fc2)/3 |
1677 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.16 e Å−3 |
24 restraints | Δρmin = −0.11 e Å−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 | Occ. (<1) |
N001 | 0.71361 (19) | 0.5051 (4) | 0.06401 (14) | 0.0801 (7) | |
C001 | 0.6262 (2) | 0.9812 (5) | −0.11143 (15) | 0.0766 (7) | |
H001 | 0.6822 | 0.9438 | −0.1442 | 0.092* | |
C002 | 0.4591 (2) | 0.8221 (5) | 0.13789 (15) | 0.0776 (7) | |
H002 | 0.4600 | 0.7314 | 0.1886 | 0.093* | |
C003 | 0.5420 (2) | 0.7614 (4) | 0.08927 (14) | 0.0659 (6) | |
C004 | 0.54320 (19) | 0.8999 (4) | 0.01330 (13) | 0.0619 (6) | |
C005 | 0.6277 (2) | 0.8431 (4) | −0.03718 (14) | 0.0666 (6) | |
C006 | 0.7195 (3) | 0.6362 (5) | −0.01176 (19) | 0.0813 (8) | |
C007 | 0.6326 (2) | 0.5548 (4) | 0.11513 (16) | 0.0756 (7) | |
C200 | 0.7896 (2) | 0.3042 (4) | 0.10100 (17) | 0.0693 (7) | |
N101 | 0.7884 (16) | 0.541 (4) | −0.0208 (10) | 0.063 (4) | 0.200 (6) |
O101 | 0.6038 (14) | 0.417 (4) | 0.2020 (9) | 0.094 (5) | 0.200 (6) |
C101 | 0.8404 (11) | 0.338 (3) | 0.0372 (9) | 0.078 (4) | 0.200 (6) |
C102 | 0.9404 (15) | 0.181 (4) | 0.0322 (13) | 0.106 (5) | 0.200 (6) |
H102 | 0.9836 | 0.2016 | −0.0106 | 0.127* | 0.200 (6) |
C103 | 0.968 (3) | −0.007 (9) | 0.097 (2) | 0.123 (8) | 0.200 (6) |
H103 | 1.0281 | −0.1287 | 0.0934 | 0.148* | 0.200 (6) |
C104 | 0.911 (3) | −0.032 (8) | 0.173 (3) | 0.114 (10) | 0.200 (6) |
H104 | 0.9409 | −0.1371 | 0.2192 | 0.137* | 0.200 (6) |
C105 | 0.8117 (13) | 0.111 (3) | 0.1683 (12) | 0.083 (4) | 0.200 (6) |
H105 | 0.7613 | 0.0855 | 0.2064 | 0.099* | 0.200 (6) |
N201 | 0.6488 (4) | 0.4076 (8) | 0.1792 (3) | 0.0699 (10) | 0.800 (6) |
O201 | 0.7984 (4) | 0.5783 (10) | −0.0572 (2) | 0.0878 (12) | 0.800 (6) |
C201 | 0.7477 (3) | 0.2458 (6) | 0.1729 (2) | 0.0743 (11) | 0.800 (6) |
C202 | 0.8001 (3) | 0.0458 (7) | 0.2286 (3) | 0.0929 (13) | 0.800 (6) |
H202 | 0.7729 | 0.0069 | 0.2781 | 0.111* | 0.800 (6) |
C203 | 0.8944 (6) | −0.0923 (13) | 0.2072 (4) | 0.108 (2) | 0.800 (6) |
H203 | 0.9290 | −0.2333 | 0.2415 | 0.129* | 0.800 (6) |
C204 | 0.9373 (7) | −0.0248 (18) | 0.1366 (4) | 0.101 (2) | 0.800 (6) |
H204 | 1.0026 | −0.1170 | 0.1256 | 0.121* | 0.800 (6) |
C205 | 0.8883 (4) | 0.1750 (8) | 0.0802 (3) | 0.0882 (12) | 0.800 (6) |
H205 | 0.9185 | 0.2201 | 0.0324 | 0.106* | 0.800 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N001 | 0.0893 (15) | 0.0481 (11) | 0.0891 (15) | 0.0095 (10) | −0.0295 (12) | −0.0151 (11) |
C001 | 0.0901 (17) | 0.0603 (14) | 0.0745 (16) | −0.0016 (13) | −0.0021 (13) | −0.0065 (12) |
C002 | 0.1032 (18) | 0.0560 (14) | 0.0650 (14) | −0.0053 (13) | −0.0140 (13) | 0.0030 (11) |
C003 | 0.0831 (15) | 0.0441 (11) | 0.0615 (13) | −0.0027 (11) | −0.0162 (11) | −0.0044 (10) |
C004 | 0.0774 (14) | 0.0386 (10) | 0.0597 (13) | −0.0043 (10) | −0.0203 (11) | −0.0062 (9) |
C005 | 0.0775 (15) | 0.0455 (12) | 0.0685 (14) | 0.0002 (10) | −0.0143 (12) | −0.0116 (10) |
C006 | 0.092 (2) | 0.0502 (14) | 0.088 (2) | 0.0008 (14) | −0.0277 (16) | −0.0121 (13) |
