Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107065743/bm5050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050IVsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050Vsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050VIIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050IXsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050XIVsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107065743/bm5050XVsup7.hkl |
CCDC references: 679947; 679948; 679949; 679950; 679951; 679952
For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003 & SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 & PRPKAPPA (Ferguson, 1999).
C27H20ClN3 | F(000) = 880 |
Mr = 421.91 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4752 reflections |
a = 12.1072 (4) Å | θ = 2.3–27.5° |
b = 14.2672 (5) Å | µ = 0.21 mm−1 |
c = 12.7635 (4) Å | T = 120 K |
β = 109.953 (8)° | Lath, colourless |
V = 2072.37 (16) Å3 | 0.38 × 0.38 × 0.10 mm |
Z = 4 |
Bruker-Nonius KappaCCD diffractometer | 4752 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 3209 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
ϕ & ω scans | h = −15→15 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −18→18 |
Tmin = 0.936, Tmax = 0.980 | l = −16→16 |
23840 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.6125P] where P = (Fo2 + 2Fc2)/3 |
4752 reflections | (Δ/σ)max = 0.001 |
281 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C27H20ClN3 | V = 2072.37 (16) Å3 |
Mr = 421.91 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1072 (4) Å | µ = 0.21 mm−1 |
b = 14.2672 (5) Å | T = 120 K |
c = 12.7635 (4) Å | 0.38 × 0.38 × 0.10 mm |
β = 109.953 (8)° |
Bruker-Nonius KappaCCD diffractometer | 4752 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 3209 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.980 | Rint = 0.052 |
23840 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.58 e Å−3 |
4752 reflections | Δρmin = −0.43 e Å−3 |
281 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.00744 (18) | 0.36013 (13) | −0.16474 (15) | 0.0294 (4) | |
C2 | 0.03741 (19) | 0.36595 (13) | −0.25987 (16) | 0.0329 (5) | |
C3 | 0.14616 (19) | 0.40119 (14) | −0.25367 (16) | 0.0352 (5) | |
C4 | 0.22395 (18) | 0.43202 (15) | −0.15249 (16) | 0.0344 (5) | |
C4A | 0.19546 (17) | 0.42682 (13) | −0.05568 (15) | 0.0284 (4) | |
C5 | 0.27633 (18) | 0.46297 (16) | 0.05400 (17) | 0.0372 (5) | |
C6 | 0.26683 (19) | 0.40943 (17) | 0.14916 (17) | 0.0421 (5) | |
C6A | 0.14236 (16) | 0.39944 (13) | 0.14617 (15) | 0.0283 (4) | |
C7 | 0.11145 (17) | 0.39896 (13) | 0.24182 (15) | 0.0260 (4) | |
C71 | 0.19864 (16) | 0.41941 (13) | 0.35436 (15) | 0.0266 (4) | |
C72 | 0.23025 (17) | 0.35070 (14) | 0.43661 (15) | 0.0301 (4) | |
C73 | 0.30911 (18) | 0.36985 (14) | 0.54142 (16) | 0.0332 (5) | |
C74 | 0.35735 (17) | 0.45859 (15) | 0.56445 (15) | 0.0318 (5) | |
Cl74 | 0.45535 (5) | 0.48281 (5) | 0.69740 (4) | 0.04818 (19) | |
C75 | 0.32950 (18) | 0.52784 (14) | 0.48396 (16) | 0.0348 (5) | |
C76 | 0.24985 (18) | 0.50754 (14) | 0.37932 (16) | 0.0324 (5) | |
C7A | −0.00574 (16) | 0.37700 (12) | 0.22819 (14) | 0.0234 (4) | |
C8 | −0.07678 (16) | 0.36835 (12) | 0.29704 (15) | 0.0257 (4) | |
C81 | −0.04571 (18) | 0.38328 (14) | 0.41953 (15) | 0.0314 (5) | |
N9 | −0.18497 (14) | 0.34299 (11) | 0.23761 (12) | 0.0284 (4) | |
N10 | −0.18927 (13) | 0.33480 (11) | 0.12828 (12) | 0.0267 (4) | |
C101 | −0.29791 (16) | 0.31238 (13) | 0.04437 (15) | 0.0263 (4) | |
C102 | −0.40149 (17) | 0.32705 (14) | 0.06538 (16) | 0.0326 (5) | |
C103 | −0.50762 (18) | 0.30409 (16) | −0.01550 (16) | 0.0379 (5) | |
C104 | −0.51116 (19) | 0.26809 (16) | −0.11708 (17) | 0.0398 (5) | |
C105 | −0.40778 (19) | 0.25512 (15) | −0.13796 (17) | 0.0390 (5) | |
C106 | −0.30061 (17) | 0.27617 (14) | −0.05773 (16) | 0.0321 (5) | |
C10A | −0.08189 (16) | 0.35651 (12) | 0.12001 (14) | 0.0240 (4) | |
N11 | −0.05666 (13) | 0.36025 (10) | 0.02614 (12) | 0.0245 (3) | |
C11A | 0.05456 (16) | 0.38283 (12) | 0.04048 (15) | 0.0241 (4) | |
C11B | 0.08613 (16) | 0.38955 (12) | −0.06186 (15) | 0.0250 (4) | |
H1 | −0.0672 | 0.3360 | −0.1694 | 0.035* | |
H2 | −0.0165 | 0.3458 | −0.3295 | 0.039* | |
H3 | 0.1673 | 0.4042 | −0.3188 | 0.042* | |
H4 | 0.2978 | 0.4571 | −0.1490 | 0.041* | |
H5A | 0.3583 | 0.4598 | 0.0549 | 0.045* | |
H5B | 0.2577 | 0.5296 | 0.0620 | 0.045* | |
H6A | 0.3136 | 0.4412 | 0.2192 | 0.050* | |
H6B | 0.3008 | 0.3463 | 0.1494 | 0.050* | |
H72 | 0.1971 | 0.2898 | 0.4204 | 0.036* | |
H73 | 0.3300 | 0.3226 | 0.5972 | 0.040* | |
H75 | 0.3643 | 0.5882 | 0.5001 | 0.042* | |
H76 | 0.2298 | 0.5548 | 0.3235 | 0.039* | |
H81A | −0.1174 | 0.3954 | 0.4367 | 0.047* | |
H81B | 0.0074 | 0.4371 | 0.4428 | 0.047* | |
H81C | −0.0068 | 0.3271 | 0.4595 | 0.047* | |
H102 | −0.3998 | 0.3526 | 0.1346 | 0.039* | |
H103 | −0.5788 | 0.3132 | −0.0010 | 0.045* | |
H104 | −0.5843 | 0.2524 | −0.1721 | 0.048* | |
H105 | −0.4101 | 0.2314 | −0.2083 | 0.047* | |
H106 | −0.2296 | 0.2660 | −0.0722 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0334 (11) | 0.0296 (10) | 0.0257 (10) | −0.0030 (8) | 0.0109 (9) | −0.0014 (8) |
C2 | 0.0429 (13) | 0.0330 (11) | 0.0233 (10) | 0.0018 (9) | 0.0121 (9) | −0.0001 (8) |
C3 | 0.0449 (13) | 0.0385 (11) | 0.0293 (10) | 0.0067 (10) | 0.0220 (10) | 0.0053 (9) |
C4 | 0.0300 (11) | 0.0423 (12) | 0.0350 (11) | 0.0028 (9) | 0.0165 (9) | 0.0060 (9) |
C4A | 0.0273 (10) | 0.0303 (10) | 0.0303 (10) | 0.0040 (8) | 0.0132 (8) | 0.0029 (8) |
C5 | 0.0285 (12) | 0.0497 (13) | 0.0354 (11) | −0.0056 (10) | 0.0135 (9) | 0.0019 (9) |
C6 | 0.0308 (12) | 0.0638 (15) | 0.0326 (11) | −0.0105 (11) | 0.0122 (9) | −0.0069 (10) |
C6A | 0.0249 (10) | 0.0345 (10) | 0.0253 (9) | −0.0026 (8) | 0.0083 (8) | −0.0023 (8) |
C7 | 0.0271 (11) | 0.0264 (9) | 0.0234 (9) | −0.0007 (8) | 0.0071 (8) | −0.0012 (7) |
C71 | 0.0210 (10) | 0.0347 (11) | 0.0247 (9) | −0.0020 (8) | 0.0086 (8) | −0.0022 (8) |
C72 | 0.0289 (11) | 0.0319 (10) | 0.0291 (10) | −0.0030 (8) | 0.0094 (8) | −0.0022 (8) |
C73 | 0.0321 (11) | 0.0400 (12) | 0.0274 (10) | 0.0012 (9) | 0.0099 (9) | 0.0049 (9) |
C74 | 0.0213 (10) | 0.0506 (13) | 0.0223 (9) | −0.0039 (9) | 0.0060 (8) | −0.0033 (9) |
Cl74 | 0.0384 (3) | 0.0722 (4) | 0.0264 (3) | −0.0131 (3) | 0.0014 (2) | −0.0056 (3) |
C75 | 0.0320 (12) | 0.0375 (11) | 0.0328 (11) | −0.0088 (9) | 0.0084 (9) | −0.0065 (9) |
C76 | 0.0320 (12) | 0.0348 (11) | 0.0280 (10) | −0.0024 (9) | 0.0072 (9) | 0.0015 (8) |
C7A | 0.0250 (10) | 0.0230 (9) | 0.0222 (9) | 0.0000 (8) | 0.0078 (8) | 0.0006 (7) |
C8 | 0.0274 (11) | 0.0262 (9) | 0.0241 (9) | −0.0005 (8) | 0.0094 (8) | −0.0005 (7) |
C81 | 0.0310 (11) | 0.0404 (12) | 0.0241 (10) | −0.0052 (9) | 0.0109 (8) | −0.0034 (8) |
N9 | 0.0301 (9) | 0.0347 (9) | 0.0224 (8) | −0.0015 (7) | 0.0114 (7) | −0.0005 (7) |
N10 | 0.0233 (9) | 0.0360 (9) | 0.0217 (8) | −0.0041 (7) | 0.0086 (7) | −0.0008 (7) |
C101 | 0.0240 (10) | 0.0293 (10) | 0.0237 (9) | −0.0039 (8) | 0.0055 (8) | 0.0026 (8) |
C102 | 0.0280 (11) | 0.0443 (12) | 0.0267 (10) | −0.0027 (9) | 0.0110 (9) | 0.0018 (9) |
C103 | 0.0241 (11) | 0.0541 (13) | 0.0345 (11) | −0.0026 (10) | 0.0088 (9) | 0.0056 (10) |
C104 | 0.0276 (12) | 0.0521 (14) | 0.0327 (11) | −0.0077 (10) | 0.0014 (9) | 0.0000 (10) |
C105 | 0.0382 (13) | 0.0469 (13) | 0.0291 (11) | −0.0078 (10) | 0.0082 (9) | −0.0066 (9) |
C106 | 0.0262 (11) | 0.0384 (11) | 0.0316 (11) | −0.0032 (9) | 0.0099 (9) | −0.0050 (9) |
C10A | 0.0247 (10) | 0.0255 (9) | 0.0230 (9) | −0.0007 (8) | 0.0098 (8) | −0.0001 (7) |
N11 | 0.0240 (8) | 0.0261 (8) | 0.0239 (8) | 0.0004 (7) | 0.0089 (6) | 0.0000 (6) |
C11A | 0.0250 (10) | 0.0220 (9) | 0.0264 (9) | 0.0007 (8) | 0.0104 (8) | 0.0000 (7) |
C11B | 0.0293 (11) | 0.0226 (9) | 0.0256 (9) | 0.0025 (8) | 0.0126 (8) | −0.0002 (7) |
C1—C2 | 1.383 (3) | C74—Cl74 | 1.7415 (19) |
C1—C11B | 1.398 (3) | C75—C76 | 1.385 (3) |
C1—H1 | 0.95 | C75—H75 | 0.95 |
C2—C3 | 1.386 (3) | C76—H76 | 0.95 |
C2—H2 | 0.95 | C7A—C10A | 1.405 (2) |
C3—C4 | 1.385 (3) | C7A—C8 | 1.429 (2) |
C3—H3 | 0.95 | C8—N9 | 1.321 (2) |
C4—C4A | 1.394 (3) | C8—C81 | 1.493 (2) |
C4—H4 | 0.95 | C81—H81A | 0.98 |
C4A—C11B | 1.404 (3) | C81—H81B | 0.98 |
C4A—C5 | 1.500 (3) | C81—H81C | 0.98 |
C5—C6 | 1.472 (3) | N9—N10 | 1.384 (2) |
C5—H5A | 0.99 | N10—C10A | 1.375 (2) |
C5—H5B | 0.99 | N10—C101 | 1.420 (2) |
C6—C6A | 1.501 (3) | C101—C102 | 1.385 (3) |
C6—H6A | 0.99 | C101—C106 | 1.392 (3) |
C6—H6B | 0.99 | C102—C103 | 1.385 (3) |
C6A—C7 | 1.394 (2) | C102—H102 | 0.95 |
C6A—C11A | 1.424 (3) | C103—C104 | 1.381 (3) |
C7—C7A | 1.405 (3) | C103—H103 | 0.95 |
C7—C71 | 1.493 (2) | C104—C105 | 1.378 (3) |
C71—C76 | 1.390 (3) | C104—H104 | 0.95 |
C71—C72 | 1.391 (3) | C105—C106 | 1.384 (3) |
C72—C73 | 1.380 (3) | C105—H105 | 0.95 |
C72—H72 | 0.95 | C106—H106 | 0.95 |
C73—C74 | 1.383 (3) | C10A—N11 | 1.335 (2) |
C73—H73 | 0.95 | N11—C11A | 1.335 (2) |
C74—C75 | 1.382 (3) | C11A—C11B | 1.484 (2) |
C2—C1—C11B | 120.51 (19) | C75—C76—C71 | 121.29 (18) |
C2—C1—H1 | 119.7 | C75—C76—H76 | 119.4 |
C11B—C1—H1 | 119.7 | C71—C76—H76 | 119.4 |
C1—C2—C3 | 120.01 (18) | C10A—C7A—C7 | 117.68 (16) |
C1—C2—H2 | 120.0 | C10A—C7A—C8 | 104.81 (16) |
C3—C2—H2 | 120.0 | C7—C7A—C8 | 137.51 (17) |
C4—C3—C2 | 119.92 (18) | N9—C8—C7A | 110.95 (16) |
C4—C3—H3 | 120.0 | N9—C8—C81 | 119.12 (17) |
C2—C3—H3 | 120.0 | C7A—C8—C81 | 129.93 (17) |
C3—C4—C4A | 120.97 (19) | C8—C81—H81A | 109.5 |
C3—C4—H4 | 119.5 | C8—C81—H81B | 109.5 |
C4A—C4—H4 | 119.5 | H81A—C81—H81B | 109.5 |
C4—C4A—C11B | 118.97 (18) | C8—C81—H81C | 109.5 |
C4—C4A—C5 | 121.94 (18) | H81A—C81—H81C | 109.5 |
C11B—C4A—C5 | 119.05 (16) | H81B—C81—H81C | 109.5 |
C6—C5—C4A | 112.45 (18) | C8—N9—N10 | 106.92 (15) |
C6—C5—H5A | 109.1 | C10A—N10—N9 | 110.31 (14) |
C4A—C5—H5A | 109.1 | C10A—N10—C101 | 130.49 (15) |
C6—C5—H5B | 109.1 | N9—N10—C101 | 119.07 (15) |
C4A—C5—H5B | 109.1 | C102—C101—C106 | 120.26 (17) |
H5A—C5—H5B | 107.8 | C102—C101—N10 | 119.12 (16) |
C5—C6—C6A | 112.87 (18) | C106—C101—N10 | 120.62 (17) |
C5—C6—H6A | 109.0 | C101—C102—C103 | 119.40 (18) |
C6A—C6—H6A | 109.0 | C101—C102—H102 | 120.3 |
C5—C6—H6B | 109.0 | C103—C102—H102 | 120.3 |
C6A—C6—H6B | 109.0 | C104—C103—C102 | 120.7 (2) |
H6A—C6—H6B | 107.8 | C104—C103—H103 | 119.6 |
C7—C6A—C11A | 119.49 (17) | C102—C103—H103 | 119.6 |
C7—C6A—C6 | 123.06 (17) | C105—C104—C103 | 119.47 (19) |
C11A—C6A—C6 | 117.28 (16) | C105—C104—H104 | 120.3 |
C6A—C7—C7A | 117.03 (16) | C103—C104—H104 | 120.3 |
C6A—C7—C71 | 121.93 (17) | C104—C105—C106 | 120.78 (19) |
C7A—C7—C71 | 121.03 (16) | C104—C105—H105 | 119.6 |
C76—C71—C72 | 118.57 (17) | C106—C105—H105 | 119.6 |
C76—C71—C7 | 120.73 (17) | C105—C106—C101 | 119.33 (19) |
C72—C71—C7 | 120.70 (17) | C105—C106—H106 | 120.3 |
C73—C72—C71 | 120.88 (18) | C101—C106—H106 | 120.3 |
C73—C72—H72 | 119.6 | N11—C10A—N10 | 126.14 (16) |
C71—C72—H72 | 119.6 | N11—C10A—C7A | 126.84 (17) |
C72—C73—C74 | 119.31 (18) | N10—C10A—C7A | 106.98 (15) |
C72—C73—H73 | 120.3 | C10A—N11—C11A | 114.56 (15) |
C74—C73—H73 | 120.3 | N11—C11A—C6A | 124.20 (16) |
C75—C74—C73 | 121.22 (18) | N11—C11A—C11B | 116.46 (16) |
C75—C74—Cl74 | 119.66 (16) | C6A—C11A—C11B | 119.33 (16) |
C73—C74—Cl74 | 119.12 (15) | C1—C11B—C4A | 119.60 (17) |
C74—C75—C76 | 118.71 (18) | C1—C11B—C11A | 120.64 (17) |
C74—C75—H75 | 120.6 | C4A—C11B—C11A | 119.76 (16) |
C76—C75—H75 | 120.6 | ||
C11B—C1—C2—C3 | 0.0 (3) | C8—N9—N10—C101 | −177.04 (16) |
C1—C2—C3—C4 | −1.1 (3) | C10A—N10—C101—C102 | −156.04 (19) |
C2—C3—C4—C4A | 1.1 (3) | N9—N10—C101—C102 | 19.5 (3) |
C3—C4—C4A—C11B | 0.1 (3) | C10A—N10—C101—C106 | 23.9 (3) |
C3—C4—C4A—C5 | −177.72 (19) | N9—N10—C101—C106 | −160.51 (17) |
C4—C4A—C5—C6 | −148.6 (2) | C106—C101—C102—C103 | 0.9 (3) |
C11B—C4A—C5—C6 | 33.6 (3) | N10—C101—C102—C103 | −179.09 (18) |
C4A—C5—C6—C6A | −51.1 (3) | C101—C102—C103—C104 | −0.9 (3) |
C5—C6—C6A—C7 | −145.1 (2) | C102—C103—C104—C105 | −0.1 (3) |
C5—C6—C6A—C11A | 39.7 (3) | C103—C104—C105—C106 | 1.1 (3) |
C11A—C6A—C7—C7A | 3.2 (3) | C104—C105—C106—C101 | −1.1 (3) |
C6—C6A—C7—C7A | −171.97 (19) | C102—C101—C106—C105 | 0.1 (3) |
C11A—C6A—C7—C71 | −177.70 (17) | N10—C101—C106—C105 | −179.90 (18) |
C6—C6A—C7—C71 | 7.2 (3) | N9—N10—C10A—N11 | −176.53 (16) |
C6A—C7—C71—C76 | 65.2 (3) | C101—N10—C10A—N11 | −0.7 (3) |
C7A—C7—C71—C76 | −115.7 (2) | N9—N10—C10A—C7A | 1.47 (19) |
C6A—C7—C71—C72 | −114.9 (2) | C101—N10—C10A—C7A | 177.33 (18) |
C7A—C7—C71—C72 | 64.2 (2) | C7—C7A—C10A—N11 | −3.8 (3) |
C76—C71—C72—C73 | 1.1 (3) | C8—C7A—C10A—N11 | 176.34 (17) |
C7—C71—C72—C73 | −178.73 (17) | C7—C7A—C10A—N10 | 178.26 (16) |
C71—C72—C73—C74 | −0.2 (3) | C8—C7A—C10A—N10 | −1.65 (19) |
C72—C73—C74—C75 | −1.1 (3) | N10—C10A—N11—C11A | −179.83 (17) |
C72—C73—C74—Cl74 | 179.17 (15) | C7A—C10A—N11—C11A | 2.6 (3) |
C73—C74—C75—C76 | 1.3 (3) | C10A—N11—C11A—C6A | 1.7 (2) |
Cl74—C74—C75—C76 | −178.93 (15) | C10A—N11—C11A—C11B | −178.91 (15) |
C74—C75—C76—C71 | −0.3 (3) | C7—C6A—C11A—N11 | −4.6 (3) |
C72—C71—C76—C75 | −0.9 (3) | C6—C6A—C11A—N11 | 170.78 (18) |
C7—C71—C76—C75 | 178.99 (18) | C7—C6A—C11A—C11B | 176.02 (16) |
C6A—C7—C7A—C10A | 0.6 (2) | C6—C6A—C11A—C11B | −8.6 (3) |
C71—C7—C7A—C10A | −178.58 (16) | C2—C1—C11B—C4A | 1.2 (3) |
C6A—C7—C7A—C8 | −179.6 (2) | C2—C1—C11B—C11A | −179.60 (17) |
C71—C7—C7A—C8 | 1.3 (3) | C4—C4A—C11B—C1 | −1.2 (3) |
C10A—C7A—C8—N9 | 1.3 (2) | C5—C4A—C11B—C1 | 176.68 (17) |
C7—C7A—C8—N9 | −178.6 (2) | C4—C4A—C11B—C11A | 179.57 (17) |
C10A—C7A—C8—C81 | −178.79 (18) | C5—C4A—C11B—C11A | −2.6 (3) |
C7—C7A—C8—C81 | 1.3 (4) | N11—C11A—C11B—C1 | −9.1 (2) |
C7A—C8—N9—N10 | −0.4 (2) | C6A—C11A—C11B—C1 | 170.34 (17) |
C81—C8—N9—N10 | 179.66 (15) | N11—C11A—C11B—C4A | 170.16 (17) |
C8—N9—N10—C10A | −0.64 (19) | C6A—C11A—C11B—C4A | −10.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···Cg1i | 0.95 | 2.88 | 3.823 (2) | 170 |
C75—H75···Cg2ii | 0.95 | 2.94 | 3.860 (2) | 164 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2. |
C26H20N4 | F(000) = 816 |
Mr = 388.46 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4456 reflections |
a = 11.2274 (6) Å | θ = 3.0–27.5° |
b = 13.7079 (8) Å | µ = 0.08 mm−1 |
c = 12.6935 (7) Å | T = 120 K |
β = 95.731 (3)° | Plate, colourless |
V = 1943.82 (19) Å3 | 0.12 × 0.10 × 0.02 mm |
Z = 4 |
Bruker-Nonius KappaCCD diffractometer | 4456 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2654 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.085 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ & ω scans | h = −14→14 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −17→17 |
Tmin = 0.987, Tmax = 0.998 | l = −16→16 |
19684 measured reflections |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.9505P] where P = (Fo2 + 2Fc2)/3 |
4456 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C26H20N4 | V = 1943.82 (19) Å3 |
Mr = 388.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2274 (6) Å | µ = 0.08 mm−1 |
b = 13.7079 (8) Å | T = 120 K |
c = 12.6935 (7) Å | 0.12 × 0.10 × 0.02 mm |
β = 95.731 (3)° |
Bruker-Nonius KappaCCD diffractometer | 4456 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2654 reflections with I > 2σ(I) |
Tmin = 0.987, Tmax = 0.998 | Rint = 0.085 |
19684 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.23 e Å−3 |
4456 reflections | Δρmin = −0.21 e Å−3 |
272 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4652 (2) | 0.36294 (16) | 0.28142 (19) | 0.0278 (6) | |
C2 | 0.4340 (2) | 0.35731 (17) | 0.1738 (2) | 0.0311 (6) | |
C3 | 0.3149 (2) | 0.36973 (18) | 0.1334 (2) | 0.0348 (6) | |