C007 | 0.0964 (18) | 0.0426 (12) | 0.0735 (16) | −0.0035 (12) | −0.0312 (14) | −0.0018 (11) |
C200 | 0.0779 (15) | 0.0411 (11) | 0.0775 (16) | 0.0017 (11) | −0.0238 (13) | −0.0034 (11) |
N101 | 0.055 (6) | 0.070 (9) | 0.069 (10) | 0.004 (6) | 0.029 (8) | −0.024 (8) |
O101 | 0.112 (11) | 0.100 (8) | 0.076 (8) | 0.027 (8) | 0.029 (6) | 0.042 (6) |
C101 | 0.066 (7) | 0.076 (9) | 0.080 (8) | 0.003 (6) | −0.023 (5) | −0.015 (7) |
C102 | 0.097 (11) | 0.093 (11) | 0.119 (13) | 0.035 (9) | −0.010 (8) | −0.027 (10) |
C103 | 0.123 (18) | 0.097 (14) | 0.13 (2) | 0.025 (14) | −0.026 (12) | −0.016 (15) |
C104 | 0.096 (15) | 0.051 (13) | 0.19 (3) | 0.022 (11) | −0.001 (18) | 0.04 (2) |
C105 | 0.078 (8) | 0.043 (7) | 0.108 (10) | −0.003 (6) | −0.045 (7) | 0.023 (7) |
N201 | 0.090 (3) | 0.0495 (15) | 0.062 (2) | −0.0071 (19) | −0.0145 (17) | 0.0082 (15) |
O201 | 0.094 (2) | 0.090 (2) | 0.080 (3) | 0.0190 (16) | 0.0145 (19) | −0.006 (2) |
C201 | 0.086 (2) | 0.0420 (17) | 0.080 (2) | −0.0069 (17) | −0.0324 (17) | 0.0043 (15) |
C202 | 0.103 (3) | 0.055 (2) | 0.103 (3) | −0.0087 (18) | −0.040 (2) | 0.0186 (19) |
C203 | 0.107 (4) | 0.052 (3) | 0.139 (4) | −0.001 (3) | −0.059 (3) | 0.016 (3) |
C204 | 0.096 (6) | 0.061 (3) | 0.125 (7) | 0.015 (4) | −0.051 (4) | −0.008 (5) |
C205 | 0.091 (3) | 0.065 (2) | 0.097 (3) | 0.012 (2) | −0.022 (2) | −0.012 (2) |
Geometric parameters (Å, º) top
N001—C007 | 1.383 (3) | C200—C205 | 1.408 (5) |
N001—C200 | 1.388 (3) | C200—C105 | 1.427 (15) |
N001—C006 | 1.394 (4) | N101—C101 | 1.43 (3) |
C001—C005 | 1.374 (3) | C101—C102 | 1.41 (2) |
C001—C002i | 1.399 (3) | C102—C103 | 1.39 (4) |
C001—H001 | 0.9300 | C102—H102 | 0.9300 |
C002—C003 | 1.382 (3) | C103—C104 | 1.50 (4) |
C002—C001i | 1.399 (3) | C103—H103 | 0.9300 |
C002—H002 | 0.9300 | C104—C105 | 1.35 (4) |
C003—C004 | 1.404 (3) | C104—H104 | 0.9300 |
C003—C007 | 1.471 (3) | C105—H105 | 0.9300 |
C004—C005 | 1.414 (3) | N201—C201 | 1.420 (6) |
C004—C004i | 1.419 (4) | C201—C202 | 1.397 (5) |
C005—C006 | 1.481 (3) | C202—C203 | 1.387 (7) |
C006—N101 | 0.963 (18) | C202—H202 | 0.9300 |
C006—O201 | 1.306 (5) | C203—C204 | 1.363 (8) |
C007—N201 | 1.248 (5) | C203—H203 | 0.9300 |
C007—O101 | 1.641 (14) | C204—C205 | 1.389 (7) |
C200—C101 | 1.286 (15) | C204—H204 | 0.9300 |
C200—C201 | 1.367 (4) | C205—H205 | 0.9300 |
| | | |
C007—N001—C200 | 108.7 (2) | N001—C200—C105 | 144.3 (9) |
C007—N001—C006 | 126.0 (2) | C006—N101—C101 | 120.6 (15) |
C200—N001—C006 | 125.3 (3) | C200—C101—C102 | 118.6 (15) |
C005—C001—C002i | 120.4 (3) | C200—C101—N101 | 114.3 (12) |
C005—C001—H001 | 119.8 | C102—C101—N101 | 127.1 (16) |
C002i—C001—H001 | 119.8 | C103—C102—C101 | 114 (2) |
C003—C002—C001i | 120.5 (2) | C103—C102—H102 | 123.1 |
C003—C002—H002 | 119.8 | C101—C102—H102 | 123.1 |
C001i—C002—H002 | 119.8 | C102—C103—C104 | 126 (3) |
C002—C003—C004 | 120.5 (2) | C102—C103—H103 | 116.8 |
C002—C003—C007 | 121.8 (2) | C104—C103—H103 | 116.8 |