C4 | 0.2294 (2) | 0.38661 (18) | 0.2018 (2) | 0.0331 (6) | |
C4A | 0.2587 (2) | 0.39087 (17) | 0.31112 (19) | 0.0284 (6) | |
C5 | 0.1640 (2) | 0.3974 (2) | 0.3862 (2) | 0.0361 (6) | |
C6 | 0.2067 (2) | 0.44836 (18) | 0.48871 (19) | 0.0292 (6) | |
C6A | 0.3282 (2) | 0.41464 (16) | 0.53671 (19) | 0.0230 (5) | |
C7 | 0.3622 (2) | 0.41736 (16) | 0.64524 (19) | 0.0249 (6) | |
C71 | 0.27679 (19) | 0.44442 (17) | 0.72279 (18) | 0.0231 (5) | |
C72 | 0.2492 (2) | 0.37679 (18) | 0.79790 (19) | 0.0276 (6) | |
N73 | 0.17335 (18) | 0.39308 (16) | 0.87091 (16) | 0.0355 (5) | |
C74 | 0.1238 (2) | 0.4814 (2) | 0.8702 (2) | 0.0405 (7) | |
C75 | 0.1453 (2) | 0.5542 (2) | 0.7998 (2) | 0.0383 (7) | |
C76 | 0.2224 (2) | 0.53564 (18) | 0.7242 (2) | 0.0296 (6) | |
C7A | 0.4801 (2) | 0.38918 (16) | 0.68073 (18) | 0.0226 (5) | |
C8 | 0.5537 (2) | 0.38331 (16) | 0.77909 (18) | 0.0242 (5) | |
C81 | 0.5256 (2) | 0.40234 (18) | 0.88976 (18) | 0.0303 (6) | |
N9 | 0.66326 (17) | 0.35376 (14) | 0.76365 (15) | 0.0261 (5) | |
N10 | 0.66424 (16) | 0.33897 (14) | 0.65594 (15) | 0.0247 (5) | |
C101 | 0.7709 (2) | 0.30740 (16) | 0.61566 (19) | 0.0252 (6) | |
C102 | 0.8805 (2) | 0.32605 (17) | 0.67353 (19) | 0.0276 (6) | |
C103 | 0.9843 (2) | 0.29278 (18) | 0.6351 (2) | 0.0321 (6) | |
C104 | 0.9811 (2) | 0.24307 (19) | 0.5400 (2) | 0.0343 (6) | |
C105 | 0.8717 (2) | 0.22735 (19) | 0.4826 (2) | 0.0339 (6) | |
C106 | 0.7663 (2) | 0.25830 (18) | 0.51979 (18) | 0.0289 (6) | |
C10A | 0.5543 (2) | 0.36121 (16) | 0.60378 (18) | 0.0216 (5) | |
N11 | 0.52538 (17) | 0.35726 (14) | 0.49931 (15) | 0.0241 (5) | |
C11A | 0.4128 (2) | 0.38402 (16) | 0.46696 (18) | 0.0223 (5) | |
C11B | 0.3784 (2) | 0.38026 (16) | 0.35164 (18) | 0.0240 (5) | |
H1 | 0.5466 | 0.3550 | 0.3085 | 0.033* | |
H2 | 0.4935 | 0.3450 | 0.1272 | 0.037* | |
H3 | 0.2928 | 0.3666 | 0.0593 | 0.042* | |
H4 | 0.1484 | 0.3956 | 0.1738 | 0.040* | |
H5A | 0.1373 | 0.3307 | 0.4023 | 0.043* | |
H5B | 0.0942 | 0.4330 | 0.3513 | 0.043* | |
H6A | 0.2099 | 0.5194 | 0.4755 | 0.035* | |
H6B | 0.1476 | 0.4371 | 0.5404 | 0.035* | |
H72 | 0.2867 | 0.3147 | 0.7975 | 0.033* | |
H74 | 0.0702 | 0.4951 | 0.9216 | 0.049* | |
H75 | 0.1076 | 0.6160 | 0.8032 | 0.046* | |
H76 | 0.2382 | 0.5842 | 0.6740 | 0.036* | |
H81A | 0.4866 | 0.3449 | 0.9168 | 0.045* | |
H81B | 0.4718 | 0.4586 | 0.8904 | 0.045* | |
H81C | 0.5998 | 0.4160 | 0.9347 | 0.045* | |
H102 | 0.8840 | 0.3611 | 0.7384 | 0.033* | |
H103 | 1.0592 | 0.3043 | 0.6748 | 0.039* | |
H104 | 1.0528 | 0.2202 | 0.5146 | 0.041* | |
H105 | 0.8687 | 0.1947 | 0.4164 | 0.041* | |
H106 | 0.6916 | 0.2460 | 0.4801 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0323 (14) | 0.0244 (13) | 0.0262 (15) | −0.0001 (11) | 0.0002 (12) | 0.0001 (11) |
C2 | 0.0409 (16) | 0.0278 (14) | 0.0248 (15) | 0.0022 (12) | 0.0035 (12) | −0.0004 (11) |
C3 | 0.0462 (17) | 0.0349 (15) | 0.0219 (14) | 0.0005 (13) | −0.0040 (13) | 0.0033 (12) |
C4 | 0.0343 (15) | 0.0346 (15) | 0.0283 (15) | −0.0016 (12) | −0.0071 (12) | 0.0019 (12) |
C4A | 0.0330 (14) | 0.0252 (13) | 0.0262 (15) | −0.0027 (11) | −0.0020 (12) | 0.0036 (11) |
C5 | 0.0315 (14) | 0.0460 (16) | 0.0294 (15) | 0.0003 (13) | −0.0034 (12) | 0.0062 (13) |
C6 | 0.0284 (14) | 0.0317 (14) | 0.0272 (15) | 0.0029 (11) | 0.0015 (11) | 0.0065 (11) |
C6A | 0.0245 (13) | 0.0201 (12) | 0.0242 (14) | −0.0011 (10) | 0.0016 (11) | 0.0017 (10) |
C7 | 0.0283 (13) | 0.0219 (12) | 0.0242 (14) | 0.0018 (10) | 0.0013 (11) | 0.0020 (10) |
C71 | 0.0212 (12) | 0.0241 (13) | 0.0232 (14) | −0.0011 (10) | −0.0014 (10) | −0.0015 (10) |
C72 | 0.0279 (13) | 0.0287 (14) | 0.0260 (14) | 0.0002 (11) | 0.0009 (11) | −0.0008 (11) |
N73 | 0.0339 (12) | 0.0476 (14) | 0.0256 (13) | −0.0063 (11) | 0.0061 (10) | 0.0001 (11) |
C74 | 0.0332 (16) | 0.0570 (19) | 0.0329 (17) | 0.0018 (14) | 0.0114 (13) | −0.0106 (14) |
C75 | 0.0321 (15) | 0.0396 (16) | 0.0432 (18) | 0.0078 (13) | 0.0041 (13) | −0.0083 (14) |
C76 | 0.0279 (13) | 0.0288 (14) | 0.0312 (15) | −0.0004 (11) | −0.0012 (11) | 0.0006 (11) |
C7A | 0.0284 (13) | 0.0196 (12) | 0.0192 (13) | −0.0005 (10) | −0.0005 (10) | 0.0007 (10) |
C8 | 0.0286 (13) | 0.0214 (12) | 0.0221 (13) | −0.0006 (11) | 0.0004 (11) | 0.0018 (10) |
C81 | 0.0338 (14) | 0.0334 (14) | 0.0231 (14) | 0.0028 (12) | 0.0002 (11) | 0.0001 (11) |
N9 | 0.0308 (12) | 0.0290 (11) | 0.0179 (11) | 0.0009 (9) | 0.0000 (9) | −0.0010 (9) |
N10 | 0.0243 (11) | 0.0303 (11) | 0.0187 (11) | 0.0022 (9) | −0.0016 (9) | 0.0003 (9) |
C101 | 0.0260 (13) | 0.0253 (13) | 0.0241 (14) | −0.0009 (10) | 0.0015 (11) | 0.0046 (11) |
C102 | 0.0285 (14) | 0.0286 (13) | 0.0247 (14) | −0.0032 (11) | −0.0028 (11) | 0.0024 (11) |
C103 | 0.0246 (14) | 0.0394 (15) | 0.0312 (16) | −0.0059 (12) | −0.0033 (12) | 0.0082 (12) |
C104 | 0.0283 (15) | 0.0446 (16) | 0.0310 (16) | 0.0020 (13) | 0.0077 (12) | 0.0111 (13) |
C105 | 0.0345 (15) | 0.0459 (16) | 0.0217 (14) | 0.0031 (13) | 0.0040 (12) | 0.0008 (12) |
C106 | 0.0282 (14) | 0.0362 (15) | 0.0214 (14) | 0.0007 (12) | −0.0023 (11) | −0.0017 (11) |
C10A | 0.0221 (12) | 0.0209 (12) | 0.0210 (13) | −0.0020 (10) | −0.0014 (10) | 0.0001 (10) |
N11 | 0.0247 (11) | 0.0268 (11) | 0.0201 (11) | 0.0001 (9) | −0.0015 (9) | 0.0004 (9) |
C11A | 0.0249 (13) | 0.0190 (12) | 0.0221 (13) | −0.0029 (10) | −0.0020 (10) | 0.0020 (10) |
C11B | 0.0291 (13) | 0.0194 (12) | 0.0224 (13) | −0.0028 (10) | −0.0028 (11) | 0.0020 (10) |
C1—C2 | 1.379 (3) | C75—C76 | 1.379 (3) |
C1—C11B | 1.405 (3) | C75—H75 | 0.95 |
C1—H1 | 0.95 | C76—H76 | 0.95 |
C2—C3 | 1.394 (4) | C7A—C10A | 1.399 (3) |
C2—H2 | 0.95 | C7A—C8 | 1.429 (3) |
C3—C4 | 1.376 (3) | C8—N9 | 1.328 (3) |
C3—H3 | 0.95 | C8—C81 | 1.493 (3) |
C4—C4A | 1.395 (3) | C81—H81A | 0.98 |
C4—H4 | 0.95 | C81—H81B | 0.98 |
C4A—C11B | 1.398 (3) | C81—H81C | 0.98 |
C4A—C5 | 1.499 (3) | N9—N10 | 1.383 (2) |
C5—C6 | 1.512 (3) | N10—C10A | 1.375 (3) |
C5—H5A | 0.99 | N10—C101 | 1.416 (3) |
C5—H5B | 0.99 | C101—C106 | 1.387 (3) |
C6—C6A | 1.510 (3) | C101—C102 | 1.393 (3) |
C6—H6A | 0.99 | C102—C103 | 1.385 (3) |
C6—H6B | 0.99 | C102—H102 | 0.95 |
C6A—C7 | 1.393 (3) | C103—C104 | 1.384 (3) |
C6A—C11A | 1.424 (3) | C103—H103 | 0.95 |
C7—C7A | 1.408 (3) | C104—C105 | 1.381 (3) |
C7—C71 | 1.488 (3) | C104—H104 | 0.95 |
C71—C72 | 1.387 (3) | C105—C106 | 1.383 (3) |
C71—C76 | 1.392 (3) | C105—H105 | 0.95 |
C72—N73 | 1.339 (3) | C106—H106 | 0.95 |
C72—H72 | 0.95 | C10A—N11 | 1.334 (3) |
N73—C74 | 1.332 (3) | N11—C11A | 1.341 (3) |
C74—C75 | 1.377 (4) | C11A—C11B | 1.477 (3) |
C74—H74 | 0.95 | ||
C2—C1—C11B | 121.0 (2) | C75—C76—H76 | 120.6 |
C2—C1—H1 | 119.5 | C71—C76—H76 | 120.6 |
C11B—C1—H1 | 119.5 | C10A—C7A—C7 | 117.3 (2) |
C1—C2—C3 | 119.8 (2) | C10A—C7A—C8 | 105.15 (19) |
C1—C2—H2 | 120.1 | C7—C7A—C8 | 137.5 (2) |
C3—C2—H2 | 120.1 | N9—C8—C7A | 110.6 (2) |
C4—C3—C2 | 119.5 (2) | N9—C8—C81 | 118.6 (2) |
C4—C3—H3 | 120.2 | C7A—C8—C81 | 130.8 (2) |
C2—C3—H3 | 120.2 | C8—C81—H81A | 109.5 |
C3—C4—C4A | 121.6 (2) | C8—C81—H81B | 109.5 |
C3—C4—H4 | 119.2 | H81A—C81—H81B | 109.5 |
C4A—C4—H4 | 119.2 | C8—C81—H81C | 109.5 |
C4—C4A—C11B | 119.0 (2) | H81A—C81—H81C | 109.5 |
C4—C4A—C5 | 121.5 (2) | H81B—C81—H81C | 109.5 |
C11B—C4A—C5 | 119.3 (2) | C8—N9—N10 | 106.83 (18) |
C4A—C5—C6 | 113.0 (2) | C10A—N10—N9 | 110.36 (18) |
C4A—C5—H5A | 109.0 | C10A—N10—C101 | 130.14 (19) |
C6—C5—H5A | 109.0 | N9—N10—C101 | 119.49 (18) |
C4A—C5—H5B | 109.0 | C106—C101—C102 | 120.3 (2) |
C6—C5—H5B | 109.0 | C106—C101—N10 | 120.4 (2) |
H5A—C5—H5B | 107.8 | C102—C101—N10 | 119.2 (2) |
C6A—C6—C5 | 113.7 (2) | C103—C102—C101 | 119.0 (2) |
C6A—C6—H6A | 108.8 | C103—C102—H102 | 120.5 |
C5—C6—H6A | 108.8 | C101—C102—H102 | 120.5 |
C6A—C6—H6B | 108.8 | C104—C103—C102 | 121.3 (2) |
C5—C6—H6B | 108.8 | C104—C103—H103 | 119.3 |
H6A—C6—H6B | 107.7 | C102—C103—H103 | 119.3 |
C7—C6A—C11A | 119.3 (2) | C105—C104—C103 | 118.8 (2) |
C7—C6A—C6 | 122.6 (2) | C105—C104—H104 | 120.6 |
C11A—C6A—C6 | 118.1 (2) | C103—C104—H104 | 120.6 |
C6A—C7—C7A | 117.7 (2) | C104—C105—C106 | 121.2 (2) |
C6A—C7—C71 | 122.0 (2) | C104—C105—H105 | 119.4 |
C7A—C7—C71 | 120.2 (2) | C106—C105—H105 | 119.4 |
C72—C71—C76 | 117.6 (2) | C105—C106—C101 | 119.4 (2) |
C72—C71—C7 | 119.4 (2) | C105—C106—H106 | 120.3 |
C76—C71—C7 | 123.0 (2) | C101—C106—H106 | 120.3 |
N73—C72—C71 | 124.4 (2) | N11—C10A—N10 | 125.9 (2) |
N73—C72—H72 | 117.8 | N11—C10A—C7A | 127.0 (2) |
C71—C72—H72 | 117.8 | N10—C10A—C7A | 107.05 (19) |
C74—N73—C72 | 116.2 (2) | C10A—N11—C11A | 114.93 (19) |
N73—C74—C75 | 124.3 (2) | N11—C11A—C6A | 123.8 (2) |
N73—C74—H74 | 117.9 | N11—C11A—C11B | 116.05 (19) |
C75—C74—H74 | 117.9 | C6A—C11A—C11B | 120.1 (2) |
C74—C75—C76 | 118.7 (2) | C4A—C11B—C1 | 119.1 (2) |
C74—C75—H75 | 120.6 | C4A—C11B—C11A | 120.5 (2) |
C76—C75—H75 | 120.6 | C1—C11B—C11A | 120.3 (2) |
C75—C76—C71 | 118.8 (2) | ||
C11B—C1—C2—C3 | 0.5 (4) | C10A—N10—C101—C106 | −25.7 (4) |
C1—C2—C3—C4 | −0.6 (4) | N9—N10—C101—C106 | 156.0 (2) |
C2—C3—C4—C4A | −0.5 (4) | C10A—N10—C101—C102 | 154.5 (2) |
C3—C4—C4A—C11B | 1.7 (4) | N9—N10—C101—C102 | −23.9 (3) |
C3—C4—C4A—C5 | −172.6 (2) | C106—C101—C102—C103 | −1.5 (3) |
C4—C4A—C5—C6 | −152.2 (2) | N10—C101—C102—C103 | 178.3 (2) |
C11B—C4A—C5—C6 | 33.5 (3) | C101—C102—C103—C104 | 1.1 (4) |
C4A—C5—C6—C6A | −45.8 (3) | C102—C103—C104—C105 | 0.4 (4) |
C5—C6—C6A—C7 | −151.7 (2) | C103—C104—C105—C106 | −1.5 (4) |
C5—C6—C6A—C11A | 31.8 (3) | C104—C105—C106—C101 | 1.1 (4) |
C11A—C6A—C7—C7A | −0.1 (3) | C102—C101—C106—C105 | 0.5 (4) |
C6—C6A—C7—C7A | −176.6 (2) | N10—C101—C106—C105 | −179.4 (2) |
C11A—C6A—C7—C71 | −177.3 (2) | N9—N10—C10A—N11 | 178.3 (2) |
C6—C6A—C7—C71 | 6.3 (3) | C101—N10—C10A—N11 | −0.2 (4) |
C6A—C7—C71—C72 | 117.8 (3) | N9—N10—C10A—C7A | −1.2 (2) |
C7A—C7—C71—C72 | −59.4 (3) | C101—N10—C10A—C7A | −179.7 (2) |
C6A—C7—C71—C76 | −62.5 (3) | C7—C7A—C10A—N11 | −0.7 (3) |
C7A—C7—C71—C76 | 120.4 (3) | C8—C7A—C10A—N11 | −178.6 (2) |
C76—C71—C72—N73 | 0.5 (4) | C7—C7A—C10A—N10 | 178.8 (2) |
C7—C71—C72—N73 | −179.7 (2) | C8—C7A—C10A—N10 | 0.9 (2) |
C71—C72—N73—C74 | −1.0 (4) | N10—C10A—N11—C11A | −178.9 (2) |
C72—N73—C74—C75 | 0.6 (4) | C7A—C10A—N11—C11A | 0.5 (3) |
N73—C74—C75—C76 | 0.3 (4) | C10A—N11—C11A—C6A | 0.0 (3) |
C74—C75—C76—C71 | −0.7 (4) | C10A—N11—C11A—C11B | −179.96 (19) |
C72—C71—C76—C75 | 0.4 (3) | C7—C6A—C11A—N11 | −0.2 (3) |
C7—C71—C76—C75 | −179.4 (2) | C6—C6A—C11A—N11 | 176.5 (2) |
C6A—C7—C7A—C10A | 0.4 (3) | C7—C6A—C11A—C11B | 179.8 (2) |
C71—C7—C7A—C10A | 177.7 (2) | C6—C6A—C11A—C11B | −3.6 (3) |
C6A—C7—C7A—C8 | 177.4 (2) | C4—C4A—C11B—C1 | −1.7 (3) |
C71—C7—C7A—C8 | −5.3 (4) | C5—C4A—C11B—C1 | 172.7 (2) |
C10A—C7A—C8—N9 | −0.3 (3) | C4—C4A—C11B—C11A | −179.8 (2) |
C7—C7A—C8—N9 | −177.6 (3) | C5—C4A—C11B—C11A | −5.3 (3) |
C10A—C7A—C8—C81 | −178.8 (2) | C2—C1—C11B—C4A | 0.6 (3) |
C7—C7A—C8—C81 | 3.9 (5) | C2—C1—C11B—C11A | 178.7 (2) |
C7A—C8—N9—N10 | −0.4 (2) | N11—C11A—C11B—C4A | 169.4 (2) |
C81—C8—N9—N10 | 178.32 (19) | C6A—C11A—C11B—C4A | −10.6 (3) |
C8—N9—N10—C10A | 1.0 (2) | N11—C11A—C11B—C1 | −8.7 (3) |
C8—N9—N10—C101 | 179.64 (19) | C6A—C11A—C11B—C1 | 171.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···Cg1i | 0.95 | 2.79 | 3.706 (3) | 163 |
C75—H75···Cg2ii | 0.95 | 2.66 | 3.431 (3) | 139 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2. |
C28H23N3 | Z = 4 |
Mr = 401.49 | F(000) = 848 |
Triclinic, P1 | Dx = 1.265 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1334 (3) Å | Cell parameters from 9647 reflections |
b = 11.4672 (2) Å | θ = 3.1–27.5° |
c = 17.6270 (4) Å | µ = 0.08 mm−1 |
α = 97.858 (2)° | T = 118 K |
β = 106.135 (3)° | Block, colourless |
γ = 97.496 (2)° | 0.20 × 0.18 × 0.12 mm |
V = 2107.66 (9) Å3 |
Bruker-Nonius KappaCCD diffractometer | 9647 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 7878 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ & ω scans | h = −14→14 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −14→14 |
Tmin = 0.982, Tmax = 0.991 | l = −22→22 |
40500 measured reflections |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0391P)2 + 0.8878P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
9647 reflections | Δρmax = 0.27 e Å−3 |
564 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0084 (11) |
C28H23N3 | γ = 97.496 (2)° |
Mr = 401.49 | V = 2107.66 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.1334 (3) Å | Mo Kα radiation |
b = 11.4672 (2) Å | µ = 0.08 mm−1 |
c = 17.6270 (4) Å | T = 118 K |
α = 97.858 (2)° | 0.20 × 0.18 × 0.12 mm |
β = 106.135 (3)° |
Bruker-Nonius KappaCCD diffractometer | 9647 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 7878 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.991 | Rint = 0.048 |
40500 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.27 e Å−3 |
9647 reflections | Δρmin = −0.25 e Å−3 |
564 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.76702 (13) | 0.13359 (12) | 0.70638 (8) | 0.0231 (3) | |
C12 | 0.84744 (13) | 0.06640 (13) | 0.74874 (8) | 0.0270 (3) | |
C13 | 0.79830 (14) | −0.04070 (13) | 0.76593 (8) | 0.0291 (3) | |
C14 | 0.66844 (14) | −0.08129 (12) | 0.73877 (8) | 0.0274 (3) | |
C14A | 0.58640 (13) | −0.01522 (12) | 0.69584 (8) | 0.0233 (3) | |
C15 | 0.44612 (13) | −0.06230 (12) | 0.66176 (8) | 0.0260 (3) | |
C16 | 0.40133 (13) | −0.03677 (12) | 0.57661 (8) | 0.0250 (3) | |
C16A | 0.42946 (12) | 0.09592 (11) | 0.57860 (7) | 0.0206 (3) | |
N17 | 0.33956 (10) | 0.14059 (10) | 0.53005 (6) | 0.0217 (2) | |
C17A | 0.36189 (12) | 0.25987 (12) | 0.53819 (8) | 0.0215 (3) | |
N18 | 0.27858 (10) | 0.32785 (10) | 0.50155 (7) | 0.0232 (2) | |
C181 | 0.15148 (12) | 0.29245 (12) | 0.45074 (8) | 0.0233 (3) | |
C182 | 0.06670 (14) | 0.37166 (13) | 0.44997 (8) | 0.0288 (3) | |
C183 | −0.05767 (14) | 0.33700 (14) | 0.40046 (9) | 0.0324 (3) | |
C184 | −0.09774 (14) | 0.22439 (14) | 0.35293 (8) | 0.0312 (3) | |
C185 | −0.01271 (14) | 0.14644 (14) | 0.35424 (8) | 0.0313 (3) | |
C186 | 0.11247 (14) | 0.17981 (13) | 0.40228 (8) | 0.0277 (3) | |
N19 | 0.32713 (11) | 0.44784 (10) | 0.53033 (7) | 0.0252 (3) | |
C110 | 0.44023 (13) | 0.45582 (12) | 0.58249 (8) | 0.0232 (3) | |
C111 | 0.51441 (14) | 0.57777 (12) | 0.62257 (9) | 0.0281 (3) | |
C11A | 0.46874 (12) | 0.33862 (12) | 0.59048 (8) | 0.0214 (3) | |
C120 | 0.56542 (12) | 0.28977 (12) | 0.63979 (7) | 0.0202 (3) | |
C121 | 0.67737 (12) | 0.37387 (11) | 0.69659 (8) | 0.0211 (3) | |
C122 | 0.70603 (13) | 0.37927 (12) | 0.77959 (8) | 0.0234 (3) | |
C123 | 0.80874 (13) | 0.45979 (13) | 0.83192 (8) | 0.0272 (3) | |
C124 | 0.88571 (13) | 0.53841 (13) | 0.80359 (9) | 0.0283 (3) | |
C127 | 0.99923 (15) | 0.62415 (15) | 0.86080 (10) | 0.0416 (4) | |
C125 | 0.85528 (13) | 0.53406 (12) | 0.72125 (9) | 0.0283 (3) | |
C126 | 0.75319 (13) | 0.45290 (12) | 0.66827 (8) | 0.0249 (3) | |
C12A | 0.54504 (12) | 0.16477 (11) | 0.63347 (7) | 0.0200 (3) | |
C12B | 0.63528 (12) | 0.09562 (11) | 0.68004 (7) | 0.0210 (3) | |
C21 | 0.26100 (13) | 0.10371 (12) | 0.85434 (8) | 0.0235 (3) | |
C22 | 0.21280 (14) | −0.01670 (12) | 0.84542 (8) | 0.0268 (3) | |
C23 | 0.29433 (14) | −0.09863 (12) | 0.85298 (8) | 0.0291 (3) | |
C24 | 0.42420 (14) | −0.06002 (12) | 0.87372 (8) | 0.0284 (3) | |
C24A | 0.47414 (13) | 0.06119 (12) | 0.88507 (8) | 0.0238 (3) | |
C25 | 0.61529 (14) | 0.10783 (12) | 0.91573 (9) | 0.0291 (3) | |
C26 | 0.63935 (13) | 0.22366 (12) | 0.97612 (8) | 0.0272 (3) | |
C26A | 0.56894 (12) | 0.31343 (11) | 0.93711 (7) | 0.0204 (3) | |
N27 | 0.62967 (10) | 0.42643 (9) | 0.95639 (6) | 0.0203 (2) | |
C27A | 0.56717 (12) | 0.50140 (11) | 0.91516 (7) | 0.0191 (3) | |
N28 | 0.61281 (10) | 0.61981 (9) | 0.91951 (6) | 0.0216 (2) | |
C281 | 0.73369 (13) | 0.68915 (11) | 0.96228 (8) | 0.0225 (3) | |
C282 | 0.77068 (15) | 0.79603 (13) | 0.93996 (9) | 0.0345 (4) | |
C283 | 0.89001 (16) | 0.86292 (14) | 0.97970 (10) | 0.0428 (4) | |
C284 | 0.97328 (15) | 0.82448 (14) | 1.04163 (9) | 0.0346 (4) | |
C285 | 0.93559 (14) | 0.71839 (12) | 1.06406 (8) | 0.0274 (3) | |
C286 | 0.81590 (13) | 0.65044 (12) | 1.02510 (8) | 0.0244 (3) | |
N29 | 0.53025 (11) | 0.66579 (10) | 0.86193 (7) | 0.0239 (2) | |
C210 | 0.43371 (12) | 0.57910 (11) | 0.82319 (8) | 0.0214 (3) | |
C211 | 0.33001 (13) | 0.60331 (12) | 0.75570 (8) | 0.0265 (3) | |
C21A | 0.45005 (12) | 0.47110 (11) | 0.85453 (7) | 0.0190 (3) | |
C220 | 0.38661 (12) | 0.35155 (11) | 0.83545 (7) | 0.0188 (3) | |
C221 | 0.26855 (12) | 0.31116 (11) | 0.76664 (7) | 0.0198 (3) | |
C222 | 0.26628 (13) | 0.22212 (12) | 0.70368 (8) | 0.0237 (3) | |
C223 | 0.15693 (13) | 0.18094 (13) | 0.63957 (8) | 0.0271 (3) | |
C224 | 0.04690 (13) | 0.22813 (13) | 0.63584 (8) | 0.0271 (3) | |
C227 | −0.07194 (14) | 0.18075 (16) | 0.56634 (9) | 0.0376 (4) | |
C225 | 0.05008 (13) | 0.31820 (13) | 0.69796 (8) | 0.0262 (3) | |
C226 | 0.15915 (12) | 0.35912 (12) | 0.76279 (8) | 0.0228 (3) | |
C22A | 0.44649 (12) | 0.27213 (11) | 0.88046 (7) | 0.0199 (3) | |
C22B | 0.39140 (13) | 0.14378 (11) | 0.87194 (7) | 0.0214 (3) | |
H11 | 0.8020 | 0.2069 | 0.6950 | 0.028* | |
H12 | 0.9366 | 0.0939 | 0.7661 | 0.032* | |
H13 | 0.8532 | −0.0859 | 0.7961 | 0.035* | |
H14 | 0.6348 | −0.1555 | 0.7496 | 0.033* | |
H15A | 0.4000 | −0.0227 | 0.6955 | 0.031* | |
H15B | 0.4289 | −0.1495 | 0.6608 | 0.031* | |
H16A | 0.4455 | −0.0788 | 0.5426 | 0.030* | |
H16B | 0.3089 | −0.0665 | 0.5532 | 0.030* | |
H182 | 0.0937 | 0.4487 | 0.4830 | 0.035* | |
H183 | −0.1157 | 0.3910 | 0.3992 | 0.039* | |
H184 | −0.1832 | 0.2008 | 0.3196 | 0.037* | |
H185 | −0.0404 | 0.0690 | 0.3218 | 0.038* | |
H186 | 0.1709 | 0.1264 | 0.4021 | 0.033* | |
H11A | 0.4600 | 0.6377 | 0.6107 | 0.042* | |
H11B | 0.5875 | 0.5943 | 0.6025 | 0.042* | |
H11C | 0.5443 | 0.5812 | 0.6808 | 0.042* | |
H122 | 0.6546 | 0.3272 | 0.8002 | 0.028* | |
H123 | 0.8273 | 0.4617 | 0.8881 | 0.033* | |
H12A | 1.0636 | 0.5791 | 0.8859 | 0.062* | 0.50 |
H12B | 0.9728 | 0.6704 | 0.9024 | 0.062* | 0.50 |
H12C | 1.0350 | 0.6787 | 0.8312 | 0.062* | 0.50 |
H12D | 0.9840 | 0.7064 | 0.8605 | 0.062* | 0.50 |
H12E | 1.0748 | 0.6150 | 0.8439 | 0.062* | 0.50 |
H12F | 1.0127 | 0.6068 | 0.9152 | 0.062* | 0.50 |
H125 | 0.9053 | 0.5877 | 0.7007 | 0.034* | |
H126 | 0.7348 | 0.4512 | 0.6121 | 0.030* | |
H21 | 0.2047 | 0.1597 | 0.8484 | 0.028* | |
H22 | 0.1241 | −0.0429 | 0.8342 | 0.032* | |
H23 | 0.2611 | −0.1817 | 0.8439 | 0.035* | |
H24 | 0.4798 | −0.1166 | 0.8803 | 0.034* | |
H25A | 0.6478 | 0.1231 | 0.8705 | 0.035* | |
H25B | 0.6600 | 0.0479 | 0.9419 | 0.035* | |
H26A | 0.6107 | 0.2071 | 1.0226 | 0.033* | |
H26B | 0.7315 | 0.2564 | 0.9960 | 0.033* | |
H282 | 0.7144 | 0.8233 | 0.8976 | 0.041* | |
H283 | 0.9153 | 0.9362 | 0.9643 | 0.051* | |
H284 | 1.0553 | 0.8706 | 1.0683 | 0.041* | |
H285 | 0.9920 | 0.6916 | 1.1066 | 0.033* | |
H286 | 0.7903 | 0.5779 | 1.0412 | 0.029* | |
H21A | 0.3554 | 0.6818 | 0.7432 | 0.040* | |
H21B | 0.2522 | 0.6026 | 0.7715 | 0.040* | |
H21C | 0.3145 | 0.5414 | 0.7082 | 0.040* | |
H222 | 0.3406 | 0.1892 | 0.7047 | 0.028* | |
H223 | 0.1571 | 0.1196 | 0.5975 | 0.033* | |
H27A | −0.1158 | 0.1066 | 0.5754 | 0.056* | |
H27B | −0.0491 | 0.1647 | 0.5166 | 0.056* | |
H27C | −0.1281 | 0.2402 | 0.5619 | 0.056* | |
H225 | −0.0236 | 0.3525 | 0.6961 | 0.031* | |
H226 | 0.1588 | 0.4204 | 0.8048 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0225 (7) | 0.0249 (7) | 0.0211 (6) | 0.0031 (5) | 0.0065 (5) | 0.0022 (5) |
C12 | 0.0205 (7) | 0.0331 (7) | 0.0245 (7) | 0.0070 (6) | 0.0029 (5) | 0.0014 (6) |
C13 | 0.0292 (8) | 0.0315 (7) | 0.0245 (7) | 0.0113 (6) | 0.0019 (6) | 0.0050 (6) |
C14 | 0.0315 (8) | 0.0237 (7) | 0.0250 (7) | 0.0049 (6) | 0.0057 (6) | 0.0043 (5) |
C14A | 0.0235 (7) | 0.0245 (7) | 0.0200 (6) | 0.0038 (5) | 0.0049 (5) | 0.0015 (5) |
C15 | 0.0251 (7) | 0.0219 (7) | 0.0295 (7) | 0.0022 (5) | 0.0066 (6) | 0.0049 (5) |
C16 | 0.0220 (7) | 0.0234 (7) | 0.0252 (7) | 0.0022 (5) | 0.0024 (5) | 0.0008 (5) |
C16A | 0.0190 (6) | 0.0242 (6) | 0.0180 (6) | 0.0039 (5) | 0.0058 (5) | 0.0011 (5) |
N17 | 0.0211 (6) | 0.0244 (6) | 0.0183 (5) | 0.0041 (4) | 0.0052 (4) | 0.0016 (4) |
C17A | 0.0210 (6) | 0.0259 (7) | 0.0179 (6) | 0.0051 (5) | 0.0061 (5) | 0.0041 (5) |
N18 | 0.0214 (6) | 0.0237 (6) | 0.0221 (6) | 0.0044 (4) | 0.0025 (5) | 0.0043 (4) |
C181 | 0.0207 (7) | 0.0303 (7) | 0.0179 (6) | 0.0045 (5) | 0.0034 (5) | 0.0062 (5) |
C182 | 0.0277 (7) | 0.0317 (8) | 0.0241 (7) | 0.0074 (6) | 0.0036 (6) | 0.0020 (6) |
C183 | 0.0263 (8) | 0.0414 (9) | 0.0277 (7) | 0.0133 (6) | 0.0025 (6) | 0.0056 (6) |
C184 | 0.0234 (7) | 0.0424 (9) | 0.0228 (7) | 0.0049 (6) | −0.0005 (6) | 0.0057 (6) |
C185 | 0.0316 (8) | 0.0341 (8) | 0.0212 (7) | 0.0044 (6) | −0.0005 (6) | 0.0007 (6) |
C186 | 0.0268 (7) | 0.0322 (7) | 0.0221 (7) | 0.0091 (6) | 0.0030 (6) | 0.0034 (6) |
N19 | 0.0247 (6) | 0.0244 (6) | 0.0253 (6) | 0.0044 (5) | 0.0057 (5) | 0.0044 (5) |
C110 | 0.0229 (7) | 0.0258 (7) | 0.0212 (6) | 0.0042 (5) | 0.0067 (5) | 0.0051 (5) |
C111 | 0.0270 (7) | 0.0247 (7) | 0.0306 (7) | 0.0034 (6) | 0.0068 (6) | 0.0036 (6) |
C11A | 0.0204 (6) | 0.0243 (6) | 0.0191 (6) | 0.0027 (5) | 0.0060 (5) | 0.0031 (5) |
C120 | 0.0186 (6) | 0.0253 (6) | 0.0173 (6) | 0.0030 (5) | 0.0074 (5) | 0.0028 (5) |
C121 | 0.0189 (6) | 0.0213 (6) | 0.0222 (6) | 0.0043 (5) | 0.0048 (5) | 0.0028 (5) |
C122 | 0.0221 (7) | 0.0245 (7) | 0.0230 (7) | 0.0033 (5) | 0.0068 (5) | 0.0026 (5) |
C123 | 0.0247 (7) | 0.0323 (7) | 0.0218 (7) | 0.0053 (6) | 0.0055 (6) | −0.0013 (6) |
C124 | 0.0195 (7) | 0.0282 (7) | 0.0324 (8) | 0.0008 (5) | 0.0062 (6) | −0.0040 (6) |
C127 | 0.0286 (8) | 0.0429 (9) | 0.0419 (9) | −0.0074 (7) | 0.0072 (7) | −0.0107 (7) |
C125 | 0.0234 (7) | 0.0259 (7) | 0.0354 (8) | 0.0007 (6) | 0.0104 (6) | 0.0052 (6) |
C126 | 0.0233 (7) | 0.0266 (7) | 0.0247 (7) | 0.0044 (5) | 0.0066 (5) | 0.0064 (5) |
C12A | 0.0184 (6) | 0.0243 (6) | 0.0178 (6) | 0.0036 (5) | 0.0067 (5) | 0.0032 (5) |
C12B | 0.0215 (7) | 0.0238 (6) | 0.0167 (6) | 0.0046 (5) | 0.0049 (5) | 0.0010 (5) |
C21 | 0.0256 (7) | 0.0225 (6) | 0.0205 (6) | 0.0027 (5) | 0.0048 (5) | 0.0035 (5) |
C22 | 0.0279 (7) | 0.0257 (7) | 0.0215 (7) | −0.0033 (6) | 0.0028 (6) | 0.0042 (5) |
C23 | 0.0400 (8) | 0.0184 (6) | 0.0222 (7) | −0.0029 (6) | 0.0017 (6) | 0.0052 (5) |
C24 | 0.0376 (8) | 0.0201 (7) | 0.0248 (7) | 0.0060 (6) | 0.0038 (6) | 0.0060 (5) |
C24A | 0.0290 (7) | 0.0209 (6) | 0.0202 (6) | 0.0046 (5) | 0.0042 (5) | 0.0059 (5) |
C25 | 0.0278 (8) | 0.0219 (7) | 0.0358 (8) | 0.0079 (6) | 0.0030 (6) | 0.0097 (6) |
C26 | 0.0250 (7) | 0.0243 (7) | 0.0273 (7) | 0.0023 (5) | −0.0014 (6) | 0.0088 (6) |
C26A | 0.0217 (7) | 0.0210 (6) | 0.0178 (6) | 0.0032 (5) | 0.0046 (5) | 0.0048 (5) |
N27 | 0.0210 (6) | 0.0203 (5) | 0.0186 (5) | 0.0033 (4) | 0.0039 (4) | 0.0044 (4) |
C27A | 0.0209 (6) | 0.0183 (6) | 0.0176 (6) | 0.0034 (5) | 0.0055 (5) | 0.0020 (5) |
N28 | 0.0217 (6) | 0.0170 (5) | 0.0221 (5) | 0.0031 (4) | 0.0007 (4) | 0.0029 (4) |
C281 | 0.0229 (7) | 0.0190 (6) | 0.0211 (6) | 0.0014 (5) | 0.0028 (5) | −0.0009 (5) |
C282 | 0.0335 (8) | 0.0261 (7) | 0.0321 (8) | −0.0038 (6) | −0.0064 (6) | 0.0087 (6) |
C283 | 0.0415 (9) | 0.0292 (8) | 0.0423 (9) | −0.0125 (7) | −0.0066 (7) | 0.0129 (7) |
C284 | 0.0300 (8) | 0.0320 (8) | 0.0298 (8) | −0.0078 (6) | −0.0022 (6) | 0.0020 (6) |
C285 | 0.0268 (7) | 0.0269 (7) | 0.0229 (7) | 0.0033 (6) | 0.0010 (6) | 0.0012 (5) |
C286 | 0.0271 (7) | 0.0208 (6) | 0.0219 (6) | 0.0020 (5) | 0.0039 (5) | 0.0019 (5) |
N29 | 0.0227 (6) | 0.0200 (5) | 0.0249 (6) | 0.0044 (4) | −0.0001 (5) | 0.0051 (4) |
C210 | 0.0222 (7) | 0.0192 (6) | 0.0219 (6) | 0.0052 (5) | 0.0050 (5) | 0.0029 (5) |
C211 | 0.0243 (7) | 0.0225 (7) | 0.0287 (7) | 0.0047 (5) | 0.0006 (6) | 0.0069 (5) |
C21A | 0.0191 (6) | 0.0199 (6) | 0.0179 (6) | 0.0046 (5) | 0.0052 (5) | 0.0024 (5) |
C220 | 0.0186 (6) | 0.0204 (6) | 0.0171 (6) | 0.0033 (5) | 0.0060 (5) | 0.0014 (5) |
C221 | 0.0186 (6) | 0.0207 (6) | 0.0194 (6) | 0.0019 (5) | 0.0042 (5) | 0.0059 (5) |
C222 | 0.0213 (7) | 0.0260 (7) | 0.0233 (7) | 0.0033 (5) | 0.0072 (5) | 0.0029 (5) |
C223 | 0.0257 (7) | 0.0328 (7) | 0.0198 (6) | −0.0011 (6) | 0.0073 (6) | −0.0006 (5) |
C224 | 0.0201 (7) | 0.0377 (8) | 0.0206 (7) | −0.0024 (6) | 0.0038 (5) | 0.0082 (6) |
C227 | 0.0232 (8) | 0.0588 (10) | 0.0233 (7) | −0.0041 (7) | 0.0008 (6) | 0.0063 (7) |
C225 | 0.0174 (6) | 0.0309 (7) | 0.0303 (7) | 0.0040 (5) | 0.0053 (6) | 0.0095 (6) |
C226 | 0.0215 (7) | 0.0213 (6) | 0.0246 (7) | 0.0037 (5) | 0.0055 (5) | 0.0041 (5) |
C22A | 0.0209 (6) | 0.0197 (6) | 0.0190 (6) | 0.0034 (5) | 0.0060 (5) | 0.0033 (5) |
C22B | 0.0249 (7) | 0.0198 (6) | 0.0173 (6) | 0.0014 (5) | 0.0036 (5) | 0.0035 (5) |
C11—C12 | 1.3851 (19) | C12A—C12B | 1.4965 (18) |
C11—C12B | 1.3986 (18) | C21—C22 | 1.3855 (18) |
C11—H11 | 0.95 | C21—C22B | 1.3971 (19) |
C12—C13 | 1.385 (2) | C21—H21 | 0.95 |
C12—H12 | 0.95 | C22—C23 | 1.383 (2) |
C13—C14 | 1.384 (2) | C22—H22 | 0.95 |
C13—H13 | 0.95 | C23—C24 | 1.384 (2) |
C14—C14A | 1.3907 (19) | C23—H23 | 0.95 |
C14—H14 | 0.95 | C24—C24A | 1.3934 (18) |
C14A—C12B | 1.4106 (18) | C24—H24 | 0.95 |
C14A—C15 | 1.5038 (19) | C24A—C22B | 1.4029 (19) |
C15—C16 | 1.5263 (19) | C24A—C25 | 1.5090 (19) |
C15—H15A | 0.99 | C25—C26 | 1.527 (2) |
C15—H15B | 0.99 | C25—H25A | 0.99 |
C16—C16A | 1.5065 (18) | C25—H25B | 0.99 |
C16—H16A | 0.99 | C26—C26A | 1.5004 (18) |
C16—H16B | 0.99 | C26—H26A | 0.99 |
C16A—N17 | 1.3320 (17) | C26—H26B | 0.99 |
C16A—C12A | 1.4314 (17) | C26A—N27 | 1.3323 (16) |
N17—C17A | 1.3384 (17) | C26A—C22A | 1.4232 (18) |
C17A—N18 | 1.3705 (17) | N27—C27A | 1.3407 (16) |
C17A—C11A | 1.4011 (18) | C27A—N28 | 1.3703 (16) |
N18—N19 | 1.3804 (15) | C27A—C21A | 1.4033 (17) |
N18—C181 | 1.4197 (17) | N28—N29 | 1.3811 (15) |
C181—C186 | 1.3901 (19) | N28—C281 | 1.4159 (16) |
C181—C182 | 1.3914 (19) | C281—C282 | 1.3845 (19) |
C182—C183 | 1.388 (2) | C281—C286 | 1.3922 (18) |
C182—H182 | 0.95 | C282—C283 | 1.383 (2) |
C183—C184 | 1.384 (2) | C282—H282 | 0.95 |
C183—H183 | 0.95 | C283—C284 | 1.386 (2) |
C184—C185 | 1.382 (2) | C283—H283 | 0.95 |
C184—H184 | 0.95 | C284—C285 | 1.379 (2) |
C185—C186 | 1.386 (2) | C284—H284 | 0.95 |
C185—H185 | 0.95 | C285—C286 | 1.3887 (19) |
C186—H186 | 0.95 | C285—H285 | 0.95 |
N19—C110 | 1.3202 (17) | C286—H286 | 0.95 |
C110—C11A | 1.4370 (19) | N29—C210 | 1.3181 (17) |
C110—C111 | 1.4969 (18) | C210—C21A | 1.4359 (18) |
C111—H11A | 0.98 | C210—C211 | 1.4953 (18) |
C111—H11B | 0.98 | C211—H21A | 0.98 |
C111—H11C | 0.98 | C211—H21B | 0.98 |
C11A—C120 | 1.4137 (18) | C211—H21C | 0.98 |
C120—C12A | 1.4056 (18) | C21A—C220 | 1.4073 (17) |
C120—C121 | 1.4882 (18) | C220—C22A | 1.4019 (18) |
C121—C126 | 1.3934 (18) | C220—C221 | 1.4883 (17) |
C121—C122 | 1.3988 (18) | C221—C226 | 1.3892 (18) |
C122—C123 | 1.3844 (19) | C221—C222 | 1.3937 (18) |
C122—H122 | 0.95 | C222—C223 | 1.3862 (19) |
C123—C124 | 1.398 (2) | C222—H222 | 0.95 |
C123—H123 | 0.95 | C223—C224 | 1.391 (2) |
C124—C125 | 1.388 (2) | C223—H223 | 0.95 |
C124—C127 | 1.509 (2) | C224—C225 | 1.388 (2) |
C127—H12A | 0.98 | C224—C227 | 1.5087 (19) |
C127—H12B | 0.98 | C227—H27A | 0.98 |
C127—H12C | 0.98 | C227—H27B | 0.98 |
C127—H12D | 0.98 | C227—H27C | 0.98 |
C127—H12E | 0.98 | C225—C226 | 1.3907 (18) |
C127—H12F | 0.98 | C225—H225 | 0.95 |
C125—C126 | 1.3880 (19) | C226—H226 | 0.95 |
C125—H125 | 0.95 | C22A—C22B | 1.4892 (17) |
C126—H126 | 0.95 | ||
C12—C11—C12B | 121.27 (13) | C121—C126—H126 | 119.7 |
C12—C11—H11 | 119.4 | C120—C12A—C16A | 118.66 (11) |
C12B—C11—H11 | 119.4 | C120—C12A—C12B | 125.22 (11) |
C13—C12—C11 | 120.26 (13) | C16A—C12A—C12B | 116.12 (11) |
C13—C12—H12 | 119.9 | C11—C12B—C14A | 118.04 (12) |
C11—C12—H12 | 119.9 | C11—C12B—C12A | 123.04 (12) |
C14—C13—C12 | 119.39 (13) | C14A—C12B—C12A | 118.87 (11) |
C14—C13—H13 | 120.3 | C22—C21—C22B | 120.78 (13) |
C12—C13—H13 | 120.3 | C22—C21—H21 | 119.6 |
C13—C14—C14A | 121.08 (13) | C22B—C21—H21 | 119.6 |
C13—C14—H14 | 119.5 | C23—C22—C21 | 119.76 (13) |
C14A—C14—H14 | 119.5 | C23—C22—H22 | 120.1 |
C14—C14A—C12B | 119.91 (12) | C21—C22—H22 | 120.1 |
C14—C14A—C15 | 121.33 (12) | C22—C23—C24 | 120.20 (13) |
C12B—C14A—C15 | 118.68 (12) | C22—C23—H23 | 119.9 |
C14A—C15—C16 | 108.42 (11) | C24—C23—H23 | 119.9 |
C14A—C15—H15A | 110.0 | C23—C24—C24A | 120.53 (13) |
C16—C15—H15A | 110.0 | C23—C24—H24 | 119.7 |
C14A—C15—H15B | 110.0 | C24A—C24—H24 | 119.7 |
C16—C15—H15B | 110.0 | C24—C24A—C22B | 119.46 (13) |
H15A—C15—H15B | 108.4 | C24—C24A—C25 | 121.97 (12) |
C16A—C16—C15 | 109.56 (11) | C22B—C24A—C25 | 118.49 (11) |
C16A—C16—H16A | 109.8 | C24A—C25—C26 | 108.59 (12) |
C15—C16—H16A | 109.8 | C24A—C25—H25A | 110.0 |
C16A—C16—H16B | 109.8 | C26—C25—H25A | 110.0 |
C15—C16—H16B | 109.8 | C24A—C25—H25B | 110.0 |
H16A—C16—H16B | 108.2 | C26—C25—H25B | 110.0 |
N17—C16A—C12A | 125.03 (12) | H25A—C25—H25B | 108.4 |
N17—C16A—C16 | 115.80 (11) | C26A—C26—C25 | 110.00 (11) |
C12A—C16A—C16 | 119.11 (11) | C26A—C26—H26A | 109.7 |
C16A—N17—C17A | 114.53 (11) | C25—C26—H26A | 109.7 |
N17—C17A—N18 | 125.70 (12) | C26A—C26—H26B | 109.7 |
N17—C17A—C11A | 126.69 (12) | C25—C26—H26B | 109.7 |
N18—C17A—C11A | 107.39 (11) | H26A—C26—H26B | 108.2 |
C17A—N18—N19 | 110.11 (10) | N27—C26A—C22A | 124.99 (11) |
C17A—N18—C181 | 129.74 (11) | N27—C26A—C26 | 116.41 (11) |
N19—N18—C181 | 119.48 (11) | C22A—C26A—C26 | 118.54 (11) |
C186—C181—C182 | 120.48 (13) | C26A—N27—C27A | 114.10 (11) |
C186—C181—N18 | 120.21 (12) | N27—C27A—N28 | 125.53 (11) |
C182—C181—N18 | 119.31 (12) | N27—C27A—C21A | 126.59 (11) |
C183—C182—C181 | 119.35 (13) | N28—C27A—C21A | 107.60 (11) |
C183—C182—H182 | 120.3 | C27A—N28—N29 | 109.92 (10) |
C181—C182—H182 | 120.3 | C27A—N28—C281 | 129.99 (11) |
C184—C183—C182 | 120.52 (14) | N29—N28—C281 | 119.14 (10) |
C184—C183—H183 | 119.7 | C282—C281—C286 | 119.92 (12) |
C182—C183—H183 | 119.7 | C282—C281—N28 | 119.04 (12) |
C185—C184—C183 | 119.62 (13) | C286—C281—N28 | 121.03 (12) |
C185—C184—H184 | 120.2 | C283—C282—C281 | 119.63 (14) |
C183—C184—H184 | 120.2 | C283—C282—H282 | 120.2 |
C184—C185—C186 | 120.85 (14) | C281—C282—H282 | 120.2 |
C184—C185—H185 | 119.6 | C282—C283—C284 | 120.94 (14) |
C186—C185—H185 | 119.6 | C282—C283—H283 | 119.5 |
C185—C186—C181 | 119.16 (13) | C284—C283—H283 | 119.5 |
C185—C186—H186 | 120.4 | C285—C284—C283 | 119.20 (14) |
C181—C186—H186 | 120.4 | C285—C284—H284 | 120.4 |
C110—N19—N18 | 107.42 (11) | C283—C284—H284 | 120.4 |
N19—C110—C11A | 110.36 (12) | C284—C285—C286 | 120.62 (13) |
N19—C110—C111 | 118.24 (12) | C284—C285—H285 | 119.7 |
C11A—C110—C111 | 131.40 (12) | C286—C285—H285 | 119.7 |
C110—C111—H11A | 109.5 | C285—C286—C281 | 119.68 (13) |
C110—C111—H11B | 109.5 | C285—C286—H286 | 120.2 |
H11A—C111—H11B | 109.5 | C281—C286—H286 | 120.2 |
C110—C111—H11C | 109.5 | C210—N29—N28 | 107.42 (10) |
H11A—C111—H11C | 109.5 | N29—C210—C21A | 110.65 (11) |
H11B—C111—H11C | 109.5 | N29—C210—C211 | 119.02 (11) |
C17A—C11A—C120 | 118.21 (12) | C21A—C210—C211 | 130.31 (12) |
C17A—C11A—C110 | 104.70 (11) | C210—C211—H21A | 109.5 |
C120—C11A—C110 | 136.79 (12) | C210—C211—H21B | 109.5 |