C004—C003—C007 | 117.6 (2) | C105—C104—C103 | 114 (3) |
C003—C004—C005 | 121.6 (2) | C105—C104—H104 | 122.8 |
C003—C004—C004i | 118.9 (3) | C103—C104—H104 | 122.8 |
C005—C004—C004i | 119.5 (3) | C104—C105—C200 | 115 (2) |
C001—C005—C004 | 120.2 (2) | C104—C105—H105 | 122.4 |
C001—C005—C006 | 118.5 (3) | C200—C105—H105 | 122.4 |
C004—C005—C006 | 121.3 (2) | C007—N201—C201 | 105.7 (4) |
N101—C006—N001 | 94.6 (11) | C200—C201—C202 | 120.8 (4) |
O201—C006—N001 | 122.8 (3) | C200—C201—N201 | 111.2 (3) |
N101—C006—C005 | 150.9 (11) | C202—C201—N201 | 128.0 (4) |
O201—C006—C005 | 122.8 (3) | C203—C202—C201 | 117.2 (4) |
N001—C006—C005 | 114.4 (3) | C203—C202—H202 | 121.4 |
N201—C007—N001 | 111.9 (3) | C201—C202—H202 | 121.4 |
N201—C007—C003 | 129.1 (3) | C204—C203—C202 | 121.1 (5) |
N001—C007—C003 | 119.0 (2) | C204—C203—H203 | 119.4 |
N001—C007—O101 | 134.7 (6) | C202—C203—H203 | 119.4 |
C003—C007—O101 | 106.1 (6) | C203—C204—C205 | 123.2 (7) |
C101—C200—N001 | 85.1 (6) | C203—C204—H204 | 118.4 |
C201—C200—N001 | 102.5 (3) | C205—C204—H204 | 118.4 |
C201—C200—C205 | 122.6 (3) | C204—C205—C200 | 115.0 (5) |
N001—C200—C205 | 134.9 (3) | C204—C205—H205 | 122.5 |
C101—C200—C105 | 130.3 (10) | C200—C205—H205 | 122.5 |
| | | |
C001i—C002—C003—C004 | 1.2 (3) | C007—N001—C200—C105 | 7.6 (9) |
C001i—C002—C003—C007 | −179.72 (19) | C006—N001—C200—C105 | −173.1 (9) |
C002—C003—C004—C005 | 179.48 (19) | O201—C006—N101—C101 | −174 (4) |
C007—C003—C004—C005 | 0.3 (3) | N001—C006—N101—C101 | 1.8 (17) |
C002—C003—C004—C004i | −0.9 (3) | C005—C006—N101—C101 | 178.9 (8) |
C007—C003—C004—C004i | 179.9 (2) | N001—C200—C101—C102 | 179.1 (12) |
C002i—C001—C005—C004 | −0.3 (3) | C205—C200—C101—C102 | −0.7 (10) |
C002i—C001—C005—C006 | 179.90 (19) | C105—C200—C101—C102 | −5.9 (16) |
C003—C004—C005—C001 | 179.70 (19) | N001—C200—C101—N101 | 0.6 (11) |
C004i—C004—C005—C001 | 0.1 (3) | C205—C200—C101—N101 | −179.2 (14) |
C003—C004—C005—C006 | −0.6 (3) | C105—C200—C101—N101 | 175.6 (11) |
C004i—C004—C005—C006 | 179.9 (2) | C006—N101—C101—C200 | −2 (2) |
C007—N001—C006—N101 | 177.7 (11) | C006—N101—C101—C102 | 179.6 (16) |
C200—N001—C006—N101 | −1.5 (11) | C200—C101—C102—C103 | 3 (3) |
C007—N001—C006—O201 | −179.7 (3) | N101—C101—C102—C103 | −178 (3) |
C200—N001—C006—O201 | 1.1 (4) | C101—C102—C103—C104 | −7 (6) |
C007—N001—C006—C005 | −0.8 (3) | C102—C103—C104—C105 | 12 (8) |
C200—N001—C006—C005 | 180.00 (18) | C103—C104—C105—C200 | −12 (5) |
C001—C005—C006—N101 | 4 (2) | C101—C200—C105—C104 | 11 (3) |
C004—C005—C006—N101 | −176 (2) | C201—C200—C105—C104 | −167 (3) |
C001—C005—C006—O201 | −0.6 (4) | N001—C200—C105—C104 | −178 (2) |
C004—C005—C006—O201 | 179.6 (3) | C205—C200—C105—C104 | 7 (2) |
C001—C005—C006—N001 | −179.52 (19) | N001—C007—N201—C201 | 0.3 (3) |
C004—C005—C006—N001 | 0.7 (3) | C003—C007—N201—C201 | 179.9 (2) |
C200—N001—C007—N201 | −0.4 (3) | O101—C007—N201—C201 | 172 (2) |