C12A—C120—C11A | 116.82 (11) | H21A—C211—H21B | 109.5 |
C12A—C120—C121 | 125.09 (12) | C210—C211—H21C | 109.5 |
C11A—C120—C121 | 118.03 (11) | H21A—C211—H21C | 109.5 |
C126—C121—C122 | 118.35 (12) | H21B—C211—H21C | 109.5 |
C126—C121—C120 | 120.50 (12) | C27A—C21A—C220 | 118.54 (11) |
C122—C121—C120 | 121.09 (12) | C27A—C21A—C210 | 104.38 (11) |
C123—C122—C121 | 120.56 (13) | C220—C21A—C210 | 136.84 (12) |
C123—C122—H122 | 119.7 | C22A—C220—C21A | 116.20 (11) |
C121—C122—H122 | 119.7 | C22A—C220—C221 | 122.43 (11) |
C122—C123—C124 | 121.18 (13) | C21A—C220—C221 | 121.17 (11) |
C122—C123—H123 | 119.4 | C226—C221—C222 | 118.31 (12) |
C124—C123—H123 | 119.4 | C226—C221—C220 | 122.17 (12) |
C125—C124—C123 | 117.92 (13) | C222—C221—C220 | 119.53 (12) |
C125—C124—C127 | 121.12 (14) | C223—C222—C221 | 120.84 (13) |
C123—C124—C127 | 120.95 (14) | C223—C222—H222 | 119.6 |
C124—C127—H12A | 109.5 | C221—C222—H222 | 119.6 |
C124—C127—H12B | 109.5 | C222—C223—C224 | 120.99 (13) |
H12A—C127—H12B | 109.5 | C222—C223—H223 | 119.5 |
C124—C127—H12C | 109.5 | C224—C223—H223 | 119.5 |
H12A—C127—H12C | 109.5 | C225—C224—C223 | 118.04 (12) |
H12B—C127—H12C | 109.5 | C225—C224—C227 | 121.68 (14) |
C124—C127—H12D | 109.5 | C223—C224—C227 | 120.28 (14) |
H12A—C127—H12D | 141.1 | C224—C227—H27A | 109.5 |
H12B—C127—H12D | 56.3 | C224—C227—H27B | 109.5 |
H12C—C127—H12D | 56.3 | H27A—C227—H27B | 109.5 |
C124—C127—H12E | 109.5 | C224—C227—H27C | 109.5 |
H12A—C127—H12E | 56.3 | H27A—C227—H27C | 109.5 |
H12B—C127—H12E | 141.1 | H27B—C227—H27C | 109.5 |
H12C—C127—H12E | 56.3 | C224—C225—C226 | 121.23 (13) |
H12D—C127—H12E | 109.5 | C224—C225—H225 | 119.4 |
C124—C127—H12F | 109.5 | C226—C225—H225 | 119.4 |
H12A—C127—H12F | 56.3 | C221—C226—C225 | 120.58 (13) |
H12B—C127—H12F | 56.3 | C221—C226—H226 | 119.7 |
H12C—C127—H12F | 141.1 | C225—C226—H226 | 119.7 |
H12D—C127—H12F | 109.5 | C220—C22A—C26A | 119.35 (11) |
H12E—C127—H12F | 109.5 | C220—C22A—C22B | 124.13 (11) |
C124—C125—C126 | 121.31 (13) | C26A—C22A—C22B | 116.50 (11) |
C124—C125—H125 | 119.3 | C21—C22B—C24A | 119.02 (12) |
C126—C125—H125 | 119.3 | C21—C22B—C22A | 122.33 (12) |
C125—C126—C121 | 120.65 (13) | C24A—C22B—C22A | 118.60 (12) |
C125—C126—H126 | 119.7 | ||
C12B—C11—C12—C13 | 0.0 (2) | C22B—C21—C22—C23 | −0.8 (2) |
C11—C12—C13—C14 | 1.5 (2) | C21—C22—C23—C24 | 3.6 (2) |
C12—C13—C14—C14A | −1.2 (2) | C22—C23—C24—C24A | −1.8 (2) |
C13—C14—C14A—C12B | −0.6 (2) | C23—C24—C24A—C22B | −2.7 (2) |
C13—C14—C14A—C15 | 176.16 (13) | C23—C24—C24A—C25 | 173.74 (13) |
C14—C14A—C15—C16 | −136.53 (13) | C24—C24A—C25—C26 | −138.76 (13) |
C12B—C14A—C15—C16 | 40.27 (16) | C22B—C24A—C25—C26 | 37.75 (17) |
C14A—C15—C16—C16A | −58.96 (14) | C24A—C25—C26—C26A | −58.16 (15) |
C15—C16—C16A—N17 | −139.54 (12) | C25—C26—C26A—N27 | −140.26 (12) |
C15—C16—C16A—C12A | 37.77 (16) | C25—C26—C26A—C22A | 37.05 (17) |
C12A—C16A—N17—C17A | −2.79 (18) | C22A—C26A—N27—C27A | −2.27 (19) |
C16—C16A—N17—C17A | 174.34 (11) | C26—C26A—N27—C27A | 174.85 (12) |
C16A—N17—C17A—N18 | −172.80 (12) | C26A—N27—C27A—N28 | −175.05 (12) |
C16A—N17—C17A—C11A | 1.12 (19) | C26A—N27—C27A—C21A | −1.89 (19) |
N17—C17A—N18—N19 | 173.26 (12) | N27—C27A—N28—N29 | 172.57 (12) |
C11A—C17A—N18—N19 | −1.63 (14) | C21A—C27A—N28—N29 | −1.68 (14) |
N17—C17A—N18—C181 | 2.9 (2) | N27—C27A—N28—C281 | 4.1 (2) |
C11A—C17A—N18—C181 | −172.01 (12) | C21A—C27A—N28—C281 | −170.15 (12) |
C17A—N18—C181—C186 | −29.8 (2) | C27A—N28—C281—C282 | 161.39 (14) |
N19—N18—C181—C186 | 160.56 (12) | N29—N28—C281—C282 | −6.19 (19) |
C17A—N18—C181—C182 | 150.26 (14) | C27A—N28—C281—C286 | −17.5 (2) |
N19—N18—C181—C182 | −19.36 (18) | N29—N28—C281—C286 | 174.89 (12) |
C186—C181—C182—C183 | 0.2 (2) | C286—C281—C282—C283 | 0.8 (2) |
N18—C181—C182—C183 | −179.84 (13) | N28—C281—C282—C283 | −178.09 (15) |
C181—C182—C183—C184 | 0.7 (2) | C281—C282—C283—C284 | 0.0 (3) |
C182—C183—C184—C185 | −0.7 (2) | C282—C283—C284—C285 | −0.5 (3) |
C183—C184—C185—C186 | −0.3 (2) | C283—C284—C285—C286 | 0.2 (2) |
C184—C185—C186—C181 | 1.3 (2) | C284—C285—C286—C281 | 0.7 (2) |
C182—C181—C186—C185 | −1.2 (2) | C282—C281—C286—C285 | −1.2 (2) |
N18—C181—C186—C185 | 178.85 (12) | N28—C281—C286—C285 | 177.74 (12) |
C17A—N18—N19—C110 | 1.60 (15) | C27A—N28—N29—C210 | 1.12 (15) |
C181—N18—N19—C110 | 173.12 (11) | C281—N28—N29—C210 | 171.03 (11) |
N18—N19—C110—C11A | −0.93 (15) | N28—N29—C210—C21A | −0.12 (15) |
N18—N19—C110—C111 | 179.63 (11) | N28—N29—C210—C211 | −178.76 (12) |
N17—C17A—C11A—C120 | 0.9 (2) | N27—C27A—C21A—C220 | 2.6 (2) |
N18—C17A—C11A—C120 | 175.73 (11) | N28—C27A—C21A—C220 | 176.74 (11) |
N17—C17A—C11A—C110 | −173.81 (13) | N27—C27A—C21A—C210 | −172.65 (12) |
N18—C17A—C11A—C110 | 1.01 (14) | N28—C27A—C21A—C210 | 1.52 (14) |
N19—C110—C11A—C17A | −0.04 (15) | N29—C210—C21A—C27A | −0.88 (15) |
C111—C110—C11A—C17A | 179.29 (14) | C211—C210—C21A—C27A | 177.57 (14) |
N19—C110—C11A—C120 | −173.24 (15) | N29—C210—C21A—C220 | −174.74 (15) |
C111—C110—C11A—C120 | 6.1 (3) | C211—C210—C21A—C220 | 3.7 (3) |
C17A—C11A—C120—C12A | −1.30 (18) | C27A—C21A—C220—C22A | 0.89 (18) |
C110—C11A—C120—C12A | 171.23 (14) | C210—C21A—C220—C22A | 174.12 (14) |
C17A—C11A—C120—C121 | −178.63 (11) | C27A—C21A—C220—C221 | −174.04 (11) |
C110—C11A—C120—C121 | −6.1 (2) | C210—C21A—C220—C221 | −0.8 (2) |
C12A—C120—C121—C126 | 123.80 (14) | C22A—C220—C221—C226 | 124.61 (14) |
C11A—C120—C121—C126 | −59.11 (17) | C21A—C220—C221—C226 | −60.78 (17) |
C12A—C120—C121—C122 | −58.94 (18) | C22A—C220—C221—C222 | −55.22 (17) |
C11A—C120—C121—C122 | 118.14 (14) | C21A—C220—C221—C222 | 119.39 (14) |
C126—C121—C122—C123 | −1.2 (2) | C226—C221—C222—C223 | −1.15 (19) |
C120—C121—C122—C123 | −178.51 (12) | C220—C221—C222—C223 | 178.68 (12) |
C121—C122—C123—C124 | 0.6 (2) | C221—C222—C223—C224 | 0.7 (2) |
C122—C123—C124—C125 | 0.6 (2) | C222—C223—C224—C225 | 0.4 (2) |
C122—C123—C124—C127 | −178.66 (14) | C222—C223—C224—C227 | −178.93 (13) |
C123—C124—C125—C126 | −1.2 (2) | C223—C224—C225—C226 | −1.0 (2) |
C127—C124—C125—C126 | 178.07 (14) | C227—C224—C225—C226 | 178.33 (13) |
C124—C125—C126—C121 | 0.6 (2) | C222—C221—C226—C225 | 0.57 (19) |
C122—C121—C126—C125 | 0.6 (2) | C220—C221—C226—C225 | −179.26 (12) |
C120—C121—C126—C125 | 177.95 (12) | C224—C225—C226—C221 | 0.5 (2) |
C11A—C120—C12A—C16A | −0.18 (18) | C21A—C220—C22A—C26A | −4.55 (18) |
C121—C120—C12A—C16A | 176.94 (12) | C221—C220—C22A—C26A | 170.32 (12) |
C11A—C120—C12A—C12B | 179.88 (12) | C21A—C220—C22A—C22B | 176.89 (12) |
C121—C120—C12A—C12B | −3.0 (2) | C221—C220—C22A—C22B | −8.2 (2) |
N17—C16A—C12A—C120 | 2.42 (19) | N27—C26A—C22A—C220 | 5.6 (2) |
C16—C16A—C12A—C120 | −174.63 (12) | C26—C26A—C22A—C220 | −171.43 (12) |
N17—C16A—C12A—C12B | −177.64 (12) | N27—C26A—C22A—C22B | −175.70 (12) |
C16—C16A—C12A—C12B | 5.32 (17) | C26—C26A—C22A—C22B | 7.24 (18) |
C12—C11—C12B—C14A | −1.80 (19) | C22—C21—C22B—C24A | −3.61 (19) |
C12—C11—C12B—C12A | −179.41 (12) | C22—C21—C22B—C22A | 178.84 (12) |
C14—C14A—C12B—C11 | 2.08 (19) | C24—C24A—C22B—C21 | 5.36 (19) |
C15—C14A—C12B—C11 | −174.77 (12) | C25—C24A—C22B—C21 | −171.24 (12) |
C14—C14A—C12B—C12A | 179.79 (12) | C24—C24A—C22B—C22A | −177.00 (12) |
C15—C14A—C12B—C12A | 2.94 (18) | C25—C24A—C22B—C22A | 6.40 (18) |
C120—C12A—C12B—C11 | −29.9 (2) | C220—C22A—C22B—C21 | −34.65 (19) |
C16A—C12A—C12B—C11 | 150.19 (12) | C26A—C22A—C22B—C21 | 146.75 (13) |
C120—C12A—C12B—C14A | 152.55 (13) | C220—C22A—C22B—C24A | 147.80 (13) |
C16A—C12A—C12B—C14A | −27.40 (17) | C26A—C22A—C22B—C24A | −30.80 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···Cg6i | 0.95 | 2.89 | 3.662 (2) | 136 |
C122—H122···Cg7 | 0.95 | 2.75 | 3.412 (2) | 127 |
C125—H125···Cg8ii | 0.95 | 2.87 | 3.772 (2) | 160 |
C222—H222···Cg9 | 0.95 | 2.75 | 3.322 (2) | 119 |
C225—H225···Cg10iii | 0.95 | 2.93 | 3.834 (2) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
C28H23N3O | F(000) = 3520 |
Mr = 417.49 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 19715 reflections |
a = 18.0854 (3) Å | θ = 3.0–27.5° |
b = 21.2296 (5) Å | µ = 0.08 mm−1 |
c = 23.8007 (5) Å | T = 120 K |
β = 108.258 (1)° | Lath, colourless |
V = 8678.1 (3) Å3 | 0.90 × 0.30 × 0.10 mm |
Z = 16 |
Bruker-Nonius KappaCCD diffractometer | 19715 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 8289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.166 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ & ω scans | h = −23→22 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −27→26 |
Tmin = 0.934, Tmax = 0.992 | l = −30→30 |
99695 measured reflections |
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)] = 0.096 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3 |
19715 reflections | (Δ/σ)max < 0.001 |
1161 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C28H23N3O | V = 8678.1 (3) Å3 |
Mr = 417.49 | Z = 16 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.0854 (3) Å | µ = 0.08 mm−1 |
b = 21.2296 (5) Å | T = 120 K |
c = 23.8007 (5) Å | 0.90 × 0.30 × 0.10 mm |
β = 108.258 (1)° |
Bruker-Nonius KappaCCD diffractometer | 19715 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 8289 reflections with I > 2σ(I) |
Tmin = 0.934, Tmax = 0.992 | Rint = 0.166 |
99695 measured reflections |
R[F2 > 2σ(F2)] = 0.096 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.26 e Å−3 |
19715 reflections | Δρmin = −0.30 e Å−3 |
1161 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | 1.00741 (15) | 0.77687 (13) | 0.58326 (12) | 0.0341 (7) | |
C12 | 0.98413 (16) | 0.82911 (14) | 0.54727 (14) | 0.0431 (8) | |
C13 | 0.97377 (17) | 0.88632 (14) | 0.57157 (14) | 0.0483 (8) | |
C14 | 0.98758 (16) | 0.89140 (14) | 0.63177 (14) | 0.0448 (8) | |
C14A | 1.01138 (14) | 0.83941 (13) | 0.66848 (12) | 0.0332 (7) | |
C15 | 1.03120 (15) | 0.84432 (12) | 0.73444 (12) | 0.0367 (7) | |
C16 | 1.10624 (14) | 0.80866 (12) | 0.76321 (12) | 0.0335 (7) | |
C16A | 1.09516 (14) | 0.74088 (12) | 0.74424 (12) | 0.0282 (6) | |
N17 | 1.12998 (11) | 0.69846 (10) | 0.78567 (9) | 0.0293 (5) | |
C17A | 1.11599 (14) | 0.63841 (13) | 0.76781 (11) | 0.0269 (6) | |
N18 | 1.14384 (12) | 0.58613 (10) | 0.80153 (9) | 0.0319 (6) | |
C181 | 1.19480 (15) | 0.58010 (13) | 0.86040 (12) | 0.0346 (7) | |
C182 | 1.23896 (17) | 0.52594 (15) | 0.87633 (13) | 0.0498 (8) | |
C183 | 1.28718 (18) | 0.51901 (17) | 0.93440 (14) | 0.0598 (10) | |
C184 | 1.29183 (18) | 0.56563 (17) | 0.97557 (14) | 0.0542 (9) | |
C185 | 1.24901 (17) | 0.61971 (16) | 0.95893 (13) | 0.0477 (8) | |
C186 | 1.20052 (15) | 0.62750 (14) | 0.90124 (12) | 0.0385 (7) | |
N19 | 1.11322 (13) | 0.53242 (10) | 0.77010 (10) | 0.0365 (6) | |
C110 | 1.06836 (15) | 0.55073 (12) | 0.71741 (11) | 0.0300 (7) | |
C111 | 1.02341 (15) | 0.50250 (12) | 0.67412 (11) | 0.0369 (7) | |
C11A | 1.06866 (14) | 0.61779 (12) | 0.71247 (11) | 0.0261 (6) | |
C120 | 1.03341 (13) | 0.66284 (12) | 0.66895 (11) | 0.0253 (6) | |
C121 | 0.98514 (14) | 0.63964 (11) | 0.60980 (11) | 0.0245 (6) | |
C122 | 0.90573 (14) | 0.64941 (12) | 0.58749 (11) | 0.0280 (6) | |
C123 | 0.86207 (14) | 0.62503 (12) | 0.53299 (11) | 0.0297 (7) | |
C124 | 0.89869 (15) | 0.59023 (12) | 0.49981 (11) | 0.0300 (7) | |
O124 | 0.86229 (10) | 0.56352 (9) | 0.44608 (7) | 0.0395 (5) | |
C127 | 0.77964 (15) | 0.56804 (14) | 0.42293 (12) | 0.0456 (8) | |
C125 | 0.97852 (14) | 0.58127 (12) | 0.52145 (11) | 0.0297 (6) | |
C126 | 1.02093 (14) | 0.60467 (12) | 0.57579 (11) | 0.0276 (6) | |
C12A | 1.04837 (13) | 0.72620 (12) | 0.68499 (11) | 0.0265 (6) | |
C12B | 1.02046 (14) | 0.78070 (12) | 0.64431 (11) | 0.0281 (6) | |
C21 | 0.66787 (14) | 0.35957 (12) | 0.69753 (11) | 0.0302 (6) | |
C22 | 0.64313 (15) | 0.41183 (13) | 0.66281 (12) | 0.0347 (7) | |
C23 | 0.63352 (15) | 0.46876 (13) | 0.68777 (12) | 0.0367 (7) | |
C24 | 0.64986 (14) | 0.47302 (12) | 0.74855 (12) | 0.0327 (7) | |
C24A | 0.67546 (14) | 0.42042 (13) | 0.78465 (11) | 0.0288 (6) | |
C25 | 0.69849 (15) | 0.42512 (12) | 0.85102 (11) | 0.0341 (7) | |
C26 | 0.77180 (15) | 0.38637 (12) | 0.87772 (11) | 0.0327 (7) | |
C26A | 0.75713 (14) | 0.31944 (12) | 0.85787 (11) | 0.0268 (6) | |
N27 | 0.78800 (11) | 0.27572 (10) | 0.89894 (9) | 0.0271 (5) | |
C27A | 0.77232 (14) | 0.21626 (13) | 0.87975 (11) | 0.0266 (6) | |
N28 | 0.79484 (12) | 0.16321 (10) | 0.91359 (9) | 0.0306 (5) | |
C281 | 0.83816 (14) | 0.15588 (13) | 0.97451 (11) | 0.0305 (7) | |
C282 | 0.83525 (15) | 0.09863 (13) | 1.00180 (12) | 0.0382 (7) | |
C283 | 0.87902 (17) | 0.08979 (15) | 1.06026 (13) | 0.0446 (8) | |
C284 | 0.92545 (16) | 0.13783 (15) | 1.09188 (13) | 0.0436 (8) | |
C285 | 0.92764 (15) | 0.19497 (14) | 1.06483 (12) | 0.0395 (7) | |
C286 | 0.88406 (15) | 0.20429 (13) | 1.00604 (11) | 0.0345 (7) | |
N29 | 0.76457 (13) | 0.11051 (10) | 0.88073 (10) | 0.0372 (6) | |
C210 | 0.72472 (15) | 0.12942 (13) | 0.82712 (12) | 0.0339 (7) | |
C211 | 0.68576 (18) | 0.08099 (13) | 0.78146 (13) | 0.0524 (9) | |
C21A | 0.72712 (14) | 0.19671 (12) | 0.82320 (11) | 0.0267 (6) | |
C220 | 0.69308 (14) | 0.24345 (12) | 0.78049 (11) | 0.0252 (6) | |
C221 | 0.64050 (14) | 0.22418 (12) | 0.72115 (11) | 0.0250 (6) | |
C222 | 0.56272 (14) | 0.24247 (12) | 0.70157 (11) | 0.0285 (6) | |
C223 | 0.51414 (14) | 0.22522 (12) | 0.64587 (11) | 0.0302 (7) | |
C224 | 0.54350 (14) | 0.18907 (13) | 0.60937 (11) | 0.0313 (7) | |
O224 | 0.50175 (10) | 0.16956 (9) | 0.55337 (8) | 0.0421 (5) | |
C227 | 0.42471 (15) | 0.19283 (15) | 0.52890 (11) | 0.0472 (8) | |
C225 | 0.62082 (15) | 0.17007 (13) | 0.62857 (12) | 0.0376 (7) | |
C226 | 0.66837 (15) | 0.18781 (12) | 0.68358 (11) | 0.0342 (7) | |
C22A | 0.71046 (13) | 0.30629 (12) | 0.79829 (10) | 0.0245 (6) | |
C22B | 0.68344 (13) | 0.36211 (12) | 0.75905 (11) | 0.0263 (6) | |
C31 | 0.51657 (15) | 0.88414 (13) | 0.59611 (12) | 0.0341 (7) | |
C32 | 0.49439 (16) | 0.93824 (14) | 0.56300 (13) | 0.0417 (8) | |
C33 | 0.48605 (17) | 0.99434 (14) | 0.59015 (14) | 0.0468 (8) | |
C34 | 0.50174 (15) | 0.99583 (13) | 0.65128 (14) | 0.0415 (8) | |
C34A | 0.52449 (14) | 0.94154 (13) | 0.68507 (12) | 0.0323 (7) | |
C35 | 0.54609 (15) | 0.94297 (12) | 0.75123 (11) | 0.0354 (7) | |
C36 | 0.61947 (15) | 0.90412 (11) | 0.77744 (11) | 0.0331 (7) | |
C36A | 0.60457 (14) | 0.83765 (12) | 0.75541 (11) | 0.0266 (6) | |
N37 | 0.63600 (11) | 0.79272 (10) | 0.79477 (9) | 0.0275 (5) | |
C37A | 0.61833 (14) | 0.73419 (12) | 0.77441 (11) | 0.0254 (6) | |
N38 | 0.63931 (12) | 0.67955 (10) | 0.80653 (9) | 0.0292 (5) | |
C381 | 0.68499 (14) | 0.66857 (13) | 0.86639 (11) | 0.0297 (7) | |
C382 | 0.68622 (16) | 0.60856 (13) | 0.88990 (12) | 0.0386 (7) | |
C383 | 0.73102 (17) | 0.59687 (14) | 0.94765 (12) | 0.0433 (8) | |
C384 | 0.77375 (16) | 0.64437 (15) | 0.98227 (13) | 0.0422 (8) | |
C385 | 0.77183 (15) | 0.70376 (15) | 0.95907 (12) | 0.0430 (8) | |
C386 | 0.72745 (15) | 0.71644 (14) | 0.90096 (12) | 0.0367 (7) | |
N39 | 0.60248 (12) | 0.62852 (10) | 0.77286 (10) | 0.0341 (6) | |
C310 | 0.56110 (15) | 0.65065 (12) | 0.72077 (11) | 0.0301 (7) | |
C311 | 0.51080 (16) | 0.60658 (12) | 0.67589 (12) | 0.0413 (8) | |
C31A | 0.56981 (13) | 0.71743 (12) | 0.71819 (11) | 0.0247 (6) | |
C320 | 0.53844 (13) | 0.76520 (12) | 0.67657 (11) | 0.0240 (6) | |
C321 | 0.48690 (14) | 0.74555 (11) | 0.61645 (11) | 0.0245 (6) | |
C322 | 0.40793 (14) | 0.75840 (11) | 0.59672 (10) | 0.0264 (6) | |
C323 | 0.36069 (14) | 0.73730 (12) | 0.54184 (11) | 0.0294 (6) | |
C324 | 0.39281 (14) | 0.70241 (12) | 0.50619 (11) | 0.0281 (6) | |
O324 | 0.35200 (10) | 0.67856 (9) | 0.45186 (7) | 0.0392 (5) | |