C006—N001—C007—N201 | −179.7 (2) | N001—C200—C201—C202 | 179.0 (2) |
C200—N001—C007—C003 | 179.95 (17) | C205—C200—C201—C202 | −1.9 (4) |
C006—N001—C007—C003 | 0.6 (3) | C105—C200—C201—C202 | 5.4 (7) |
C200—N001—C007—O101 | −5.1 (9) | N001—C200—C201—N201 | −0.1 (3) |
C006—N001—C007—O101 | 175.6 (9) | C205—C200—C201—N201 | 179.0 (3) |
C002—C003—C007—N201 | 0.9 (4) | C105—C200—C201—N201 | −173.7 (8) |
C004—C003—C007—N201 | −180.0 (3) | C007—N201—C201—C200 | −0.2 (3) |
C002—C003—C007—N001 | −179.5 (2) | C007—N201—C201—C202 | −179.2 (3) |
C004—C003—C007—N001 | −0.4 (3) | C200—C201—C202—C203 | −1.0 (5) |
C002—C003—C007—O101 | 4.3 (7) | N201—C201—C202—C203 | 177.9 (4) |
C004—C003—C007—O101 | −176.6 (7) | C201—C202—C203—C204 | 3.2 (9) |
C007—N001—C200—C101 | −178.9 (5) | C202—C203—C204—C205 | −2.6 (13) |
C006—N001—C200—C101 | 0.4 (6) | C203—C204—C205—C200 | −0.3 (11) |
C007—N001—C200—C201 | 0.2 (2) | C101—C200—C205—C204 | −178.4 (9) |
C006—N001—C200—C201 | 179.6 (2) | C201—C200—C205—C204 | 2.5 (6) |
C007—N001—C200—C205 | −178.7 (3) | N001—C200—C205—C204 | −178.7 (5) |
C006—N001—C200—C205 | 0.7 (4) | C105—C200—C205—C204 | −2.4 (7) |
Symmetry code: (i) −x+1, −y+2, −z. |
(solid_solution_293K_Mo)
top
Crystal data top
C26H12N4O2 | F(000) = 424 |
Mr = 412.40 | Dx = 1.506 Mg m−3 Dm = 1.549 Mg m−3 Dm measured by not measured |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 947 reflections |
a = 11.7980 (16) Å | θ = 1.8–20.8° |
b = 4.8049 (6) Å | µ = 0.10 mm−1 |
c = 16.239 (2) Å | T = 293 K |
β = 99.021 (2)° | Plate, brown |
V = 909.2 (2) Å3 | 0.3 × 0.06 × 0.02 mm |
Z = 2 | |
Data collection top
Three-circle diffractometer with SIEMENS CCD detector | 519 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
Graphite monochromator | θmax = 20.8°, θmin = 1.8° |
ω– and phi–scans, step width 0.3 deg. | h = −11→11 |
3103 measured reflections | k = −4→4 |
947 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.3463P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
947 reflections | Δρmax = 0.15 e Å−3 |
175 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (4) |
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. |
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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C01 | 0.3745 (7) | 0.3447 (12) | 0.5360 (5) | 0.072 (2) | |
C02 | 0.3742 (7) | 0.4798 (14) | 0.6108 (5) | 0.083 (2) | |
C03 | 0.4577 (5) | 0.3976 (11) | 0.4863 (5) | 0.0629 (19) | |
C04 | 0.4581 (7) | 0.2611 (13) | 0.4100 (5) | 0.072 (2) | |
C05 | 0.5392 (7) | 0.3182 (14) | 0.3623 (5) | 0.082 (2) | |
C06 | 0.2827 (8) | 0.1381 (16) | 0.5105 (6) | 0.092 (3) | |
C07 | 0.3672 (7) | 0.0533 (13) | 0.3844 (6) | 0.080 (2) | |
H02 | 0.310 (4) | 0.440 (10) | 0.647 (3) | 0.07 (2)* | |
H05 | 0.549 (4) | 0.245 (11) | 0.305 (3) | 0.08 (2)* | |
N1 | 0.2862 (6) | 0.0035 (11) | 0.4353 (5) | 0.085 (2) | |
N2 | 0.3602 (6) | −0.0900 (12) | 0.3169 (4) | 0.099 (2) | |
O1 | 0.2048 (5) | 0.0747 (11) | 0.5519 (4) | 0.118 (2) | |
C08 | 0.1954 (16) | −0.194 (3) | 0.4118 (12) | 0.041 (5)* | 0.54 (2) |
C09 | 0.2424 (17) | −0.263 (3) | 0.3320 (14) | 0.047 (5)* | 0.54 (2) |
C10 | 0.1882 (15) | −0.450 (3) | 0.2842 (13) | 0.067 (5)* | 0.54 (2) |
H10 | 0.2153 | −0.4894 | 0.2347 | 0.100* | 0.54 (2) |
C11 | 0.0968 (15) | −0.592 (3) | 0.2997 (17) | 0.060 (5)* | 0.54 (2) |
H11 | 0.0623 | −0.7271 | 0.2631 | 0.090* | 0.54 (2) |
C12 | 0.056 (3) | −0.529 (4) | 0.3726 (17) | 0.068 (7)* | 0.54 (2) |
H12 | −0.0064 | −0.6323 | 0.3849 | 0.102* | 0.54 (2) |
C13 | 0.101 (2) | −0.317 (6) | 0.431 (2) | 0.103 (11)* | 0.54 (2) |
H13 | 0.0682 | −0.2693 | 0.4772 | 0.155* | 0.54 (2) |
C081 | 0.236 (2) | −0.211 (6) | 0.388 (2) | 0.026 (9)* | 0.29 (2) |
C091 | 0.281 (3) | −0.231 (6) | 0.3102 (18) | 0.049 (9)* | 0.29 (2) |
C101 | 0.224 (2) | −0.438 (4) | 0.2538 (16) | 0.051 (8)* | 0.29 (2) |
H101 | 0.2527 | −0.4801 | 0.2051 | 0.077* | 0.29 (2) |
C111 | 0.131 (3) | −0.571 (6) | 0.2713 (19) | 0.064 (9)* | 0.29 (2) |
H111 | 0.0921 | −0.6885 | 0.2307 | 0.096* | 0.29 (2) |
C121 | 0.091 (3) | −0.548 (6) | 0.340 (3) | 0.040 (9)* | 0.29 (2) |
H121 | 0.0340 | −0.6752 | 0.3476 | 0.060* | 0.29 (2) |
C131 | 0.123 (3) | −0.339 (6) | 0.410 (2) | 0.041 (9)* | 0.29 (2) |
H131 | 0.0852 | −0.2977 | 0.4550 | 0.062* | 0.29 (2) |
C082 | 0.208 (5) | −0.179 (10) | 0.380 (4) | 0.029 (16)* | 0.17 (14) |
C092 | 0.163 (4) | −0.153 (8) | 0.471 (3) | 0.073 (15)* | 0.17 (14) |
C102 | 0.054 (4) | −0.306 (8) | 0.470 (3) | 0.079 (14)* | 0.17 (14) |
H102 | 0.0109 | −0.2747 | 0.5125 | 0.119* | 0.17 (14) |
C112 | 0.017 (3) | −0.491 (7) | 0.409 (2) | 0.045 (11)* | 0.17 (14) |
H112 | −0.0395 | −0.6189 | 0.4175 | 0.068* | 0.17 (14) |
C122 | 0.054 (7) | −0.495 (14) | 0.347 (6) | 0.08 (3)* | 0.17 (14) |
H122 | 0.0154 | −0.5745 | 0.2986 | 0.124* | 0.17 (14) |
C132 | 0.170 (4) | −0.358 (8) | 0.353 (3) | 0.057 (13)* | 0.17 (14) |
H132 | 0.2202 | −0.4602 | 0.3262 | 0.086* | 0.17 (14) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C01 | 0.097 (6) | 0.040 (4) | 0.068 (5) | −0.003 (4) | −0.018 (5) | 0.002 (4) |
C02 | 0.100 (6) | 0.058 (5) | 0.087 (6) | 0.000 (5) | 0.003 (5) | 0.011 (5) |
C03 | 0.080 (6) | 0.044 (4) | 0.059 (5) | 0.001 (3) | −0.007 (4) | 0.011 (4) |
C04 | 0.102 (6) | 0.047 (4) | 0.060 (6) | 0.012 (5) | −0.012 (4) | 0.003 (4) |
C05 | 0.114 (7) | 0.060 (5) | 0.065 (6) | 0.004 (5) | −0.007 (5) | −0.001 (4) |
C06 | 0.108 (7) | 0.060 (6) | 0.098 (8) | 0.009 (6) | −0.016 (6) | 0.018 (5) |
C07 | 0.103 (6) | 0.041 (5) | 0.081 (6) | −0.002 (4) | −0.036 (6) | 0.005 (5) |
N1 | 0.104 (5) | 0.051 (4) | 0.085 (5) | −0.003 (4) | −0.026 (5) | 0.016 (4) |
N2 | 0.138 (6) | 0.050 (3) | 0.088 (5) | 0.007 (4) | −0.048 (4) | −0.023 (3) |
O1 | 0.122 (5) | 0.092 (4) | 0.134 (5) | −0.013 (4) | −0.007 (4) | 0.017 (4) |
Geometric parameters (Å, º) top
C01—C02 | 1.378 (8) | C10—H10 | 0.9300 |
C01—C03 | 1.388 (8) | C11—C12 | 1.38 (3) |
C01—C06 | 1.480 (9) | C11—H11 | 0.9300 |
C02—C05i | 1.426 (9) | C12—C13 | 1.44 (3) |