C327 | 0.27383 (14) | 0.69774 (14) | 0.42595 (11) | 0.0424 (8) | |
C325 | 0.47151 (14) | 0.68903 (12) | 0.52530 (11) | 0.0327 (7) | |
C326 | 0.51822 (14) | 0.71012 (12) | 0.57969 (11) | 0.0298 (7) | |
C32A | 0.55702 (14) | 0.82725 (12) | 0.69540 (11) | 0.0256 (6) | |
C32B | 0.53142 (14) | 0.88419 (12) | 0.65760 (11) | 0.0277 (6) | |
C41 | 0.83177 (14) | 0.75472 (13) | 0.80761 (12) | 0.0330 (7) | |
C42 | 0.85372 (15) | 0.80687 (14) | 0.84373 (12) | 0.0393 (7) | |
C43 | 0.85862 (15) | 0.86521 (14) | 0.81973 (13) | 0.0422 (8) | |
C44 | 0.84067 (15) | 0.87158 (13) | 0.75913 (13) | 0.0384 (7) | |
C44A | 0.81909 (14) | 0.81973 (13) | 0.72203 (12) | 0.0315 (7) | |
C45 | 0.79793 (15) | 0.82619 (13) | 0.65602 (11) | 0.0372 (7) | |
C46 | 0.72750 (14) | 0.78486 (12) | 0.62703 (11) | 0.0342 (7) | |
C46A | 0.74563 (14) | 0.71785 (12) | 0.64609 (11) | 0.0269 (6) | |
N47 | 0.71628 (11) | 0.67451 (10) | 0.60418 (9) | 0.0277 (5) | |
C47A | 0.73691 (14) | 0.61516 (12) | 0.62144 (11) | 0.0260 (6) | |
N48 | 0.71803 (11) | 0.56221 (10) | 0.58654 (9) | 0.0278 (5) | |
C481 | 0.66704 (14) | 0.55344 (13) | 0.52815 (11) | 0.0304 (7) | |
C482 | 0.65134 (16) | 0.49224 (14) | 0.50691 (12) | 0.0428 (8) | |
C483 | 0.60279 (18) | 0.48269 (15) | 0.44961 (13) | 0.0530 (9) | |
C484 | 0.56909 (17) | 0.53269 (15) | 0.41384 (13) | 0.0462 (8) | |
C485 | 0.58467 (16) | 0.59313 (15) | 0.43548 (12) | 0.0439 (8) | |
C486 | 0.63383 (15) | 0.60373 (13) | 0.49261 (12) | 0.0358 (7) | |
N49 | 0.75598 (12) | 0.51016 (10) | 0.61770 (9) | 0.0313 (5) | |
C410 | 0.79562 (14) | 0.52951 (12) | 0.67119 (11) | 0.0291 (6) | |
C411 | 0.84154 (15) | 0.48245 (12) | 0.71485 (11) | 0.0389 (7) | |
C41A | 0.78514 (13) | 0.59607 (12) | 0.67671 (11) | 0.0262 (6) | |
C420 | 0.81369 (13) | 0.64205 (12) | 0.72099 (10) | 0.0247 (6) | |
C421 | 0.86213 (14) | 0.62013 (12) | 0.78058 (11) | 0.0252 (6) | |
C422 | 0.94078 (14) | 0.63338 (12) | 0.80292 (11) | 0.0304 (7) | |
C423 | 0.98573 (15) | 0.61046 (12) | 0.85775 (11) | 0.0327 (7) | |
C424 | 0.95112 (14) | 0.57399 (13) | 0.89096 (11) | 0.0307 (7) | |
O424 | 0.98921 (10) | 0.54886 (9) | 0.94533 (7) | 0.0391 (5) | |
C427 | 1.07127 (15) | 0.55918 (14) | 0.96887 (12) | 0.0441 (8) | |
C425 | 0.87197 (15) | 0.56124 (13) | 0.86938 (11) | 0.0351 (7) | |
C426 | 0.82856 (15) | 0.58380 (12) | 0.81480 (11) | 0.0330 (7) | |
C42A | 0.79236 (13) | 0.70467 (12) | 0.70535 (11) | 0.0254 (6) | |
C42B | 0.81531 (14) | 0.75967 (12) | 0.74612 (11) | 0.0287 (6) | |
H11 | 1.0147 | 0.7378 | 0.5663 | 0.041* | |
H12 | 0.9753 | 0.8257 | 0.5059 | 0.052* | |
H13 | 0.9572 | 0.9221 | 0.5468 | 0.058* | |
H14 | 0.9808 | 0.9309 | 0.6483 | 0.054* | |
H15A | 0.9886 | 0.8262 | 0.7472 | 0.044* | |
H15B | 1.0376 | 0.8891 | 0.7466 | 0.044* | |
H16A | 1.1491 | 0.8274 | 0.7512 | 0.040* | |
H16B | 1.1201 | 0.8115 | 0.8068 | 0.040* | |
H182 | 1.2364 | 0.4939 | 0.8480 | 0.060* | |
H183 | 1.3172 | 0.4817 | 0.9457 | 0.072* | |
H184 | 1.3245 | 0.5604 | 1.0152 | 0.065* | |
H185 | 1.2526 | 0.6521 | 0.9872 | 0.057* | |
H186 | 1.1714 | 0.6652 | 0.8899 | 0.046* | |
H11A | 1.0462 | 0.4980 | 0.6420 | 0.055* | |
H11B | 0.9691 | 0.5160 | 0.6578 | 0.055* | |
H11C | 1.0256 | 0.4620 | 0.6943 | 0.055* | |
H122 | 0.8804 | 0.6733 | 0.6099 | 0.034* | |
H123 | 0.8075 | 0.6321 | 0.5185 | 0.036* | |
H12A | 0.7564 | 0.5513 | 0.4519 | 0.068* | |
H12B | 0.7611 | 0.5436 | 0.3862 | 0.068* | |
H12C | 0.7646 | 0.6123 | 0.4148 | 0.068* | |
H125 | 1.0042 | 0.5587 | 0.4985 | 0.036* | |
H126 | 1.0754 | 0.5970 | 0.5905 | 0.033* | |
H21 | 0.6746 | 0.3209 | 0.6796 | 0.036* | |
H22 | 0.6325 | 0.4088 | 0.6212 | 0.042* | |
H23 | 0.6159 | 0.5047 | 0.6635 | 0.044* | |
H24 | 0.6436 | 0.5122 | 0.7659 | 0.039* | |
H25A | 0.6559 | 0.4090 | 0.8650 | 0.041* | |
H25B | 0.7083 | 0.4697 | 0.8634 | 0.041* | |
H26A | 0.8149 | 0.4038 | 0.8651 | 0.039* | |
H26B | 0.7872 | 0.3884 | 0.9214 | 0.039* | |
H282 | 0.8033 | 0.0656 | 0.9803 | 0.046* | |
H283 | 0.8772 | 0.0505 | 1.0789 | 0.053* | |
H284 | 0.9557 | 0.1315 | 1.1320 | 0.052* | |
H285 | 0.9591 | 0.2281 | 1.0866 | 0.047* | |
H286 | 0.8857 | 0.2437 | 0.9875 | 0.041* | |
H21A | 0.7143 | 0.0770 | 0.7528 | 0.079* | |
H21B | 0.6321 | 0.0941 | 0.7610 | 0.079* | |
H21C | 0.6855 | 0.0403 | 0.8009 | 0.079* | |
H222 | 0.5425 | 0.2672 | 0.7267 | 0.034* | |
H223 | 0.4612 | 0.2382 | 0.6330 | 0.036* | |
H27A | 0.3932 | 0.1793 | 0.5535 | 0.071* | |
H27B | 0.4020 | 0.1763 | 0.4887 | 0.071* | |
H27C | 0.4258 | 0.2389 | 0.5276 | 0.071* | |
H225 | 0.6409 | 0.1448 | 0.6037 | 0.045* | |
H226 | 0.7213 | 0.1749 | 0.6962 | 0.041* | |
H31 | 0.5219 | 0.8460 | 0.5768 | 0.041* | |
H32 | 0.4848 | 0.9370 | 0.5214 | 0.050* | |
H33 | 0.4698 | 1.0314 | 0.5673 | 0.056* | |
H34 | 0.4969 | 1.0343 | 0.6701 | 0.050* | |
H35A | 0.5031 | 0.9255 | 0.7638 | 0.042* | |
H35B | 0.5553 | 0.9870 | 0.7655 | 0.042* | |
H36A | 0.6628 | 0.9223 | 0.7657 | 0.040* | |
H36B | 0.6344 | 0.9047 | 0.8212 | 0.040* | |
H382 | 0.6564 | 0.5757 | 0.8664 | 0.046* | |
H383 | 0.7323 | 0.5557 | 0.9636 | 0.052* | |
H384 | 0.8044 | 0.6361 | 1.0220 | 0.051* | |
H385 | 0.8012 | 0.7366 | 0.9830 | 0.052* | |
H386 | 0.7264 | 0.7577 | 0.8852 | 0.044* | |
H31A | 0.5310 | 0.6029 | 0.6423 | 0.062* | |
H31B | 0.4575 | 0.6229 | 0.6620 | 0.062* | |
H31C | 0.5109 | 0.5650 | 0.6939 | 0.062* | |
H322 | 0.3855 | 0.7821 | 0.6211 | 0.032* | |
H323 | 0.3066 | 0.7468 | 0.5289 | 0.035* | |
H32A | 0.2439 | 0.6876 | 0.4527 | 0.064* | |
H32B | 0.2513 | 0.6757 | 0.3883 | 0.064* | |
H32C | 0.2721 | 0.7433 | 0.4189 | 0.064* | |
H325 | 0.4936 | 0.6651 | 0.5008 | 0.039* | |
H326 | 0.5722 | 0.7005 | 0.5924 | 0.036* | |
H41 | 0.8278 | 0.7149 | 0.8247 | 0.040* | |
H42 | 0.8655 | 0.8025 | 0.8853 | 0.047* | |
H43 | 0.8743 | 0.9009 | 0.8447 | 0.051* | |
H44 | 0.8431 | 0.9120 | 0.7426 | 0.046* | |
H45A | 0.8423 | 0.8130 | 0.6428 | 0.045* | |
H45B | 0.7856 | 0.8707 | 0.6444 | 0.045* | |
H46A | 0.6824 | 0.7996 | 0.6386 | 0.041* | |
H46B | 0.7138 | 0.7879 | 0.5834 | 0.041* | |
H482 | 0.6736 | 0.4574 | 0.5314 | 0.051* | |
H483 | 0.5926 | 0.4410 | 0.4348 | 0.064* | |
H484 | 0.5355 | 0.5256 | 0.3748 | 0.055* | |
H485 | 0.5616 | 0.6279 | 0.4111 | 0.053* | |
H486 | 0.6445 | 0.6455 | 0.5071 | 0.043* | |
H41A | 0.8131 | 0.4712 | 0.7423 | 0.058* | |
H41B | 0.8921 | 0.5006 | 0.7370 | 0.058* | |
H41C | 0.8496 | 0.4446 | 0.6939 | 0.058* | |
H422 | 0.9646 | 0.6586 | 0.7804 | 0.037* | |
H423 | 1.0398 | 0.6197 | 0.8724 | 0.039* | |
H42A | 1.0971 | 0.5416 | 0.9418 | 0.066* | |
H42B | 1.0913 | 0.5386 | 1.0075 | 0.066* | |
H42C | 1.0816 | 0.6045 | 0.9734 | 0.066* | |
H425 | 0.8478 | 0.5370 | 0.8923 | 0.042* | |
H426 | 0.7745 | 0.5744 | 0.8002 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0368 (16) | 0.0295 (18) | 0.0358 (17) | −0.0032 (13) | 0.0113 (14) | 0.0012 (14) |
C12 | 0.0459 (19) | 0.039 (2) | 0.0424 (19) | −0.0009 (15) | 0.0102 (15) | 0.0093 (16) |
C13 | 0.053 (2) | 0.032 (2) | 0.055 (2) | 0.0008 (15) | 0.0087 (17) | 0.0127 (17) |
C14 | 0.0407 (18) | 0.0277 (19) | 0.059 (2) | 0.0026 (14) | 0.0056 (16) | −0.0003 (16) |
C14A | 0.0258 (15) | 0.0254 (18) | 0.0430 (18) | −0.0014 (12) | 0.0030 (13) | −0.0018 (15) |
C15 | 0.0347 (16) | 0.0255 (17) | 0.0459 (19) | −0.0018 (13) | 0.0067 (14) | −0.0110 (14) |
C16 | 0.0316 (15) | 0.0290 (18) | 0.0360 (17) | −0.0017 (13) | 0.0048 (13) | −0.0083 (13) |
C16A | 0.0224 (14) | 0.0275 (18) | 0.0355 (17) | −0.0026 (12) | 0.0102 (13) | −0.0012 (14) |
N17 | 0.0277 (12) | 0.0264 (14) | 0.0325 (13) | −0.0020 (10) | 0.0076 (10) | −0.0023 (12) |
C17A | 0.0250 (14) | 0.0263 (17) | 0.0286 (16) | 0.0015 (12) | 0.0074 (12) | 0.0012 (13) |
N18 | 0.0342 (13) | 0.0302 (14) | 0.0251 (13) | −0.0019 (11) | 0.0005 (11) | 0.0000 (11) |
C181 | 0.0314 (16) | 0.0399 (19) | 0.0278 (17) | −0.0040 (14) | 0.0025 (13) | 0.0072 (15) |
C182 | 0.052 (2) | 0.049 (2) | 0.040 (2) | 0.0056 (17) | 0.0038 (16) | 0.0073 (16) |
C183 | 0.059 (2) | 0.062 (3) | 0.047 (2) | 0.0094 (18) | −0.0010 (18) | 0.023 (2) |
C184 | 0.048 (2) | 0.070 (3) | 0.0329 (19) | −0.0160 (19) | −0.0039 (16) | 0.0152 (19) |
C185 | 0.0477 (19) | 0.055 (2) | 0.0347 (19) | −0.0221 (17) | 0.0044 (15) | 0.0046 (16) |
C186 | 0.0371 (17) | 0.046 (2) | 0.0295 (17) | −0.0109 (14) | 0.0058 (14) | 0.0055 (15) |
N19 | 0.0403 (14) | 0.0313 (15) | 0.0333 (14) | −0.0032 (11) | 0.0050 (12) | 0.0013 (12) |
C110 | 0.0315 (16) | 0.0288 (18) | 0.0286 (16) | −0.0035 (12) | 0.0079 (13) | 0.0001 (13) |
C111 | 0.0431 (17) | 0.0251 (17) | 0.0364 (17) | −0.0052 (13) | 0.0038 (14) | −0.0008 (14) |
C11A | 0.0243 (14) | 0.0277 (18) | 0.0249 (15) | −0.0039 (12) | 0.0057 (12) | −0.0037 (13) |
C120 | 0.0199 (13) | 0.0302 (18) | 0.0252 (15) | −0.0003 (12) | 0.0060 (12) | 0.0001 (13) |
C121 | 0.0245 (14) | 0.0235 (16) | 0.0239 (15) | −0.0031 (12) | 0.0056 (12) | 0.0019 (12) |
C122 | 0.0272 (15) | 0.0292 (17) | 0.0281 (16) | −0.0024 (12) | 0.0095 (13) | −0.0020 (13) |
C123 | 0.0222 (14) | 0.0370 (18) | 0.0270 (16) | −0.0037 (12) | 0.0038 (12) | 0.0044 (13) |
C124 | 0.0353 (17) | 0.0315 (17) | 0.0206 (15) | −0.0064 (13) | 0.0051 (13) | 0.0013 (13) |
O124 | 0.0343 (11) | 0.0556 (14) | 0.0238 (11) | −0.0085 (9) | 0.0019 (9) | −0.0065 (10) |
C127 | 0.0335 (18) | 0.064 (2) | 0.0305 (17) | −0.0112 (15) | −0.0019 (14) | −0.0043 (15) |
C125 | 0.0331 (16) | 0.0331 (17) | 0.0244 (15) | −0.0012 (13) | 0.0110 (13) | −0.0020 (13) |
C126 | 0.0243 (14) | 0.0298 (17) | 0.0270 (16) | −0.0011 (12) | 0.0056 (12) | 0.0028 (13) |
C12A | 0.0212 (14) | 0.0271 (17) | 0.0309 (16) | −0.0007 (12) | 0.0080 (12) | −0.0022 (13) |
C12B | 0.0245 (14) | 0.0236 (17) | 0.0345 (17) | −0.0029 (12) | 0.0066 (13) | 0.0016 (13) |
C21 | 0.0358 (16) | 0.0263 (17) | 0.0296 (16) | −0.0040 (13) | 0.0121 (13) | −0.0027 (13) |
C22 | 0.0387 (16) | 0.0372 (19) | 0.0267 (16) | −0.0018 (14) | 0.0082 (13) | 0.0041 (14) |
C23 | 0.0360 (16) | 0.0337 (19) | 0.0370 (18) | −0.0012 (13) | 0.0066 (14) | 0.0095 (15) |
C24 | 0.0311 (15) | 0.0254 (17) | 0.0390 (18) | 0.0006 (12) | 0.0073 (13) | −0.0016 (14) |
C24A | 0.0251 (14) | 0.0330 (18) | 0.0271 (15) | −0.0046 (12) | 0.0066 (12) | −0.0004 (14) |
C25 | 0.0405 (17) | 0.0276 (17) | 0.0324 (17) | −0.0017 (13) | 0.0086 (14) | −0.0072 (13) |
C26 | 0.0378 (16) | 0.0302 (18) | 0.0262 (15) | −0.0044 (13) | 0.0044 (13) | −0.0051 (13) |
C26A | 0.0247 (14) | 0.0294 (17) | 0.0263 (15) | −0.0017 (12) | 0.0080 (12) | −0.0031 (13) |
N27 | 0.0268 (12) | 0.0266 (14) | 0.0265 (13) | −0.0008 (10) | 0.0062 (10) | −0.0002 (11) |
C27A | 0.0246 (14) | 0.0293 (18) | 0.0269 (16) | 0.0023 (12) | 0.0094 (12) | 0.0015 (14) |
N28 | 0.0318 (13) | 0.0291 (15) | 0.0274 (13) | −0.0002 (11) | 0.0041 (11) | 0.0013 (11) |
C281 | 0.0260 (15) | 0.0400 (19) | 0.0266 (16) | 0.0050 (13) | 0.0096 (13) | 0.0051 (14) |
C282 | 0.0358 (16) | 0.040 (2) | 0.0362 (18) | 0.0005 (14) | 0.0083 (14) | 0.0083 (15) |
C283 | 0.0494 (19) | 0.047 (2) | 0.0381 (19) | 0.0146 (16) | 0.0152 (16) | 0.0163 (16) |
C284 | 0.0401 (18) | 0.057 (2) | 0.0306 (17) | 0.0108 (16) | 0.0070 (14) | 0.0092 (17) |
C285 | 0.0366 (17) | 0.048 (2) | 0.0298 (17) | 0.0056 (15) | 0.0051 (14) | 0.0006 (15) |
C286 | 0.0309 (15) | 0.0405 (19) | 0.0312 (17) | 0.0056 (14) | 0.0083 (13) | 0.0044 (14) |
N29 | 0.0405 (14) | 0.0282 (15) | 0.0376 (15) | −0.0025 (11) | 0.0046 (12) | −0.0012 (12) |
C210 | 0.0336 (16) | 0.0281 (18) | 0.0367 (18) | −0.0027 (13) | 0.0063 (14) | −0.0008 (14) |
C211 | 0.064 (2) | 0.0295 (19) | 0.051 (2) | −0.0072 (16) | −0.0005 (17) | −0.0030 (16) |
C21A | 0.0253 (14) | 0.0263 (18) | 0.0281 (16) | −0.0015 (12) | 0.0079 (12) | −0.0020 (13) |
C220 | 0.0238 (14) | 0.0258 (17) | 0.0269 (15) | −0.0003 (12) | 0.0092 (12) | −0.0019 (13) |
C221 | 0.0238 (14) | 0.0248 (16) | 0.0247 (15) | −0.0046 (11) | 0.0052 (12) | −0.0014 (12) |
C222 | 0.0299 (16) | 0.0309 (17) | 0.0269 (16) | −0.0007 (12) | 0.0119 (13) | −0.0005 (13) |
C223 | 0.0234 (14) | 0.0370 (18) | 0.0309 (16) | −0.0018 (12) | 0.0097 (13) | 0.0012 (13) |
C224 | 0.0302 (16) | 0.0345 (18) | 0.0263 (16) | −0.0032 (13) | 0.0045 (13) | −0.0003 (13) |
O224 | 0.0315 (11) | 0.0603 (15) | 0.0289 (11) | 0.0018 (9) | 0.0012 (9) | −0.0095 (10) |
C227 | 0.0299 (17) | 0.082 (3) | 0.0273 (17) | −0.0027 (16) | 0.0050 (14) | −0.0014 (16) |
C225 | 0.0331 (16) | 0.045 (2) | 0.0331 (17) | 0.0051 (13) | 0.0083 (14) | −0.0128 (14) |
C226 | 0.0271 (15) | 0.0369 (18) | 0.0354 (17) | 0.0051 (13) | 0.0049 (13) | −0.0055 (14) |
C22A | 0.0228 (14) | 0.0273 (17) | 0.0249 (15) | 0.0003 (12) | 0.0095 (12) | 0.0019 (13) |
C22B | 0.0244 (14) | 0.0286 (17) | 0.0271 (15) | −0.0035 (12) | 0.0097 (12) | −0.0018 (13) |
C31 | 0.0387 (16) | 0.0297 (18) | 0.0345 (17) | −0.0017 (13) | 0.0125 (14) | 0.0011 (14) |
C32 | 0.0483 (19) | 0.038 (2) | 0.0370 (18) | −0.0026 (15) | 0.0107 (15) | 0.0064 (16) |
C33 | 0.055 (2) | 0.032 (2) | 0.047 (2) | 0.0004 (15) | 0.0076 (16) | 0.0114 (16) |
C34 | 0.0407 (18) | 0.0268 (19) | 0.052 (2) | 0.0023 (14) | 0.0080 (15) | 0.0005 (16) |
C34A | 0.0316 (16) | 0.0256 (18) | 0.0368 (17) | −0.0033 (13) | 0.0067 (13) | −0.0022 (14) |
C35 | 0.0407 (17) | 0.0293 (18) | 0.0319 (17) | 0.0002 (13) | 0.0055 (14) | −0.0085 (13) |
C36 | 0.0351 (16) | 0.0270 (17) | 0.0323 (16) | −0.0018 (13) | 0.0036 (13) | −0.0057 (13) |
C36A | 0.0240 (14) | 0.0249 (17) | 0.0305 (16) | −0.0015 (12) | 0.0079 (12) | −0.0027 (13) |
N37 | 0.0280 (12) | 0.0251 (14) | 0.0280 (13) | 0.0007 (10) | 0.0069 (10) | −0.0034 (11) |
C37A | 0.0253 (14) | 0.0278 (18) | 0.0230 (15) | 0.0035 (12) | 0.0076 (12) | 0.0012 (13) |
N38 | 0.0338 (13) | 0.0287 (14) | 0.0222 (12) | 0.0012 (11) | 0.0046 (10) | −0.0005 (11) |
C381 | 0.0256 (14) | 0.0383 (19) | 0.0243 (16) | 0.0025 (13) | 0.0068 (12) | 0.0013 (14) |
C382 | 0.0505 (19) | 0.0343 (19) | 0.0303 (17) | 0.0079 (14) | 0.0114 (15) | 0.0033 (14) |
C383 | 0.053 (2) | 0.043 (2) | 0.0336 (18) | 0.0116 (16) | 0.0129 (16) | 0.0077 (16) |
C384 | 0.0375 (17) | 0.055 (2) | 0.0304 (17) | 0.0088 (16) | 0.0055 (14) | 0.0100 (17) |
C385 | 0.0360 (17) | 0.056 (2) | 0.0327 (18) | −0.0087 (15) | 0.0041 (14) | 0.0008 (16) |
C386 | 0.0328 (16) | 0.0413 (19) | 0.0333 (17) | −0.0065 (14) | 0.0067 (14) | 0.0040 (15) |
N39 | 0.0414 (14) | 0.0251 (14) | 0.0318 (14) | −0.0010 (11) | 0.0057 (11) | −0.0020 (12) |
C310 | 0.0335 (16) | 0.0279 (18) | 0.0283 (16) | 0.0017 (13) | 0.0088 (13) | 0.0011 (13) |
C311 | 0.0519 (19) | 0.0260 (18) | 0.0376 (18) | −0.0058 (14) | 0.0019 (15) | −0.0026 (14) |
C31A | 0.0253 (14) | 0.0230 (17) | 0.0257 (15) | −0.0012 (12) | 0.0078 (12) | −0.0020 (12) |
C320 | 0.0221 (14) | 0.0250 (17) | 0.0263 (15) | 0.0006 (12) | 0.0094 (12) | −0.0024 (13) |
C321 | 0.0263 (15) | 0.0230 (16) | 0.0243 (15) | −0.0009 (11) | 0.0079 (12) | 0.0003 (12) |
C322 | 0.0281 (15) | 0.0276 (17) | 0.0245 (15) | 0.0027 (12) | 0.0099 (12) | −0.0020 (12) |
C323 | 0.0228 (14) | 0.0366 (18) | 0.0263 (15) | −0.0006 (12) | 0.0041 (12) | −0.0003 (13) |
C324 | 0.0278 (15) | 0.0318 (17) | 0.0221 (15) | −0.0022 (12) | 0.0042 (12) | −0.0033 (13) |
O324 | 0.0311 (11) | 0.0524 (14) | 0.0274 (11) | 0.0015 (9) | −0.0002 (9) | −0.0115 (10) |
C327 | 0.0286 (16) | 0.068 (2) | 0.0285 (17) | −0.0038 (15) | 0.0058 (13) | −0.0035 (15) |
C325 | 0.0297 (16) | 0.0369 (18) | 0.0320 (16) | 0.0032 (13) | 0.0103 (13) | −0.0073 (14) |
C326 | 0.0249 (14) | 0.0341 (18) | 0.0292 (16) | 0.0016 (12) | 0.0066 (13) | −0.0039 (13) |
C32A | 0.0249 (14) | 0.0251 (17) | 0.0264 (15) | −0.0008 (11) | 0.0073 (12) | −0.0039 (12) |
C32B | 0.0263 (14) | 0.0248 (17) | 0.0313 (16) | −0.0010 (12) | 0.0080 (12) | 0.0002 (13) |