C02—H02 | 1.05 (5) | C12—H12 | 0.9300 |
C03—C04 | 1.403 (8) | C13—H13 | 0.9300 |
C03—C03i | 1.422 (11) | C081—C091 | 1.45 (5) |
C04—C05 | 1.351 (8) | C081—C131 | 1.56 (5) |
C04—C07 | 1.476 (8) | C091—C101 | 1.44 (3) |
C05—C02i | 1.426 (9) | C101—C111 | 1.34 (4) |
C05—H05 | 1.02 (5) | C101—H101 | 0.9300 |
C06—O1 | 1.258 (8) | C111—C121 | 1.28 (6) |
C06—N1 | 1.389 (9) | C111—H111 | 0.9300 |
C07—N2 | 1.285 (8) | C121—C131 | 1.53 (6) |
C07—N1 | 1.378 (8) | C121—H121 | 0.9300 |
N1—C081 | 1.36 (3) | C131—H131 | 0.9300 |
N1—C08 | 1.438 (17) | C082—C132 | 1.03 (5) |
N1—C082 | 1.47 (5) | C082—C092 | 1.65 (8) |
N1—C092 | 1.81 (5) | C092—C102 | 1.47 (6) |
N2—C091 | 1.15 (4) | C102—C112 | 1.35 (5) |
N2—C09 | 1.67 (2) | C102—H102 | 0.9300 |
O1—C092 | 1.72 (4) | C112—C122 | 1.16 (12) |
C08—C13 | 1.34 (3) | C112—H112 | 0.9300 |
C08—C09 | 1.52 (3) | C122—C132 | 1.51 (8) |
C09—C10 | 1.29 (2) | C122—H122 | 0.9300 |
C10—C11 | 1.33 (2) | C132—H132 | 0.9300 |
| | | |
C02—C01—C03 | 121.7 (7) | C11—C12—C13 | 125 (2) |
C02—C01—C06 | 117.4 (9) | C11—C12—H12 | 117.6 |
C03—C01—C06 | 120.9 (7) | C13—C12—H12 | 117.6 |
C01—C02—C05i | 119.3 (8) | C08—C13—C12 | 114 (2) |
C01—C02—H02 | 121 (3) | C08—C13—H13 | 123.2 |
C05i—C02—H02 | 120 (3) | C12—C13—H13 | 123.2 |
C01—C03—C04 | 121.9 (6) | N1—C081—C091 | 111 (2) |
C01—C03—C03i | 118.1 (9) | N1—C081—C131 | 119 (3) |
C04—C03—C03i | 120.0 (9) | C091—C081—C131 | 128 (3) |
C05—C04—C03 | 120.8 (7) | N2—C091—C101 | 139 (3) |
C05—C04—C07 | 121.6 (8) | N2—C091—C081 | 106 (3) |
C03—C04—C07 | 117.5 (8) | C101—C091—C081 | 114 (3) |
C04—C05—C02i | 120.0 (8) | C111—C101—C091 | 121 (3) |
C04—C05—H05 | 130 (3) | C111—C101—H101 | 119.7 |
C02i—C05—H05 | 110 (3) | C091—C101—H101 | 119.7 |
O1—C06—N1 | 118.9 (9) | C121—C111—C101 | 125 (3) |
O1—C06—C01 | 125.2 (9) | C121—C111—H111 | 117.7 |
N1—C06—C01 | 115.9 (8) | C101—C111—H111 | 117.7 |
N2—C07—N1 | 117.4 (8) | C111—C121—C131 | 129 (3) |
N2—C07—C04 | 123.3 (11) | C111—C121—H121 | 115.6 |
N1—C07—C04 | 119.3 (8) | C131—C121—H121 | 115.6 |
C081—N1—C07 | 94.3 (16) | C121—C131—C081 | 102 (3) |
C081—N1—C06 | 140.9 (18) | C121—C131—H131 | 129.0 |
C07—N1—C06 | 124.5 (7) | C081—C131—H131 | 129.0 |
C07—N1—C08 | 120.9 (10) | C132—C082—N1 | 160 (5) |
C06—N1—C08 | 114.6 (11) | C132—C082—C092 | 105 (6) |
C07—N1—C082 | 99 (3) | N1—C082—C092 | 71 (3) |
C06—N1—C082 | 135 (3) | C102—C092—C082 | 111 (4) |
C091—N2—C07 | 109.8 (17) | C102—C092—O1 | 118 (3) |
C07—N2—C09 | 94.9 (8) | C082—C092—O1 | 129 (3) |
C06—O1—C092 | 83.9 (16) | C112—C102—C092 | 121 (4) |
C13—C08—N1 | 147 (2) | C112—C102—H102 | 119.5 |
C13—C08—C09 | 122 (2) | C092—C102—H102 | 119.5 |
N1—C08—C09 | 90.8 (14) | C122—C112—C102 | 122 (4) |
C10—C09—C08 | 116.8 (17) | C122—C112—H112 | 119.2 |
C10—C09—N2 | 127 (2) | C102—C112—H112 | 119.2 |
C08—C09—N2 | 116.0 (13) | C112—C122—C132 | 113 (6) |
C09—C10—C11 | 126 (2) | C112—C122—H122 | 123.3 |
C09—C10—H10 | 117.2 | C132—C122—H122 | 123.3 |
C11—C10—H10 | 117.2 | C082—C132—C122 | 136 (7) |
C10—C11—C12 | 117 (2) | C082—C132—H132 | 112.1 |
C10—C11—H11 | 121.5 | C122—C132—H132 | 112.1 |
C12—C11—H11 | 121.5 | | |
| | | |
C03—C01—C02—C05i | 0.7 (9) | C06—N1—C081—C131 | 14 (4) |
C06—C01—C02—C05i | −179.6 (5) | C08—N1—C081—C131 | −5 (2) |
C02—C01—C03—C04 | −179.8 (5) | C082—N1—C081—C131 | −61 (14) |
C06—C01—C03—C04 | 0.6 (8) | C092—N1—C081—C131 | 5 (2) |
C02—C01—C03—C03i | −1.5 (9) | C06—N1—C081—C07 | −173.0 (18) |
C06—C01—C03—C03i | 178.8 (6) | C08—N1—C081—C07 | 167 (3) |
C01—C03—C04—C05 | 179.3 (6) | C082—N1—C081—C07 | 112 (15) |
C03i—C03—C04—C05 | 1.1 (9) | C092—N1—C081—C07 | 178.1 (13) |
C01—C03—C04—C07 | −1.0 (7) | N2—C07—C081—N1 | −175.8 (12) |
C03i—C03—C04—C07 | −179.2 (6) | C04—C07—C081—N1 | 16 (4) |
C03—C04—C05—C02i | −0.2 (9) | C091—C07—C081—N1 | −171 (2) |
C07—C04—C05—C02i | −180.0 (5) | N2—C07—C081—C091 | −5.1 (11) |
C02—C01—C06—O1 | −0.5 (9) | N1—C07—C081—C091 | 171 (2) |
C03—C01—C06—O1 | 179.2 (7) | C04—C07—C081—C091 | −173 (2) |
C02—C01—C06—N1 | −179.3 (5) | N2—C07—C081—C131 | −156 (7) |
C03—C01—C06—N1 | 0.3 (8) | N1—C07—C081—C131 | 20 (6) |
C05—C04—C07—N2 | 1.5 (9) | C04—C07—C081—C131 | 36 (9) |
C03—C04—C07—N2 | −178.3 (5) | C091—C07—C081—C131 | −151 (8) |
C05—C04—C07—N1 | −179.8 (6) | C07—N2—C091—C101 | −179 (3) |
C03—C04—C07—N1 | 0.5 (7) | C09—N2—C091—C101 | −172 (8) |
C05—C04—C07—C091 | −1 (2) | C07—N2—C091—C081 | −9 (2) |
C03—C04—C07—C091 | 179.2 (18) | C09—N2—C091—C081 | −3 (4) |
C05—C04—C07—C081 | 168 (3) | C09—N2—C091—C07 | 6 (6) |
C03—C04—C07—C081 | −12 (3) | N1—C081—C091—N2 | 13 (3) |
N2—C07—N1—C081 | 4.6 (13) | C131—C081—C091—N2 | 174 (2) |
C04—C07—N1—C081 | −174.2 (13) | C07—C081—C091—N2 | 5.8 (13) |
C091—C07—N1—C081 | 6.3 (14) | N1—C081—C091—C101 | −174.7 (19) |
N2—C07—N1—C06 | 179.2 (5) | C131—C081—C091—C101 | −13 (4) |
C04—C07—N1—C06 | 0.4 (8) | C07—C081—C091—C101 | 178.4 (19) |
C091—C07—N1—C06 | −179.0 (8) | N1—C081—C091—C07 | 6.8 (14) |
C081—C07—N1—C06 | 174.7 (14) | C131—C081—C091—C07 | 168 (3) |
N2—C07—N1—C08 | −2.1 (10) | N1—C07—C091—N2 | −177.2 (12) |
C04—C07—N1—C08 | 179.1 (8) | C04—C07—C091—N2 | 4 (3) |
C091—C07—N1—C08 | −0.4 (10) | C081—C07—C091—N2 | −171 (2) |
C081—C07—N1—C08 | −6.7 (16) | N2—C07—C091—C081 | 171 (2) |
N2—C07—N1—C082 | −9 (2) | N1—C07—C091—C081 | −6.3 (13) |
C04—C07—N1—C082 | 172 (2) | C04—C07—C091—C081 | 174.8 (17) |
C091—C07—N1—C082 | −7 (2) | N2—C091—C101—C111 | 177 (3) |
C081—C07—N1—C082 | −14 (2) | C081—C091—C101—C111 | 7 (3) |
N2—C07—N1—C092 | 0 (3) | C091—C101—C111—C121 | −7 (3) |
C04—C07—N1—C092 | −179 (3) | C101—C111—C121—C131 | 11 (4) |
C091—C07—N1—C092 | 2 (3) | C111—C121—C131—C081 | −13 (4) |
C081—C07—N1—C092 | −5 (3) | N1—C081—C131—C121 | 175 (2) |
O1—C06—N1—C081 | −8 (2) | C091—C081—C131—C121 | 15 (4) |
C01—C06—N1—C081 | 171 (2) | C07—C081—C131—C121 | 159 (6) |
C092—C06—N1—C081 | −8 (2) | C081—N1—C082—C132 | 26 (13) |
O1—C06—N1—C07 | −179.7 (6) | C07—N1—C082—C132 | 96 (22) |