C41 | 0.0306 (16) | 0.0348 (19) | 0.0351 (17) | −0.0034 (13) | 0.0126 (13) | −0.0059 (14) |
C42 | 0.0393 (17) | 0.047 (2) | 0.0327 (17) | −0.0059 (15) | 0.0123 (14) | −0.0088 (16) |
C43 | 0.0410 (18) | 0.042 (2) | 0.045 (2) | −0.0120 (15) | 0.0153 (15) | −0.0182 (16) |
C44 | 0.0394 (17) | 0.0316 (19) | 0.0452 (19) | −0.0068 (13) | 0.0145 (15) | −0.0073 (15) |
C44A | 0.0280 (15) | 0.0333 (19) | 0.0314 (17) | −0.0004 (13) | 0.0066 (13) | −0.0037 (14) |
C45 | 0.0431 (18) | 0.0293 (18) | 0.0359 (18) | −0.0033 (13) | 0.0077 (14) | 0.0005 (14) |
C46 | 0.0322 (16) | 0.0326 (18) | 0.0330 (16) | 0.0028 (13) | 0.0032 (13) | −0.0004 (14) |
C46A | 0.0225 (14) | 0.0307 (18) | 0.0267 (16) | 0.0003 (12) | 0.0067 (12) | −0.0015 (13) |
N47 | 0.0239 (12) | 0.0294 (15) | 0.0276 (13) | 0.0023 (10) | 0.0050 (10) | −0.0002 (11) |
C47A | 0.0251 (14) | 0.0263 (17) | 0.0257 (15) | −0.0017 (12) | 0.0069 (12) | −0.0011 (13) |
N48 | 0.0296 (12) | 0.0288 (14) | 0.0235 (12) | −0.0012 (10) | 0.0060 (10) | −0.0013 (11) |
C481 | 0.0334 (16) | 0.0349 (19) | 0.0215 (15) | −0.0039 (13) | 0.0066 (13) | −0.0029 (14) |
C482 | 0.057 (2) | 0.039 (2) | 0.0282 (17) | −0.0141 (15) | 0.0070 (15) | −0.0018 (15) |
C483 | 0.073 (2) | 0.043 (2) | 0.0343 (19) | −0.0214 (18) | 0.0052 (17) | −0.0106 (16) |
C484 | 0.049 (2) | 0.052 (2) | 0.0294 (18) | −0.0109 (16) | −0.0001 (15) | −0.0068 (17) |
C485 | 0.0397 (18) | 0.052 (2) | 0.0313 (18) | 0.0076 (15) | −0.0016 (14) | −0.0038 (16) |
C486 | 0.0316 (16) | 0.0387 (19) | 0.0312 (17) | 0.0069 (13) | 0.0011 (13) | −0.0070 (14) |
N49 | 0.0365 (13) | 0.0275 (14) | 0.0290 (13) | 0.0014 (11) | 0.0089 (11) | 0.0003 (11) |
C410 | 0.0298 (15) | 0.0296 (18) | 0.0284 (16) | −0.0010 (12) | 0.0097 (13) | −0.0018 (13) |
C411 | 0.0446 (18) | 0.0338 (19) | 0.0351 (17) | 0.0072 (14) | 0.0078 (14) | 0.0050 (14) |
C41A | 0.0243 (14) | 0.0288 (18) | 0.0254 (15) | −0.0007 (12) | 0.0074 (12) | 0.0008 (13) |
C420 | 0.0198 (13) | 0.0305 (17) | 0.0235 (15) | −0.0012 (12) | 0.0065 (11) | −0.0008 (13) |
C421 | 0.0242 (14) | 0.0268 (17) | 0.0237 (15) | −0.0014 (11) | 0.0062 (12) | −0.0016 (12) |
C422 | 0.0283 (15) | 0.0366 (18) | 0.0254 (16) | −0.0014 (12) | 0.0070 (13) | 0.0035 (13) |
C423 | 0.0243 (15) | 0.0401 (19) | 0.0296 (16) | −0.0033 (13) | 0.0024 (13) | 0.0009 (14) |
C424 | 0.0298 (16) | 0.0350 (18) | 0.0235 (15) | 0.0022 (13) | 0.0030 (13) | 0.0028 (13) |
O424 | 0.0344 (11) | 0.0508 (13) | 0.0261 (11) | −0.0051 (9) | 0.0007 (9) | 0.0122 (9) |
C427 | 0.0379 (18) | 0.051 (2) | 0.0339 (17) | −0.0015 (14) | −0.0027 (14) | 0.0118 (15) |
C425 | 0.0342 (16) | 0.0416 (19) | 0.0292 (17) | −0.0071 (13) | 0.0097 (13) | 0.0057 (14) |
C426 | 0.0276 (15) | 0.0384 (18) | 0.0305 (16) | −0.0057 (13) | 0.0056 (13) | −0.0003 (14) |
C42A | 0.0199 (13) | 0.0318 (18) | 0.0248 (15) | −0.0016 (12) | 0.0074 (12) | −0.0050 (13) |
C42B | 0.0231 (14) | 0.0330 (18) | 0.0280 (16) | −0.0038 (12) | 0.0050 (12) | −0.0054 (13) |
C11—C12 | 1.384 (4) | C31—C32 | 1.380 (4) |
C11—C12B | 1.400 (3) | C31—C32B | 1.403 (3) |
C11—H11 | 0.95 | C31—H31 | 0.95 |
C12—C13 | 1.383 (4) | C32—C33 | 1.385 (4) |
C12—H12 | 0.95 | C32—H32 | 0.95 |
C13—C14 | 1.379 (4) | C33—C34 | 1.393 (4) |
C13—H13 | 0.95 | C33—H33 | 0.95 |
C14—C14A | 1.390 (4) | C34—C34A | 1.392 (4) |
C14—H14 | 0.95 | C34—H34 | 0.95 |
C14A—C12B | 1.404 (3) | C34A—C32B | 1.406 (3) |
C14A—C15 | 1.500 (4) | C34A—C35 | 1.499 (3) |
C15—C16 | 1.517 (3) | C35—C36 | 1.521 (3) |
C15—H15A | 0.99 | C35—H35A | 0.99 |
C15—H15B | 0.99 | C35—H35B | 0.99 |
C16—C16A | 1.503 (3) | C36—C36A | 1.500 (3) |
C16—H16A | 0.99 | C36—H36A | 0.99 |
C16—H16B | 0.99 | C36—H36B | 0.99 |
C16A—N17 | 1.338 (3) | C36A—N37 | 1.333 (3) |
C16A—C12A | 1.433 (3) | C36A—C32A | 1.435 (3) |
N17—C17A | 1.343 (3) | N37—C37A | 1.336 (3) |
C17A—N18 | 1.370 (3) | C37A—N38 | 1.376 (3) |
C17A—C11A | 1.398 (3) | C37A—C31A | 1.397 (3) |
N18—N19 | 1.381 (3) | N38—N39 | 1.387 (3) |
N18—C181 | 1.421 (3) | N38—C381 | 1.424 (3) |
C181—C186 | 1.380 (4) | C381—C386 | 1.380 (3) |
C181—C182 | 1.383 (4) | C381—C382 | 1.389 (3) |
C182—C183 | 1.392 (4) | C382—C383 | 1.382 (3) |
C182—H182 | 0.95 | C382—H382 | 0.95 |
C183—C184 | 1.377 (4) | C383—C384 | 1.376 (4) |
C183—H183 | 0.95 | C383—H383 | 0.95 |
C184—C185 | 1.372 (4) | C384—C385 | 1.372 (4) |
C184—H184 | 0.95 | C384—H384 | 0.95 |
C185—C186 | 1.388 (4) | C385—C386 | 1.391 (3) |
C185—H185 | 0.95 | C385—H385 | 0.95 |
C186—H186 | 0.95 | C386—H386 | 0.95 |
N19—C110 | 1.321 (3) | N39—C310 | 1.318 (3) |
C110—C11A | 1.429 (3) | C310—C31A | 1.430 (3) |
C110—C111 | 1.499 (3) | C310—C311 | 1.495 (3) |
C111—H11A | 0.98 | C311—H31A | 0.98 |
C111—H11B | 0.98 | C311—H31B | 0.98 |
C111—H11C | 0.98 | C311—H31C | 0.98 |
C11A—C120 | 1.407 (3) | C31A—C320 | 1.407 (3) |
C120—C12A | 1.401 (3) | C320—C32A | 1.398 (3) |
C120—C121 | 1.489 (3) | C320—C321 | 1.501 (3) |
C121—C122 | 1.382 (3) | C321—C322 | 1.384 (3) |
C121—C126 | 1.398 (3) | C321—C326 | 1.401 (3) |
C122—C123 | 1.390 (3) | C322—C323 | 1.392 (3) |
C122—H122 | 0.95 | C322—H322 | 0.95 |
C123—C124 | 1.391 (3) | C323—C324 | 1.384 (3) |
C123—H123 | 0.95 | C323—H323 | 0.95 |
C124—O124 | 1.365 (3) | C324—O324 | 1.369 (3) |
C124—C125 | 1.386 (3) | C324—C325 | 1.381 (3) |
O124—C127 | 1.425 (3) | O324—C327 | 1.414 (3) |
C127—H12A | 0.98 | C327—H32A | 0.98 |
C127—H12B | 0.98 | C327—H32B | 0.98 |
C127—H12C | 0.98 | C327—H32C | 0.98 |
C125—C126 | 1.373 (3) | C325—C326 | 1.380 (3) |
C125—H125 | 0.95 | C325—H325 | 0.95 |
C126—H126 | 0.95 | C326—H326 | 0.95 |
C12A—C12B | 1.492 (3) | C32A—C32B | 1.491 (3) |
C21—C22 | 1.372 (3) | C41—C42 | 1.381 (3) |
C21—C22B | 1.403 (3) | C41—C42B | 1.403 (3) |
C21—H21 | 0.95 | C41—H41 | 0.95 |
C22—C23 | 1.381 (4) | C42—C43 | 1.378 (4) |
C22—H22 | 0.95 | C42—H42 | 0.95 |
C23—C24 | 1.386 (3) | C43—C44 | 1.382 (4) |
C23—H23 | 0.95 | C43—H43 | 0.95 |
C24—C24A | 1.397 (3) | C44—C44A | 1.388 (4) |
C24—H24 | 0.95 | C44—H44 | 0.95 |
C24A—C22B | 1.407 (3) | C44A—C42B | 1.408 (4) |
C24A—C25 | 1.505 (3) | C44A—C45 | 1.502 (3) |
C25—C26 | 1.520 (3) | C45—C46 | 1.522 (3) |
C25—H25A | 0.99 | C45—H45A | 0.99 |
C25—H25B | 0.99 | C45—H45B | 0.99 |
C26—C26A | 1.495 (3) | C46—C46A | 1.498 (3) |
C26—H26A | 0.99 | C46—H46A | 0.99 |
C26—H26B | 0.99 | C46—H46B | 0.99 |
C26A—N27 | 1.337 (3) | C46A—N47 | 1.338 (3) |
C26A—C22A | 1.432 (3) | C46A—C42A | 1.426 (3) |
N27—C27A | 1.342 (3) | N47—C47A | 1.342 (3) |
C27A—N28 | 1.370 (3) | C47A—N48 | 1.376 (3) |
C27A—C21A | 1.401 (3) | C47A—C41A | 1.392 (3) |
N28—N29 | 1.376 (3) | N48—N49 | 1.387 (3) |
N28—C281 | 1.424 (3) | N48—C481 | 1.419 (3) |
C281—C286 | 1.385 (4) | C481—C486 | 1.378 (3) |
C281—C282 | 1.387 (3) | C481—C482 | 1.391 (4) |
C282—C283 | 1.381 (4) | C482—C483 | 1.386 (4) |
C282—H282 | 0.95 | C482—H482 | 0.95 |
C283—C284 | 1.384 (4) | C483—C484 | 1.378 (4) |
C283—H283 | 0.95 | C483—H483 | 0.95 |
C284—C285 | 1.380 (4) | C484—C485 | 1.378 (4) |
C284—H284 | 0.95 | C484—H484 | 0.95 |
C285—C286 | 1.388 (3) | C485—C486 | 1.390 (3) |
C285—H285 | 0.95 | C485—H485 | 0.95 |
C286—H286 | 0.95 | C486—H486 | 0.95 |
N29—C210 | 1.316 (3) | N49—C410 | 1.316 (3) |
C210—C21A | 1.433 (3) | C410—C41A | 1.437 (3) |
C210—C211 | 1.502 (4) | C410—C411 | 1.492 (3) |
C211—H21A | 0.98 | C411—H41A | 0.98 |
C211—H21B | 0.98 | C411—H41B | 0.98 |
C211—H21C | 0.98 | C411—H41C | 0.98 |
C21A—C220 | 1.416 (3) | C41A—C420 | 1.411 (3) |
C220—C22A | 1.405 (3) | C420—C42A | 1.402 (3) |
C220—C221 | 1.492 (3) | C420—C421 | 1.489 (3) |
C221—C226 | 1.390 (3) | C421—C422 | 1.383 (3) |
C221—C222 | 1.391 (3) | C421—C426 | 1.392 (3) |
C222—C223 | 1.391 (3) | C422—C423 | 1.391 (3) |
C222—H222 | 0.95 | C422—H422 | 0.95 |
C223—C224 | 1.384 (3) | C423—C424 | 1.388 (3) |
C223—H223 | 0.95 | C423—H423 | 0.95 |
C224—O224 | 1.374 (3) | C424—O424 | 1.369 (3) |
C224—C225 | 1.388 (3) | C424—C425 | 1.388 (3) |
O224—C227 | 1.420 (3) | O424—C427 | 1.429 (3) |
C227—H27A | 0.98 | C427—H42A | 0.98 |
C227—H27B | 0.98 | C427—H42B | 0.98 |
C227—H27C | 0.98 | C427—H42C | 0.98 |
C225—C226 | 1.375 (3) | C425—C426 | 1.376 (3) |
C225—H225 | 0.95 | C425—H425 | 0.95 |
C226—H226 | 0.95 | C426—H426 | 0.95 |
C22A—C22B | 1.493 (3) | C42A—C42B | 1.492 (3) |
C12—C11—C12B | 121.0 (3) | C32—C31—C32B | 121.4 (3) |
C12—C11—H11 | 119.5 | C32—C31—H31 | 119.3 |
C12B—C11—H11 | 119.5 | C32B—C31—H31 | 119.3 |
C13—C12—C11 | 120.0 (3) | C31—C32—C33 | 120.3 (3) |
C13—C12—H12 | 120.0 | C31—C32—H32 | 119.9 |
C11—C12—H12 | 120.0 | C33—C32—H32 | 119.9 |
C14—C13—C12 | 119.9 (3) | C32—C33—C34 | 119.4 (3) |
C14—C13—H13 | 120.0 | C32—C33—H33 | 120.3 |
C12—C13—H13 | 120.0 | C34—C33—H33 | 120.3 |
C13—C14—C14A | 120.7 (3) | C34A—C34—C33 | 120.8 (3) |
C13—C14—H14 | 119.6 | C34A—C34—H34 | 119.6 |
C14A—C14—H14 | 119.6 | C33—C34—H34 | 119.6 |
C14—C14A—C12B | 120.0 (3) | C34—C34A—C32B | 120.1 (3) |
C14—C14A—C15 | 121.9 (3) | C34—C34A—C35 | 121.5 (3) |
C12B—C14A—C15 | 118.0 (2) | C32B—C34A—C35 | 118.3 (2) |
C14A—C15—C16 | 108.9 (2) | C34A—C35—C36 | 109.1 (2) |
C14A—C15—H15A | 109.9 | C34A—C35—H35A | 109.9 |
C16—C15—H15A | 109.9 | C36—C35—H35A | 109.9 |
C14A—C15—H15B | 109.9 | C34A—C35—H35B | 109.9 |
C16—C15—H15B | 109.9 | C36—C35—H35B | 109.9 |
H15A—C15—H15B | 108.3 | H35A—C35—H35B | 108.3 |
C16A—C16—C15 | 109.0 (2) | C36A—C36—C35 | 109.2 (2) |
C16A—C16—H16A | 109.9 | C36A—C36—H36A | 109.8 |
C15—C16—H16A | 109.9 | C35—C36—H36A | 109.8 |
C16A—C16—H16B | 109.9 | C36A—C36—H36B | 109.8 |
C15—C16—H16B | 109.9 | C35—C36—H36B | 109.8 |
H16A—C16—H16B | 108.3 | H36A—C36—H36B | 108.3 |
N17—C16A—C12A | 125.1 (2) | N37—C36A—C32A | 125.5 (2) |
N17—C16A—C16 | 115.8 (2) | N37—C36A—C36 | 115.9 (2) |
C12A—C16A—C16 | 119.1 (2) | C32A—C36A—C36 | 118.6 (2) |
C16A—N17—C17A | 114.0 (2) | C36A—N37—C37A | 114.2 (2) |
N17—C17A—N18 | 125.8 (2) | N37—C37A—N38 | 126.1 (2) |
N17—C17A—C11A | 126.5 (2) | N37—C37A—C31A | 126.3 (2) |
N18—C17A—C11A | 107.6 (2) | N38—C37A—C31A | 107.4 (2) |
C17A—N18—N19 | 109.9 (2) | C37A—N38—N39 | 109.8 (2) |
C17A—N18—C181 | 131.0 (2) | C37A—N38—C381 | 131.8 (2) |
N19—N18—C181 | 119.1 (2) | N39—N38—C381 | 118.2 (2) |
C186—C181—C182 | 120.2 (3) | C386—C381—C382 | 120.0 (2) |
C186—C181—N18 | 120.7 (3) | C386—C381—N38 | 121.1 (2) |
C182—C181—N18 | 119.0 (3) | C382—C381—N38 | 118.9 (2) |
C181—C182—C183 | 119.2 (3) | C383—C382—C381 | 119.7 (3) |
C181—C182—H182 | 120.4 | C383—C382—H382 | 120.1 |
C183—C182—H182 | 120.4 | C381—C382—H382 | 120.1 |
C184—C183—C182 | 120.7 (3) | C384—C383—C382 | 120.5 (3) |
C184—C183—H183 | 119.7 | C384—C383—H383 | 119.7 |
C182—C183—H183 | 119.7 | C382—C383—H383 | 119.7 |
C185—C184—C183 | 119.5 (3) | C385—C384—C383 | 119.6 (3) |
C185—C184—H184 | 120.2 | C385—C384—H384 | 120.2 |
C183—C184—H184 | 120.2 | C383—C384—H384 | 120.2 |
C184—C185—C186 | 120.6 (3) | C384—C385—C386 | 120.8 (3) |
C184—C185—H185 | 119.7 | C384—C385—H385 | 119.6 |
C186—C185—H185 | 119.7 | C386—C385—H385 | 119.6 |
C181—C186—C185 | 119.6 (3) | C381—C386—C385 | 119.4 (3) |
C181—C186—H186 | 120.2 | C381—C386—H386 | 120.3 |
C185—C186—H186 | 120.2 | C385—C386—H386 | 120.3 |
C110—N19—N18 | 107.1 (2) | C310—N39—N38 | 107.1 (2) |
N19—C110—C11A | 110.8 (2) | N39—C310—C31A | 110.9 (2) |
N19—C110—C111 | 119.4 (2) | N39—C310—C311 | 119.2 (2) |
C11A—C110—C111 | 129.8 (2) | C31A—C310—C311 | 129.8 (2) |
C110—C111—H11A | 109.5 | C310—C311—H31A | 109.5 |
C110—C111—H11B | 109.5 | C310—C311—H31B | 109.5 |
H11A—C111—H11B | 109.5 | H31A—C311—H31B | 109.5 |
C110—C111—H11C | 109.5 | C310—C311—H31C | 109.5 |
H11A—C111—H11C | 109.5 | H31A—C311—H31C | 109.5 |
H11B—C111—H11C | 109.5 | H31B—C311—H31C | 109.5 |
C17A—C11A—C120 | 118.9 (2) | C37A—C31A—C320 | 119.0 (2) |
C17A—C11A—C110 | 104.6 (2) | C37A—C31A—C310 | 104.8 (2) |
C120—C11A—C110 | 136.5 (2) | C320—C31A—C310 | 136.0 (2) |
C12A—C120—C11A | 116.6 (2) | C32A—C320—C31A | 116.7 (2) |
C12A—C120—C121 | 125.5 (2) | C32A—C320—C321 | 125.6 (2) |
C11A—C120—C121 | 117.9 (2) | C31A—C320—C321 | 117.6 (2) |
C122—C121—C126 | 118.1 (2) | C322—C321—C326 | 118.0 (2) |
C122—C121—C120 | 123.0 (2) | C322—C321—C320 | 122.4 (2) |
C126—C121—C120 | 118.9 (2) | C326—C321—C320 | 119.5 (2) |
C121—C122—C123 | 121.4 (2) | C321—C322—C323 | 121.3 (2) |
C121—C122—H122 | 119.3 | C321—C322—H322 | 119.3 |
C123—C122—H122 | 119.3 | C323—C322—H322 | 119.3 |
C122—C123—C124 | 119.7 (2) | C324—C323—C322 | 119.7 (2) |
C122—C123—H123 | 120.2 | C324—C323—H323 | 120.2 |
C124—C123—H123 | 120.2 | C322—C323—H323 | 120.2 |
O124—C124—C125 | 115.6 (2) | O324—C324—C325 | 115.5 (2) |
O124—C124—C123 | 125.2 (2) | O324—C324—C323 | 124.8 (2) |
C125—C124—C123 | 119.2 (2) | C325—C324—C323 | 119.7 (2) |
C124—O124—C127 | 118.3 (2) | C324—O324—C327 | 118.4 (2) |
O124—C127—H12A | 109.5 | O324—C327—H32A | 109.5 |
O124—C127—H12B | 109.5 | O324—C327—H32B | 109.5 |
H12A—C127—H12B | 109.5 | H32A—C327—H32B | 109.5 |
O124—C127—H12C | 109.5 | O324—C327—H32C | 109.5 |
H12A—C127—H12C | 109.5 | H32A—C327—H32C | 109.5 |
H12B—C127—H12C | 109.5 | H32B—C327—H32C | 109.5 |
C126—C125—C124 | 120.7 (2) | C326—C325—C324 | 120.5 (2) |
C126—C125—H125 | 119.7 | C326—C325—H325 | 119.8 |
C124—C125—H125 | 119.7 | C324—C325—H325 | 119.8 |
C125—C126—C121 | 120.9 (2) | C325—C326—C321 | 120.8 (2) |
C125—C126—H126 | 119.5 | C325—C326—H326 | 119.6 |
C121—C126—H126 | 119.5 | C321—C326—H326 | 119.6 |
C120—C12A—C16A | 118.7 (2) | C320—C32A—C36A | 118.2 (2) |
C120—C12A—C12B | 124.8 (2) | C320—C32A—C32B | 124.9 (2) |
C16A—C12A—C12B | 116.5 (2) | C36A—C32A—C32B | 116.9 (2) |
C11—C12B—C14A | 118.3 (2) | C31—C32B—C34A | 118.0 (2) |
C11—C12B—C12A | 122.8 (2) | C31—C32B—C32A | 123.4 (2) |
C14A—C12B—C12A | 118.8 (2) | C34A—C32B—C32A | 118.5 (2) |
C22—C21—C22B | 121.2 (3) | C42—C41—C42B | 121.0 (3) |
C22—C21—H21 | 119.4 | C42—C41—H41 | 119.5 |
C22B—C21—H21 | 119.4 | C42B—C41—H41 | 119.5 |
C21—C22—C23 | 120.6 (3) | C43—C42—C41 | 120.4 (3) |
C21—C22—H22 | 119.7 | C43—C42—H42 | 119.8 |
C23—C22—H22 | 119.7 | C41—C42—H42 | 119.8 |
C22—C23—C24 | 119.5 (3) | C42—C43—C44 | 119.7 (3) |
C22—C23—H23 | 120.3 | C42—C43—H43 | 120.1 |
C24—C23—H23 | 120.3 | C44—C43—H43 | 120.1 |
C23—C24—C24A | 120.7 (3) | C43—C44—C44A | 120.9 (3) |
C23—C24—H24 | 119.6 | C43—C44—H44 | 119.6 |
C24A—C24—H24 | 119.6 | C44A—C44—H44 | 119.6 |
C24—C24A—C22B | 119.8 (2) | C44—C44A—C42B | 119.9 (3) |
C24—C24A—C25 | 121.5 (2) | C44—C44A—C45 | 121.4 (3) |
C22B—C24A—C25 | 118.7 (2) | C42B—C44A—C45 | 118.6 (2) |
C24A—C25—C26 | 108.7 (2) | C44A—C45—C46 | 108.9 (2) |
C24A—C25—H25A | 109.9 | C44A—C45—H45A | 109.9 |
C26—C25—H25A | 109.9 | C46—C45—H45A | 109.9 |
C24A—C25—H25B | 109.9 | C44A—C45—H45B | 109.9 |
C26—C25—H25B | 109.9 | C46—C45—H45B | 109.9 |
H25A—C25—H25B | 108.3 | H45A—C45—H45B | 108.3 |
C26A—C26—C25 | 109.7 (2) | C46A—C46—C45 | 109.7 (2) |
C26A—C26—H26A | 109.7 | C46A—C46—H46A | 109.7 |
C25—C26—H26A | 109.7 | C45—C46—H46A | 109.7 |
C26A—C26—H26B | 109.7 | C46A—C46—H46B | 109.7 |
C25—C26—H26B | 109.7 | C45—C46—H46B | 109.7 |
H26A—C26—H26B | 108.2 | H46A—C46—H46B | 108.2 |
N27—C26A—C22A | 124.8 (2) | N47—C46A—C42A | 125.2 (2) |
N27—C26A—C26 | 115.9 (2) | N47—C46A—C46 | 115.4 (2) |
C22A—C26A—C26 | 119.3 (2) | C42A—C46A—C46 | 119.4 (2) |
C26A—N27—C27A | 114.1 (2) | C46A—N47—C47A | 114.2 (2) |
N27—C27A—N28 | 125.5 (2) | N47—C47A—N48 | 126.2 (2) |
N27—C27A—C21A | 127.1 (2) | N47—C47A—C41A | 126.5 (2) |
N28—C27A—C21A | 107.3 (2) | N48—C47A—C41A | 107.2 (2) |
C27A—N28—N29 | 110.0 (2) | C47A—N48—N49 | 109.90 (19) |
C27A—N28—C281 | 131.0 (2) | C47A—N48—C481 | 131.4 (2) |
N29—N28—C281 | 118.9 (2) | N49—N48—C481 | 118.7 (2) |
C286—C281—C282 | 120.0 (2) | C486—C481—C482 | 120.0 (2) |