C01—C06—N1—C07 | −0.8 (8) | C06—N1—C082—C132 | −94 (22) |
C092—C06—N1—C07 | −179.8 (12) | C08—N1—C082—C132 | −68 (19) |
O1—C06—N1—C08 | 1.5 (10) | C092—N1—C082—C132 | −81 (22) |
C01—C06—N1—C08 | −179.6 (8) | C081—N1—C082—C092 | 106 (15) |
C092—C06—N1—C08 | 1.5 (14) | C07—N1—C082—C092 | 176.2 (14) |
O1—C06—N1—C082 | 12 (3) | C06—N1—C082—C092 | −14 (3) |
C01—C06—N1—C082 | −169 (3) | C08—N1—C082—C092 | 12 (5) |
C092—C06—N1—C082 | 12 (3) | C132—C082—C092—C102 | −23 (5) |
O1—C06—N1—C092 | 0.0 (13) | N1—C082—C092—C102 | 177 (3) |
C01—C06—N1—C092 | 178.9 (12) | C132—C082—C092—O1 | 172 (4) |
N1—C07—N2—C091 | 3.2 (14) | N1—C082—C092—O1 | 12 (3) |
C04—C07—N2—C091 | −178.1 (13) | C132—C082—C092—N1 | 160 (5) |
C081—C07—N2—C091 | 6.4 (15) | C132—C082—C092—C06 | 166 (4) |
N1—C07—N2—C09 | 1.5 (7) | N1—C082—C092—C06 | 6.5 (16) |
C04—C07—N2—C09 | −179.7 (6) | C06—O1—C092—C102 | −173 (3) |
C091—C07—N2—C09 | −1.7 (15) | C06—O1—C092—C082 | −10 (3) |
C081—C07—N2—C09 | 4.7 (10) | C06—O1—C092—N1 | 0.0 (9) |
N1—C06—O1—C092 | 0.0 (13) | C081—N1—C092—C102 | −24 (8) |
C01—C06—O1—C092 | −178.8 (12) | C07—N1—C092—C102 | −19 (10) |
C081—N1—C08—C13 | 167 (5) | C06—N1—C092—C102 | 162 (8) |
C07—N1—C08—C13 | −178 (2) | C08—N1—C092—C102 | −16 (7) |
C06—N1—C08—C13 | 1 (3) | C082—N1—C092—C102 | −8 (8) |
C082—N1—C08—C13 | −160 (8) | C081—N1—C092—C082 | −15 (3) |
C092—N1—C08—C13 | 3 (3) | C07—N1—C092—C082 | −10 (4) |
C081—N1—C08—C09 | −13 (3) | C06—N1—C092—C082 | 170 (2) |
C07—N1—C08—C09 | 1.1 (12) | C08—N1—C092—C082 | −8 (3) |
C06—N1—C08—C09 | 179.9 (7) | C081—N1—C092—O1 | 174.2 (19) |
C082—N1—C08—C09 | 19 (6) | C07—N1—C092—O1 | 179 (2) |
C092—N1—C08—C09 | −178 (2) | C06—N1—C092—O1 | 0.0 (8) |
C13—C08—C09—C10 | −1 (2) | C08—N1—C092—O1 | −178 (3) |
N1—C08—C09—C10 | 179.0 (11) | C082—N1—C092—O1 | −170 (3) |
C13—C08—C09—N2 | 179.4 (14) | C081—N1—C092—C06 | 174.3 (15) |
N1—C08—C09—N2 | −0.1 (12) | C07—N1—C092—C06 | 179 (3) |
C091—N2—C09—C10 | 6 (5) | C08—N1—C092—C06 | −178 (2) |
C07—N2—C09—C10 | −179.8 (13) | C082—N1—C092—C06 | −170 (2) |
C091—N2—C09—C08 | −175 (6) | O1—C06—C092—C102 | 14 (6) |
C07—N2—C09—C08 | −0.8 (11) | N1—C06—C092—C102 | −166 (7) |
C08—C09—C10—C11 | −2 (2) | O1—C06—C092—C082 | 173 (2) |
N2—C09—C10—C11 | 177.3 (10) | N1—C06—C092—C082 | −7.4 (18) |
C09—C10—C11—C12 | 1 (2) | N1—C06—C092—O1 | 180.0 (13) |
C10—C11—C12—C13 | 2 (3) | O1—C06—C092—N1 | −180.0 (13) |
N1—C08—C13—C12 | −176 (2) | C082—C092—C102—C112 | 14 (4) |
C09—C08—C13—C12 | 4 (3) | O1—C092—C102—C112 | −179 (3) |
C11—C12—C13—C08 | −5 (3) | N1—C092—C102—C112 | 21 (10) |
C07—N1—C081—C091 | −9.3 (19) | C06—C092—C102—C112 | 171 (5) |
C06—N1—C081—C091 | 177.7 (11) | C092—C102—C112—C122 | −17 (6) |
C08—N1—C081—C091 | 158 (5) | C102—C112—C122—C132 | 21 (7) |
C082—N1—C081—C091 | 102 (16) | N1—C082—C132—C122 | 115 (20) |
C092—N1—C081—C091 | 169 (3) | C092—C082—C132—C122 | 40 (8) |
C07—N1—C081—C131 | −173 (2) | C112—C122—C132—C082 | −43 (10) |
Symmetry code: (i) −x+1, −y+1, −z+1. |