C286—C281—N28 | 121.0 (2) | C486—C481—N48 | 121.6 (2) |
C282—C281—N28 | 118.9 (2) | C482—C481—N48 | 118.3 (2) |
C283—C282—C281 | 119.8 (3) | C483—C482—C481 | 119.2 (3) |
C283—C282—H282 | 120.1 | C483—C482—H482 | 120.4 |
C281—C282—H282 | 120.1 | C481—C482—H482 | 120.4 |
C282—C283—C284 | 120.4 (3) | C484—C483—C482 | 121.1 (3) |
C282—C283—H283 | 119.8 | C484—C483—H483 | 119.5 |
C284—C283—H283 | 119.8 | C482—C483—H483 | 119.5 |
C285—C284—C283 | 119.7 (3) | C483—C484—C485 | 119.2 (3) |
C285—C284—H284 | 120.2 | C483—C484—H484 | 120.4 |
C283—C284—H284 | 120.2 | C485—C484—H484 | 120.4 |
C284—C285—C286 | 120.4 (3) | C484—C485—C486 | 120.6 (3) |
C284—C285—H285 | 119.8 | C484—C485—H485 | 119.7 |
C286—C285—H285 | 119.8 | C486—C485—H485 | 119.7 |
C281—C286—C285 | 119.7 (3) | C481—C486—C485 | 119.8 (3) |
C281—C286—H286 | 120.2 | C481—C486—H486 | 120.1 |
C285—C286—H286 | 120.2 | C485—C486—H486 | 120.1 |
C210—N29—N28 | 107.6 (2) | C410—N49—N48 | 107.3 (2) |
N29—C210—C21A | 110.4 (2) | N49—C410—C41A | 110.4 (2) |
N29—C210—C211 | 118.9 (2) | N49—C410—C411 | 118.7 (2) |
C21A—C210—C211 | 130.7 (2) | C41A—C410—C411 | 130.9 (2) |
C210—C211—H21A | 109.5 | C410—C411—H41A | 109.5 |
C210—C211—H21B | 109.5 | C410—C411—H41B | 109.5 |
H21A—C211—H21B | 109.5 | H41A—C411—H41B | 109.5 |
C210—C211—H21C | 109.5 | C410—C411—H41C | 109.5 |
H21A—C211—H21C | 109.5 | H41A—C411—H41C | 109.5 |
H21B—C211—H21C | 109.5 | H41B—C411—H41C | 109.5 |
C27A—C21A—C220 | 118.3 (2) | C47A—C41A—C420 | 118.6 (2) |
C27A—C21A—C210 | 104.7 (2) | C47A—C41A—C410 | 105.2 (2) |
C220—C21A—C210 | 136.9 (2) | C420—C41A—C410 | 136.1 (2) |
C22A—C220—C21A | 116.3 (2) | C42A—C420—C41A | 116.9 (2) |
C22A—C220—C221 | 124.2 (2) | C42A—C420—C421 | 125.5 (2) |
C21A—C220—C221 | 119.5 (2) | C41A—C420—C421 | 117.6 (2) |
C226—C221—C222 | 118.2 (2) | C422—C421—C426 | 118.2 (2) |
C226—C221—C220 | 120.6 (2) | C422—C421—C420 | 122.0 (2) |
C222—C221—C220 | 121.2 (2) | C426—C421—C420 | 119.8 (2) |
C223—C222—C221 | 121.1 (2) | C421—C422—C423 | 121.2 (2) |
C223—C222—H222 | 119.5 | C421—C422—H422 | 119.4 |
C221—C222—H222 | 119.5 | C423—C422—H422 | 119.4 |
C224—C223—C222 | 119.5 (2) | C424—C423—C422 | 119.6 (2) |
C224—C223—H223 | 120.2 | C424—C423—H423 | 120.2 |
C222—C223—H223 | 120.2 | C422—C423—H423 | 120.2 |
O224—C224—C223 | 125.0 (2) | O424—C424—C425 | 115.4 (2) |
O224—C224—C225 | 115.0 (2) | O424—C424—C423 | 124.9 (2) |
C223—C224—C225 | 120.0 (2) | C425—C424—C423 | 119.7 (2) |
C224—O224—C227 | 117.6 (2) | C424—O424—C427 | 117.6 (2) |
O224—C227—H27A | 109.5 | O424—C427—H42A | 109.5 |
O224—C227—H27B | 109.5 | O424—C427—H42B | 109.5 |
H27A—C227—H27B | 109.5 | H42A—C427—H42B | 109.5 |
O224—C227—H27C | 109.5 | O424—C427—H42C | 109.5 |
H27A—C227—H27C | 109.5 | H42A—C427—H42C | 109.5 |
H27B—C227—H27C | 109.5 | H42B—C427—H42C | 109.5 |
C226—C225—C224 | 119.9 (3) | C426—C425—C424 | 119.9 (3) |
C226—C225—H225 | 120.0 | C426—C425—H425 | 120.0 |
C224—C225—H225 | 120.0 | C424—C425—H425 | 120.0 |
C225—C226—C221 | 121.3 (2) | C425—C426—C421 | 121.4 (2) |
C225—C226—H226 | 119.3 | C425—C426—H426 | 119.3 |
C221—C226—H226 | 119.3 | C421—C426—H426 | 119.3 |
C220—C22A—C26A | 119.4 (2) | C420—C42A—C46A | 118.5 (2) |
C220—C22A—C22B | 124.5 (2) | C420—C42A—C42B | 124.9 (2) |
C26A—C22A—C22B | 116.1 (2) | C46A—C42A—C42B | 116.6 (2) |
C21—C22B—C24A | 118.1 (2) | C41—C42B—C44A | 118.1 (2) |
C21—C22B—C22A | 122.8 (2) | C41—C42B—C42A | 123.0 (2) |
C24A—C22B—C22A | 119.0 (2) | C44A—C42B—C42A | 118.9 (2) |
C12B—C11—C12—C13 | 0.3 (4) | C32B—C31—C32—C33 | −0.2 (4) |
C11—C12—C13—C14 | 0.8 (4) | C31—C32—C33—C34 | 1.2 (4) |
C12—C13—C14—C14A | −0.5 (4) | C32—C33—C34—C34A | −0.9 (4) |
C13—C14—C14A—C12B | −1.0 (4) | C33—C34—C34A—C32B | −0.4 (4) |
C13—C14—C14A—C15 | 176.5 (3) | C33—C34—C34A—C35 | 176.4 (3) |
C14—C14A—C15—C16 | −134.8 (3) | C34—C34A—C35—C36 | −135.8 (3) |
C12B—C14A—C15—C16 | 42.7 (3) | C32B—C34A—C35—C36 | 41.1 (3) |
C14A—C15—C16—C16A | −59.6 (3) | C34A—C35—C36—C36A | −59.5 (3) |
C15—C16—C16A—N17 | −142.4 (2) | C35—C36—C36A—N37 | −140.8 (2) |
C15—C16—C16A—C12A | 36.6 (3) | C35—C36—C36A—C32A | 37.7 (3) |
C12A—C16A—N17—C17A | −1.7 (4) | C32A—C36A—N37—C37A | −1.5 (4) |
C16—C16A—N17—C17A | 177.3 (2) | C36—C36A—N37—C37A | 176.9 (2) |
C16A—N17—C17A—N18 | −179.4 (2) | C36A—N37—C37A—N38 | −176.1 (2) |
C16A—N17—C17A—C11A | −1.6 (4) | C36A—N37—C37A—C31A | −2.0 (4) |
N17—C17A—N18—N19 | 175.8 (2) | N37—C37A—N38—N39 | 172.5 (2) |
C11A—C17A—N18—N19 | −2.3 (3) | C31A—C37A—N38—N39 | −2.6 (3) |
N17—C17A—N18—C181 | −2.8 (4) | N37—C37A—N38—C381 | −2.2 (4) |
C11A—C17A—N18—C181 | 179.0 (2) | C31A—C37A—N38—C381 | −177.3 (2) |
C17A—N18—C181—C186 | 26.4 (4) | C37A—N38—C381—C386 | −10.2 (4) |
N19—N18—C181—C186 | −152.1 (2) | N39—N38—C381—C386 | 175.4 (2) |
C17A—N18—C181—C182 | −153.5 (3) | C37A—N38—C381—C382 | 169.6 (2) |
N19—N18—C181—C182 | 28.0 (4) | N39—N38—C381—C382 | −4.7 (3) |
C186—C181—C182—C183 | 2.1 (4) | C386—C381—C382—C383 | −1.0 (4) |
N18—C181—C182—C183 | −178.1 (3) | N38—C381—C382—C383 | 179.2 (2) |
C181—C182—C183—C184 | −0.7 (5) | C381—C382—C383—C384 | 0.7 (4) |
C182—C183—C184—C185 | −0.7 (5) | C382—C383—C384—C385 | −0.1 (4) |
C183—C184—C185—C186 | 0.7 (5) | C383—C384—C385—C386 | −0.2 (4) |
C182—C181—C186—C185 | −2.0 (4) | C382—C381—C386—C385 | 0.7 (4) |
N18—C181—C186—C185 | 178.1 (2) | N38—C381—C386—C385 | −179.5 (2) |
C184—C185—C186—C181 | 0.6 (4) | C384—C385—C386—C381 | 0.0 (4) |
C17A—N18—N19—C110 | 1.2 (3) | C37A—N38—N39—C310 | 1.3 (3) |
C181—N18—N19—C110 | 180.0 (2) | C381—N38—N39—C310 | 176.8 (2) |
N18—N19—C110—C11A | 0.4 (3) | N38—N39—C310—C31A | 0.5 (3) |
N18—N19—C110—C111 | −176.8 (2) | N38—N39—C310—C311 | −176.4 (2) |
N17—C17A—C11A—C120 | 2.7 (4) | N37—C37A—C31A—C320 | 3.5 (4) |
N18—C17A—C11A—C120 | −179.2 (2) | N38—C37A—C31A—C320 | 178.6 (2) |
N17—C17A—C11A—C110 | −175.6 (2) | N37—C37A—C31A—C310 | −172.3 (2) |
N18—C17A—C11A—C110 | 2.5 (3) | N38—C37A—C31A—C310 | 2.7 (3) |
N19—C110—C11A—C17A | −1.8 (3) | N39—C310—C31A—C37A | −2.0 (3) |
C111—C110—C11A—C17A | 175.0 (3) | C311—C310—C31A—C37A | 174.4 (3) |
N19—C110—C11A—C120 | −179.7 (3) | N39—C310—C31A—C320 | −176.8 (3) |
C111—C110—C11A—C120 | −2.9 (5) | C311—C310—C31A—C320 | −0.4 (5) |
C17A—C11A—C120—C12A | −0.5 (3) | C37A—C31A—C320—C32A | −1.5 (3) |
C110—C11A—C120—C12A | 177.2 (3) | C310—C31A—C320—C32A | 172.7 (3) |
C17A—C11A—C120—C121 | 178.2 (2) | C37A—C31A—C320—C321 | 179.6 (2) |
C110—C11A—C120—C121 | −4.1 (4) | C310—C31A—C320—C321 | −6.1 (4) |
C12A—C120—C121—C122 | −67.0 (3) | C32A—C320—C321—C322 | −66.9 (3) |
C11A—C120—C121—C122 | 114.5 (3) | C31A—C320—C321—C322 | 111.9 (3) |
C12A—C120—C121—C126 | 115.1 (3) | C32A—C320—C321—C326 | 116.5 (3) |
C11A—C120—C121—C126 | −63.5 (3) | C31A—C320—C321—C326 | −64.8 (3) |
C126—C121—C122—C123 | 0.4 (4) | C326—C321—C322—C323 | −0.4 (4) |
C120—C121—C122—C123 | −177.6 (2) | C320—C321—C322—C323 | −177.1 (2) |
C121—C122—C123—C124 | −0.3 (4) | C321—C322—C323—C324 | 0.4 (4) |
C122—C123—C124—O124 | 179.5 (2) | C322—C323—C324—O324 | 179.1 (2) |
C122—C123—C124—C125 | −0.9 (4) | C322—C323—C324—C325 | −0.2 (4) |
C125—C124—O124—C127 | 176.6 (2) | C325—C324—O324—C327 | −171.2 (2) |
C123—C124—O124—C127 | −3.8 (4) | C323—C324—O324—C327 | 9.4 (4) |
O124—C124—C125—C126 | −178.3 (2) | O324—C324—C325—C326 | −179.3 (2) |
C123—C124—C125—C126 | 2.0 (4) | C323—C324—C325—C326 | 0.1 (4) |
C124—C125—C126—C121 | −1.9 (4) | C324—C325—C326—C321 | −0.2 (4) |
C122—C121—C126—C125 | 0.7 (4) | C322—C321—C326—C325 | 0.3 (4) |
C120—C121—C126—C125 | 178.8 (2) | C320—C321—C326—C325 | 177.1 (2) |
C11A—C120—C12A—C16A | −2.4 (3) | C31A—C320—C32A—C36A | −1.4 (3) |
C121—C120—C12A—C16A | 179.0 (2) | C321—C320—C32A—C36A | 177.3 (2) |
C11A—C120—C12A—C12B | 176.2 (2) | C31A—C320—C32A—C32B | 178.2 (2) |
C121—C120—C12A—C12B | −2.4 (4) | C321—C320—C32A—C32B | −3.0 (4) |
N17—C16A—C12A—C120 | 3.8 (4) | N37—C36A—C32A—C320 | 3.2 (4) |
C16—C16A—C12A—C120 | −175.2 (2) | C36—C36A—C32A—C320 | −175.1 (2) |
N17—C16A—C12A—C12B | −175.0 (2) | N37—C36A—C32A—C32B | −176.5 (2) |
C16—C16A—C12A—C12B | 6.1 (3) | C36—C36A—C32A—C32B | 5.2 (3) |
C12—C11—C12B—C14A | −1.7 (4) | C32—C31—C32B—C34A | −1.2 (4) |
C12—C11—C12B—C12A | −177.7 (2) | C32—C31—C32B—C32A | −178.8 (2) |
C14—C14A—C12B—C11 | 2.0 (4) | C34—C34A—C32B—C31 | 1.5 (4) |
C15—C14A—C12B—C11 | −175.5 (2) | C35—C34A—C32B—C31 | −175.5 (2) |
C14—C14A—C12B—C12A | 178.2 (2) | C34—C34A—C32B—C32A | 179.2 (2) |
C15—C14A—C12B—C12A | 0.6 (3) | C35—C34A—C32B—C32A | 2.2 (3) |
C120—C12A—C12B—C11 | −29.1 (4) | C320—C32A—C32B—C31 | −29.1 (4) |
C16A—C12A—C12B—C11 | 149.5 (2) | C36A—C32A—C32B—C31 | 150.6 (2) |
C120—C12A—C12B—C14A | 154.9 (2) | C320—C32A—C32B—C34A | 153.4 (2) |
C16A—C12A—C12B—C14A | −26.5 (3) | C36A—C32A—C32B—C34A | −26.9 (3) |
C22B—C21—C22—C23 | 0.6 (4) | C42B—C41—C42—C43 | 1.1 (4) |
C21—C22—C23—C24 | 0.6 (4) | C41—C42—C43—C44 | 0.7 (4) |
C22—C23—C24—C24A | −0.3 (4) | C42—C43—C44—C44A | −1.2 (4) |
C23—C24—C24A—C22B | −1.2 (4) | C43—C44—C44A—C42B | 0.0 (4) |
C23—C24—C24A—C25 | 175.9 (2) | C43—C44—C44A—C45 | 178.8 (3) |
C24—C24A—C25—C26 | −138.0 (2) | C44—C44A—C45—C46 | −138.5 (3) |
C22B—C24A—C25—C26 | 39.2 (3) | C42B—C44A—C45—C46 | 40.3 (3) |
C24A—C25—C26—C26A | −58.5 (3) | C44A—C45—C46—C46A | −57.9 (3) |
C25—C26—C26A—N27 | −139.5 (2) | C45—C46—C46A—N47 | −141.9 (2) |
C25—C26—C26A—C22A | 38.8 (3) | C45—C46—C46A—C42A | 37.2 (3) |
C22A—C26A—N27—C27A | 0.6 (4) | C42A—C46A—N47—C47A | −2.5 (4) |
C26—C26A—N27—C27A | 178.8 (2) | C46—C46A—N47—C47A | 176.5 (2) |
C26A—N27—C27A—N28 | −177.6 (2) | C46A—N47—C47A—N48 | −176.7 (2) |
C26A—N27—C27A—C21A | −1.3 (4) | C46A—N47—C47A—C41A | −1.0 (4) |
N27—C27A—N28—N29 | 176.1 (2) | N47—C47A—N48—N49 | 173.9 (2) |
C21A—C27A—N28—N29 | −0.9 (3) | C41A—C47A—N48—N49 | −2.5 (3) |
N27—C27A—N28—C281 | 0.1 (4) | N47—C47A—N48—C481 | −8.3 (4) |
C21A—C27A—N28—C281 | −176.9 (2) | C41A—C47A—N48—C481 | 175.2 (2) |
C27A—N28—C281—C286 | −18.9 (4) | C47A—N48—C481—C486 | 9.2 (4) |
N29—N28—C281—C286 | 165.4 (2) | N49—N48—C481—C486 | −173.2 (2) |
C27A—N28—C281—C282 | 162.6 (3) | C47A—N48—C481—C482 | −171.3 (2) |
N29—N28—C281—C282 | −13.1 (3) | N49—N48—C481—C482 | 6.3 (3) |
C286—C281—C282—C283 | −0.8 (4) | C486—C481—C482—C483 | 0.7 (4) |
N28—C281—C282—C283 | 177.7 (2) | N48—C481—C482—C483 | −178.8 (3) |
C281—C282—C283—C284 | 0.3 (4) | C481—C482—C483—C484 | −1.0 (5) |
C282—C283—C284—C285 | 0.3 (4) | C482—C483—C484—C485 | 0.6 (5) |
C283—C284—C285—C286 | −0.5 (4) | C483—C484—C485—C486 | 0.1 (5) |
C282—C281—C286—C285 | 0.6 (4) | C482—C481—C486—C485 | 0.0 (4) |
N28—C281—C286—C285 | −177.8 (2) | N48—C481—C486—C485 | 179.5 (2) |
C284—C285—C286—C281 | 0.0 (4) | C484—C485—C486—C481 | −0.4 (4) |
C27A—N28—N29—C210 | 0.9 (3) | C47A—N48—N49—C410 | 1.8 (3) |
C281—N28—N29—C210 | 177.4 (2) | C481—N48—N49—C410 | −176.2 (2) |
N28—N29—C210—C21A | −0.5 (3) | N48—N49—C410—C41A | −0.4 (3) |
N28—N29—C210—C211 | 179.4 (2) | N48—N49—C410—C411 | 179.1 (2) |
N27—C27A—C21A—C220 | −0.2 (4) | N47—C47A—C41A—C420 | 2.9 (4) |
N28—C27A—C21A—C220 | 176.7 (2) | N48—C47A—C41A—C420 | 179.4 (2) |
N27—C27A—C21A—C210 | −176.4 (2) | N47—C47A—C41A—C410 | −174.3 (2) |
N28—C27A—C21A—C210 | 0.5 (3) | N48—C47A—C41A—C410 | 2.2 (3) |
N29—C210—C21A—C27A | 0.0 (3) | N49—C410—C41A—C47A | −1.1 (3) |
C211—C210—C21A—C27A | −179.9 (3) | C411—C410—C41A—C47A | 179.4 (3) |
N29—C210—C21A—C220 | −175.0 (3) | N49—C410—C41A—C420 | −177.5 (3) |
C211—C210—C21A—C220 | 5.1 (5) | C411—C410—C41A—C420 | 3.0 (5) |
C27A—C21A—C220—C22A | 2.4 (3) | C47A—C41A—C420—C42A | −1.4 (3) |
C210—C21A—C220—C22A | 176.9 (3) | C410—C41A—C420—C42A | 174.7 (3) |
C27A—C21A—C220—C221 | −176.1 (2) | C47A—C41A—C420—C421 | 177.2 (2) |
C210—C21A—C220—C221 | −1.5 (4) | C410—C41A—C420—C421 | −6.7 (4) |
C22A—C220—C221—C226 | 118.8 (3) | C42A—C420—C421—C422 | −70.2 (3) |
C21A—C220—C221—C226 | −62.8 (3) | C41A—C420—C421—C422 | 111.4 (3) |
C22A—C220—C221—C222 | −60.5 (3) | C42A—C420—C421—C426 | 111.5 (3) |
C21A—C220—C221—C222 | 117.8 (3) | C41A—C420—C421—C426 | −67.0 (3) |
C226—C221—C222—C223 | −0.3 (4) | C426—C421—C422—C423 | 0.9 (4) |
C220—C221—C222—C223 | 179.0 (2) | C420—C421—C422—C423 | −177.5 (2) |
C221—C222—C223—C224 | 0.2 (4) | C421—C422—C423—C424 | −0.5 (4) |
C222—C223—C224—O224 | −179.4 (2) | C422—C423—C424—O424 | 180.0 (2) |
C222—C223—C224—C225 | 0.3 (4) | C422—C423—C424—C425 | −0.6 (4) |
C223—C224—O224—C227 | 6.0 (4) | C425—C424—O424—C427 | 178.4 (2) |
C225—C224—O224—C227 | −173.7 (2) | C423—C424—O424—C427 | −2.2 (4) |
O224—C224—C225—C226 | 178.9 (2) | O424—C424—C425—C426 | −179.3 (2) |
C223—C224—C225—C226 | −0.8 (4) | C423—C424—C425—C426 | 1.2 (4) |
C224—C225—C226—C221 | 0.7 (4) | C424—C425—C426—C421 | −0.8 (4) |
C222—C221—C226—C225 | −0.1 (4) | C422—C421—C426—C425 | −0.2 (4) |
C220—C221—C226—C225 | −179.5 (2) | C420—C421—C426—C425 | 178.2 (2) |
C21A—C220—C22A—C26A | −3.0 (3) | C41A—C420—C42A—C46A | −1.7 (3) |
C221—C220—C22A—C26A | 175.4 (2) | C421—C420—C42A—C46A | 179.9 (2) |
C21A—C220—C22A—C22B | 177.0 (2) | C41A—C420—C42A—C42B | 178.8 (2) |
C221—C220—C22A—C22B | −4.6 (4) | C421—C420—C42A—C42B | 0.3 (4) |
N27—C26A—C22A—C220 | 1.6 (4) | N47—C46A—C42A—C420 | 3.9 (4) |
C26—C26A—C22A—C220 | −176.5 (2) | C46—C46A—C42A—C420 | −175.1 (2) |
N27—C26A—C22A—C22B | −178.4 (2) | N47—C46A—C42A—C42B | −176.5 (2) |
C26—C26A—C22A—C22B | 3.4 (3) | C46—C46A—C42A—C42B | 4.5 (3) |
C22—C21—C22B—C24A | −2.1 (4) | C42—C41—C42B—C44A | −2.2 (4) |
C22—C21—C22B—C22A | −180.0 (2) | C42—C41—C42B—C42A | 179.2 (2) |
C24—C24A—C22B—C21 | 2.3 (3) | C44—C44A—C42B—C41 | 1.7 (4) |
C25—C24A—C22B—C21 | −174.9 (2) | C45—C44A—C42B—C41 | −177.1 (2) |
C24—C24A—C22B—C22A | −179.7 (2) | C44—C44A—C42B—C42A | −179.7 (2) |
C25—C24A—C22B—C22A | 3.1 (3) | C45—C44A—C42B—C42A | 1.5 (3) |
C220—C22A—C22B—C21 | −28.1 (4) | C420—C42A—C42B—C41 | −27.4 (4) |
C26A—C22A—C22B—C21 | 151.9 (2) | C46A—C42A—C42B—C41 | 153.1 (2) |
C220—C22A—C22B—C24A | 153.9 (2) | C420—C42A—C42B—C44A | 154.1 (2) |
C26A—C22A—C22B—C24A | −26.0 (3) | C46A—C42A—C42B—C44A | −25.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···N39 | 0.95 | 2.60 | 3.504 (3) | 159 |
C326—H326···N47 | 0.95 | 2.59 | 3.526 (3) | 168 |
C122—H122···Cg11 | 0.95 | 2.77 | 3.542 (3) | 139 |
C222—H222···Cg12i | 0.95 | 2.77 | 3.568 (3) | 142 |
C225—H225···Cg8ii | 0.95 | 2.76 | 3.628 (3) | 152 |
C322—H322···Cg7iii | 0.95 | 2.77 | 3.483 (3) | 132 |
C422—H422···Cg9 | 0.95 | 2.83 | 3.693 (3) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
C30H27N3O3 | F(000) = 1008 |
Mr = 477.55 | Dx = 1.309 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 5103 reflections |
a = 10.4716 (9) Å | θ = 2.0–27.5° |
b = 20.0027 (18) Å | µ = 0.09 mm−1 |
c = 12.1529 (9) Å | T = 120 K |
β = 107.818 (4)° | Plate, colourless |
V = 2423.4 (4) Å3 | 0.60 × 0.30 × 0.02 mm |
Z = 4 |
Bruker-Nonius KappaCCD diffractometer | 2720 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1499 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.199 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.0° |
ϕ & ω scans | h = −13→13 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −25→25 |
Tmin = 0.963, Tmax = 0.998 | l = −13→15 |
20344 measured reflections |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2720 reflections | Δρmax = 0.45 e Å−3 |
329 parameters | Δρmin = −0.55 e Å−3 |
2 restraints | Absolute structure: Friedel pairs merged |
Primary atom site location: structure-invariant direct methods |
C30H27N3O3 | V = 2423.4 (4) Å3 |
Mr = 477.55 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.4716 (9) Å | µ = 0.09 mm−1 |
b = 20.0027 (18) Å | T = 120 K |
c = 12.1529 (9) Å | 0.60 × 0.30 × 0.02 mm |
β = 107.818 (4)° |
Bruker-Nonius KappaCCD diffractometer | 2720 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1499 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.998 | Rint = 0.199 |
20344 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 2 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.45 e Å−3 |
2720 reflections | Δρmin = −0.55 e Å−3 |
329 parameters | Absolute structure: Friedel pairs merged |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3263 (5) | 0.4933 (3) | 0.5653 (5) | 0.0304 (14) | |
C2 | 0.2303 (6) | 0.4752 (3) | 0.6162 (5) | 0.0350 (14) | |
C3 | 0.1556 (6) | 0.4177 (3) | 0.5833 (5) | 0.0378 (15) | |
C4 | 0.1805 (6) | 0.3765 (3) | 0.5016 (5) | 0.0359 (15) | |
C4A | 0.2751 (6) | 0.3935 (3) | 0.4474 (5) | 0.0301 (13) | |
C5 | 0.3078 (6) | 0.3481 (3) | 0.3605 (5) | 0.0342 (14) | |
C6 | 0.4592 (6) | 0.3486 (3) | 0.3795 (6) | 0.0333 (14) | |
C6A | 0.5020 (5) | 0.4194 (3) | 0.3676 (5) | 0.0259 (13) | |
N7 | 0.5952 (4) | 0.4266 (2) | 0.3142 (4) | 0.0262 (10) | |
C7A | 0.6217 (5) | 0.4911 (3) | 0.2956 (5) | 0.0254 (12) | |
N8 | 0.7079 (5) | 0.5120 (2) | 0.2383 (4) | 0.0281 (11) | |
C81 | 0.7957 (5) | 0.4746 (3) | 0.1944 (5) | 0.0270 (13) | |
C82 | 0.8051 (6) | 0.4881 (3) | 0.0857 (5) | 0.0328 (14) | |
C83 | 0.8892 (6) | 0.4505 (3) | 0.0423 (6) | 0.0363 (15) | |
C84 | 0.9624 (6) | 0.3979 (3) | 0.1052 (6) | 0.0388 (16) | |
C85 | 0.9541 (6) | 0.3852 (3) | 0.2137 (5) | 0.0354 (14) | |
C86 | 0.8713 (5) | 0.4233 (3) | 0.2602 (5) | 0.0294 (13) | |
N9 | 0.6988 (5) | 0.5813 (2) | 0.2232 (4) | 0.0307 (12) | |
C10 | 0.6125 (6) | 0.6029 (3) | 0.2741 (5) | 0.0276 (13) | |
C101 | 0.5771 (7) | 0.6761 (3) | 0.2662 (6) | 0.0420 (16) | |
C10A | 0.5613 (5) | 0.5479 (3) | 0.3251 (5) | 0.0237 (12) | |
C11 | 0.4722 (5) | 0.5394 (3) | 0.3887 (5) | 0.0262 (13) | |
C111 | 0.4177 (5) | 0.5994 (3) | 0.4335 (5) | 0.0258 (12) | |
C112 | 0.2810 (5) | 0.6152 (3) | 0.3975 (5) | 0.0256 (13) | |
C113 | 0.2364 (5) | 0.6698 (3) | 0.4464 (5) | 0.0264 (13) | |
O13 | 0.1052 (3) | 0.68897 (19) | 0.4203 (3) | 0.0302 (9) | |
C13 | 0.0082 (6) | 0.6530 (3) | 0.3327 (5) | 0.0338 (14) | |
C114 | 0.3277 (5) | 0.7093 (3) | 0.5287 (5) | 0.0234 (12) | |
O14 | 0.2818 (4) | 0.76181 (18) | 0.5785 (3) | 0.0303 (9) | |
C14 | 0.2968 (6) | 0.8242 (3) | 0.5245 (5) | 0.0317 (14) | |
C115 | 0.4630 (5) | 0.6951 (3) | 0.5602 (5) | 0.0272 (13) | |
O15 | 0.5445 (4) | 0.73834 (18) | 0.6382 (3) | 0.0321 (9) | |
C15 | 0.6852 (5) | 0.7236 (3) | 0.6786 (5) | 0.0325 (14) | |
C116 | 0.5102 (5) | 0.6400 (3) | 0.5138 (5) | 0.0260 (12) | |
C12A | 0.4414 (5) | 0.4727 (3) | 0.4124 (5) | 0.0267 (13) | |
C12B | 0.3464 (5) | 0.4536 (3) | 0.4757 (5) | 0.0269 (13) | |
H1 | 0.3788 | 0.5324 | 0.5904 | 0.036* | |
H2 | 0.2154 | 0.5027 | 0.6748 | 0.042* | |
H3 | 0.0875 | 0.4066 | 0.6169 | 0.045* | |
H4 | 0.1322 | 0.3358 | 0.4819 | 0.043* | |
H5A | 0.2599 | 0.3635 | 0.2811 | 0.041* | |
H5B | 0.2779 | 0.3020 | 0.3693 | 0.041* | |
H6A | 0.5072 | 0.3313 | 0.4575 | 0.040* | |
H6B | 0.4809 | 0.3196 | 0.3217 | 0.040* | |
H82 | 0.7537 | 0.5233 | 0.0409 | 0.039* | |
H83 | 0.8970 | 0.4608 | −0.0317 | 0.044* | |
H84 | 1.0175 | 0.3711 | 0.0736 | 0.047* | |
H85 | 1.0056 | 0.3499 | 0.2580 | 0.042* | |
H86 | 0.8667 | 0.4143 | 0.3357 | 0.035* | |
H10A | 0.6100 | 0.6963 | 0.3432 | 0.050* | |
H10B | 0.4795 | 0.6812 | 0.2362 | 0.050* | |
H10C | 0.6189 | 0.6983 | 0.2141 | 0.050* | |
H112 | 0.2193 | 0.5889 | 0.3403 | 0.031* | |
H13A | 0.0273 | 0.6579 | 0.2591 | 0.041* | |
H13B | −0.0815 | 0.6706 | 0.3249 | 0.041* | |
H13C | 0.0118 | 0.6055 | 0.3537 | 0.041* | |
H14A | 0.3912 | 0.8306 | 0.5294 | 0.038* | |
H14B | 0.2676 | 0.8611 | 0.5642 | 0.038* | |
H14C | 0.2419 | 0.8234 | 0.4432 | 0.038* | |
H15A | 0.6991 | 0.6802 | 0.7180 | 0.039* | |
H15B | 0.7320 | 0.7585 | 0.7325 | 0.039* | |
H15C | 0.7206 | 0.7220 | 0.6127 | 0.039* | |
H116 | 0.6033 | 0.6301 | 0.5363 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.021 (3) | 0.037 (3) | 0.027 (3) | 0.002 (3) | −0.003 (3) | 0.003 (3) |
C2 | 0.027 (3) | 0.047 (4) | 0.030 (3) | 0.003 (3) | 0.007 (3) | 0.002 (3) |
C3 | 0.029 (3) | 0.048 (4) | 0.037 (4) | −0.003 (3) | 0.010 (3) | 0.007 (3) |
C4 | 0.026 (3) | 0.037 (3) | 0.041 (4) | −0.007 (3) | 0.004 (3) | 0.007 (3) |
C4A | 0.027 (3) | 0.032 (3) | 0.030 (3) | −0.003 (3) | 0.006 (3) | 0.002 (3) |
C5 | 0.029 (3) | 0.031 (3) | 0.043 (4) | −0.005 (3) | 0.012 (3) | 0.000 (3) |
C6 | 0.029 (3) | 0.024 (3) | 0.049 (4) | −0.003 (2) | 0.015 (3) | −0.001 (3) |
C6A | 0.022 (3) | 0.023 (3) | 0.029 (3) | 0.003 (2) | 0.003 (3) | 0.002 (2) |
N7 | 0.022 (2) | 0.021 (2) | 0.034 (3) | −0.0006 (19) | 0.007 (2) | −0.003 (2) |
C7A | 0.020 (3) | 0.030 (3) | 0.025 (3) | 0.000 (3) | 0.006 (2) | −0.001 (3) |
N8 | 0.033 (3) | 0.018 (2) | 0.035 (3) | 0.001 (2) | 0.014 (2) | −0.001 (2) |
C81 | 0.020 (3) | 0.027 (3) | 0.032 (4) | −0.005 (2) | 0.004 (3) | −0.001 (3) |
C82 | 0.030 (3) | 0.032 (3) | 0.035 (4) | 0.002 (3) | 0.007 (3) | 0.004 (3) |
C83 | 0.031 (3) | 0.047 (4) | 0.035 (3) | −0.003 (3) | 0.014 (3) | −0.001 (3) |
C84 | 0.030 (3) | 0.046 (4) | 0.042 (4) | 0.010 (3) | 0.015 (3) | −0.008 (3) |
C85 | 0.027 (3) | 0.042 (4) | 0.035 (4) | 0.004 (3) | 0.006 (3) | 0.006 (3) |
C86 | 0.026 (3) | 0.035 (3) | 0.029 (3) | 0.002 (3) | 0.009 (3) | 0.003 (3) |
N9 | 0.030 (3) | 0.031 (3) | 0.031 (3) | −0.001 (2) | 0.009 (2) | 0.002 (2) |
C10 | 0.030 (3) | 0.027 (3) | 0.027 (3) | 0.002 (3) | 0.010 (3) | 0.001 (3) |
C101 | 0.051 (4) | 0.032 (4) | 0.050 (4) | 0.000 (3) | 0.026 (3) | 0.001 (3) |
C10A | 0.024 (3) | 0.023 (3) | 0.022 (3) | 0.000 (2) | 0.005 (2) | −0.003 (2) |
C11 | 0.022 (3) | 0.028 (3) | 0.026 (3) | −0.004 (2) | 0.003 (2) | −0.005 (3) |
C111 | 0.027 (3) | 0.022 (3) | 0.029 (3) | 0.002 (2) | 0.009 (3) | 0.004 (2) |
C112 | 0.023 (3) | 0.023 (3) | 0.027 (3) | −0.004 (2) | 0.002 (3) | 0.001 (2) |
C113 | 0.027 (3) | 0.026 (3) | 0.028 (3) | 0.004 (2) | 0.011 (3) | 0.006 (3) |
O13 | 0.022 (2) | 0.031 (2) | 0.035 (2) | 0.0009 (17) | 0.0045 (17) | −0.0029 (18) |
C13 | 0.022 (3) | 0.041 (4) | 0.037 (3) | −0.004 (3) | 0.007 (3) | −0.005 (3) |
C114 | 0.028 (3) | 0.023 (3) | 0.020 (3) | 0.002 (2) | 0.008 (2) | 0.000 (2) |
O14 | 0.036 (2) | 0.028 (2) | 0.032 (2) | 0.0027 (18) | 0.0170 (18) | −0.0018 (18) |
C14 | 0.032 (3) | 0.024 (3) | 0.040 (4) | 0.003 (3) | 0.012 (3) | −0.004 (3) |
C115 | 0.025 (3) | 0.025 (3) | 0.030 (3) | 0.003 (2) | 0.007 (3) | 0.000 (2) |
O15 | 0.028 (2) | 0.029 (2) | 0.034 (2) | 0.0010 (18) | 0.0006 (18) | −0.0062 (19) |
C15 | 0.026 (3) | 0.036 (3) | 0.032 (3) | 0.002 (3) | 0.003 (3) | −0.007 (3) |
C116 | 0.021 (3) | 0.026 (3) | 0.032 (3) | 0.002 (2) | 0.010 (2) | 0.003 (2) |
C12A | 0.017 (3) | 0.030 (3) | 0.030 (3) | −0.001 (2) | 0.003 (2) | 0.000 (3) |
C12B | 0.020 (3) | 0.027 (3) | 0.032 (3) | 0.002 (2) | 0.005 (2) | 0.005 (3) |
C1—C2 | 1.380 (8) | C86—H86 | 0.95 |
C1—C12B | 1.415 (8) | N9—C10 | 1.313 (7) |
C1—H1 | 0.95 | C10—C10A | 1.444 (8) |
C2—C3 | 1.380 (9) | C10—C101 | 1.506 (8) |
C2—H2 | 0.95 | C101—H10A | 0.98 |
C3—C4 | 1.375 (9) | C101—H10B | 0.98 |
C3—H3 | 0.95 | C101—H10C | 0.98 |
C4—C4A | 1.390 (8) | C10A—C11 | 1.392 (8) |
C4—H4 | 0.95 | C11—C12A | 1.423 (7) |
C4A—C12B | 1.401 (8) | C11—C111 | 1.502 (8) |
C4A—C5 | 1.510 (8) | C111—C112 | 1.399 (7) |
C5—C6 | 1.530 (8) | C111—C116 | 1.404 (8) |
C5—H5A | 0.99 | C112—C113 | 1.390 (7) |
C5—H5B | 0.99 | C112—H112 | 0.95 |
C6—C6A | 1.506 (8) | C113—O13 | 1.367 (6) |
C6—H6A | 0.99 | C113—C114 | 1.397 (7) |
C6—H6B | 0.99 | O13—C13 | 1.422 (7) |
C6A—N7 | 1.334 (7) | C13—H13A | 0.98 |
C6A—C12A | 1.430 (7) | C13—H13B | 0.98 |
N7—C7A | 1.352 (7) | C13—H13C | 0.98 |
C7A—N8 | 1.363 (7) | C114—O14 | 1.371 (6) |
C7A—C10A | 1.400 (8) | C114—C115 | 1.380 (7) |
N8—N9 | 1.398 (6) | O14—C14 | 1.441 (7) |
N8—C81 | 1.411 (7) | C14—H14A | 0.98 |
C81—C82 | 1.381 (8) | C14—H14B | 0.98 |
C81—C86 | 1.389 (8) | C14—H14C | 0.98 |
C82—C83 | 1.380 (9) | C115—O15 | 1.371 (6) |
C82—H82 | 0.95 | C115—C116 | 1.395 (8) |
C83—C84 | 1.386 (9) | O15—C15 | 1.434 (7) |
C83—H83 | 0.95 | C15—H15A | 0.98 |
C84—C85 | 1.372 (9) | C15—H15B | 0.98 |
C84—H84 | 0.95 | C15—H15C | 0.98 |
C85—C86 | 1.398 (8) | C116—H116 | 0.95 |
C85—H85 | 0.95 | C12A—C12B | 1.481 (8) |
C2—C1—C12B | 119.8 (5) | C10A—C10—C101 | 130.6 (5) |
C2—C1—H1 | 120.1 | C10—C101—H10A | 109.5 |
C12B—C1—H1 | 120.1 | C10—C101—H10B | 109.5 |
C1—C2—C3 | 121.1 (6) | H10A—C101—H10B | 109.5 |
C1—C2—H2 | 119.5 | C10—C101—H10C | 109.5 |
C3—C2—H2 | 119.5 | H10A—C101—H10C | 109.5 |
C4—C3—C2 | 119.5 (6) | H10B—C101—H10C | 109.5 |
C4—C3—H3 | 120.3 | C11—C10A—C7A | 118.3 (5) |
C2—C3—H3 | 120.3 | C11—C10A—C10 | 137.1 (5) |
C3—C4—C4A | 121.1 (6) | C7A—C10A—C10 | 104.6 (5) |
C3—C4—H4 | 119.5 | C10A—C11—C12A | 117.4 (5) |
C4A—C4—H4 | 119.5 | C10A—C11—C111 | 119.8 (5) |
C4—C4A—C12B | 119.8 (5) | C12A—C11—C111 | 122.7 (5) |
C4—C4A—C5 | 122.1 (5) | C112—C111—C116 | 120.6 (5) |
C12B—C4A—C5 | 118.1 (5) | C112—C111—C11 | 122.3 (5) |
C4A—C5—C6 | 109.7 (5) | C116—C111—C11 | 117.2 (5) |
C4A—C5—H5A | 109.7 | C113—C112—C111 | 119.3 (5) |
C6—C5—H5A | 109.7 | C113—C112—H112 | 120.4 |
C4A—C5—H5B | 109.7 | C111—C112—H112 | 120.4 |
C6—C5—H5B | 109.7 | O13—C113—C112 | 124.5 (5) |
H5A—C5—H5B | 108.2 | O13—C113—C114 | 115.2 (4) |
C6A—C6—C5 | 108.5 (5) | C112—C113—C114 | 120.3 (5) |
C6A—C6—H6A | 110.0 | C113—O13—C13 | 118.0 (4) |
C5—C6—H6A | 110.0 | O13—C13—H13A | 109.5 |
C6A—C6—H6B | 110.0 | O13—C13—H13B | 109.5 |
C5—C6—H6B | 110.0 | H13A—C13—H13B | 109.5 |
H6A—C6—H6B | 108.4 | O13—C13—H13C | 109.5 |
N7—C6A—C12A | 125.5 (5) | H13A—C13—H13C | 109.5 |
N7—C6A—C6 | 115.6 (5) | H13B—C13—H13C | 109.5 |
C12A—C6A—C6 | 118.9 (5) | O14—C114—C115 | 120.3 (5) |
C6A—N7—C7A | 113.8 (5) | O14—C114—C113 | 119.6 (5) |
N7—C7A—N8 | 125.5 (5) | C115—C114—C113 | 120.1 (5) |
N7—C7A—C10A | 126.8 (5) | C114—O14—C14 | 111.1 (4) |
N8—C7A—C10A | 107.6 (5) | O14—C14—H14A | 109.5 |
C7A—N8—N9 | 110.0 (4) | O14—C14—H14B | 109.5 |
C7A—N8—C81 | 129.8 (4) | H14A—C14—H14B | 109.5 |
N9—N8—C81 | 120.1 (4) | O14—C14—H14C | 109.5 |
C82—C81—C86 | 120.0 (5) | H14A—C14—H14C | 109.5 |
C82—C81—N8 | 120.2 (5) | H14B—C14—H14C | 109.5 |
C86—C81—N8 | 119.8 (5) | O15—C115—C114 | 115.5 (5) |
C83—C82—C81 | 120.0 (6) | O15—C115—C116 | 123.8 (5) |
C83—C82—H82 | 120.0 | C114—C115—C116 | 120.7 (5) |
C81—C82—H82 | 120.0 | C115—O15—C15 | 117.6 (4) |
C82—C83—C84 | 120.9 (6) | O15—C15—H15A | 109.5 |
C82—C83—H83 | 119.6 | O15—C15—H15B | 109.5 |
C84—C83—H83 | 119.6 | H15A—C15—H15B | 109.5 |
C85—C84—C83 | 118.9 (6) | O15—C15—H15C | 109.5 |
C85—C84—H84 | 120.5 | H15A—C15—H15C | 109.5 |
C83—C84—H84 | 120.5 | H15B—C15—H15C | 109.5 |
C84—C85—C86 | 121.2 (6) | C115—C116—C111 | 118.9 (5) |
C84—C85—H85 | 119.4 | C115—C116—H116 | 120.5 |
C86—C85—H85 | 119.4 | C111—C116—H116 | 120.5 |
C81—C86—C85 | 119.0 (5) | C11—C12A—C6A | 117.8 (5) |
C81—C86—H86 | 120.5 | C11—C12A—C12B | 125.2 (5) |
C85—C86—H86 | 120.5 | C6A—C12A—C12B | 117.0 (5) |
C10—N9—N8 | 107.0 (4) | C4A—C12B—C1 | 118.5 (5) |
N9—C10—C10A | 110.6 (5) | C4A—C12B—C12A | 119.0 (5) |
N9—C10—C101 | 118.7 (5) | C1—C12B—C12A | 122.5 (5) |
C12B—C1—C2—C3 | 1.8 (9) | C10—C10A—C11—C111 | −8.6 (10) |
C1—C2—C3—C4 | 2.4 (9) | C10A—C11—C111—C112 | 116.6 (6) |
C2—C3—C4—C4A | −3.2 (9) | C12A—C11—C111—C112 | −66.2 (7) |
C3—C4—C4A—C12B | −0.2 (9) | C10A—C11—C111—C116 | −63.1 (7) |
C3—C4—C4A—C5 | 177.8 (6) | C12A—C11—C111—C116 | 114.1 (6) |
C4—C4A—C5—C6 | −139.5 (6) | C116—C111—C112—C113 | −3.2 (8) |
C12B—C4A—C5—C6 | 38.5 (7) | C11—C111—C112—C113 | 177.1 (5) |
C4A—C5—C6—C6A | −58.4 (6) | C111—C112—C113—O13 | −178.3 (5) |
C5—C6—C6A—N7 | −141.3 (5) | C111—C112—C113—C114 | 1.5 (7) |
C5—C6—C6A—C12A | 38.4 (7) | C112—C113—O13—C13 | −3.5 (7) |
C12A—C6A—N7—C7A | −5.6 (7) | C114—C113—O13—C13 | 176.7 (5) |
C6—C6A—N7—C7A | 174.1 (5) | O13—C113—C114—O14 | 1.7 (7) |
C6A—N7—C7A—N8 | −176.8 (5) | C112—C113—C114—O14 | −178.2 (5) |
C6A—N7—C7A—C10A | −0.8 (8) | O13—C113—C114—C115 | −178.9 (5) |
N7—C7A—N8—N9 | 172.9 (5) | C112—C113—C114—C115 | 1.2 (7) |
C10A—C7A—N8—N9 | −3.8 (6) | C115—C114—O14—C14 | 81.2 (6) |
N7—C7A—N8—C81 | −5.8 (9) | C113—C114—O14—C14 | −99.4 (5) |
C10A—C7A—N8—C81 | 177.5 (5) | O14—C114—C115—O15 | −2.9 (7) |
C7A—N8—C81—C82 | 136.1 (6) | C113—C114—C115—O15 | 177.7 (5) |
N9—N8—C81—C82 | −42.5 (7) | O14—C114—C115—C116 | 177.1 (5) |
C7A—N8—C81—C86 | −42.9 (8) | C113—C114—C115—C116 | −2.3 (8) |
N9—N8—C81—C86 | 138.6 (5) | C114—C115—O15—C15 | 176.6 (5) |
C86—C81—C82—C83 | 0.3 (8) | C116—C115—O15—C15 | −3.5 (7) |
N8—C81—C82—C83 | −178.7 (5) | O15—C115—C116—C111 | −179.3 (5) |
C81—C82—C83—C84 | 1.6 (9) | C114—C115—C116—C111 | 0.6 (8) |
C82—C83—C84—C85 | −2.4 (10) | C112—C111—C116—C115 | 2.1 (8) |
C83—C84—C85—C86 | 1.4 (9) | C11—C111—C116—C115 | −178.1 (5) |
C82—C81—C86—C85 | −1.3 (8) | C10A—C11—C12A—C6A | −1.1 (7) |
N8—C81—C86—C85 | 177.7 (5) | C111—C11—C12A—C6A | −178.4 (5) |
C84—C85—C86—C81 | 0.4 (9) | C10A—C11—C12A—C12B | −178.2 (5) |
C7A—N8—N9—C10 | 2.3 (6) | C111—C11—C12A—C12B | 4.5 (8) |
C81—N8—N9—C10 | −178.8 (5) | N7—C6A—C12A—C11 | 6.7 (8) |
N8—N9—C10—C10A | 0.0 (6) | C6—C6A—C12A—C11 | −173.0 (5) |
N8—N9—C10—C101 | −176.9 (5) | N7—C6A—C12A—C12B | −176.0 (5) |
N7—C7A—C10A—C11 | 5.8 (8) | C6—C6A—C12A—C12B | 4.3 (7) |
N8—C7A—C10A—C11 | −177.6 (5) | C4—C4A—C12B—C1 | 4.4 (8) |
N7—C7A—C10A—C10 | −173.1 (6) | C5—C4A—C12B—C1 | −173.7 (5) |
N8—C7A—C10A—C10 | 3.6 (6) | C4—C4A—C12B—C12A | −176.7 (5) |
N9—C10—C10A—C11 | 179.2 (6) | C5—C4A—C12B—C12A | 5.2 (8) |
C101—C10—C10A—C11 | −4.4 (11) | C2—C1—C12B—C4A | −5.2 (8) |
N9—C10—C10A—C7A | −2.2 (6) | C2—C1—C12B—C12A | 175.9 (5) |
C101—C10—C10A—C7A | 174.2 (6) | C11—C12A—C12B—C4A | 148.9 (5) |
C7A—C10A—C11—C12A | −4.4 (7) | C6A—C12A—C12B—C4A | −28.2 (7) |
C10—C10A—C11—C12A | 174.0 (6) | C11—C12A—C12B—C1 | −32.2 (8) |
C7A—C10A—C11—C111 | 173.0 (5) | C6A—C12A—C12B—C1 | 150.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C82—H82···Cg13i | 0.95 | 2.73 | 3.472 (6) | 130 |
Symmetry code: (i) x+1, −y, z−1/2. |
C26H18N4 | F(000) = 808 |
Mr = 386.44 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4372 reflections |
a = 11.3560 (3) Å | θ = 2.9–27.5° |
b = 17.3507 (5) Å | µ = 0.08 mm−1 |
c = 9.7577 (2) Å | T = 120 K |
β = 97.262 (2)° | Lath, colourless |
V = 1907.18 (8) Å3 | 0.50 × 0.24 × 0.10 mm |
Z = 4 |
Bruker-Nonius KappaCCD diffractometer | 4372 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2818 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ϕ & ω scans | h = −14→14 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −22→21 |
Tmin = 0.971, Tmax = 0.992 | l = −12→12 |
26391 measured reflections |
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) = 0.142 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0831P)2] where P = (Fo2 + 2Fc2)/3 |
4372 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C26H18N4 | V = 1907.18 (8) Å3 |
Mr = 386.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.3560 (3) Å | µ = 0.08 mm−1 |
b = 17.3507 (5) Å | T = 120 K |
c = 9.7577 (2) Å | 0.50 × 0.24 × 0.10 mm |
β = 97.262 (2)° |
Bruker-Nonius KappaCCD diffractometer | 4372 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2818 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.992 | Rint = 0.064 |
26391 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.33 e Å−3 |
4372 reflections | Δρmin = −0.34 e Å−3 |
272 parameters |
Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.21448 (15) | 0.35074 (10) | 0.50320 (16) | 0.0270 (4) | |
C2 | 0.15537 (16) | 0.29981 (10) | 0.57854 (17) | 0.0300 (4) | |
C3 | 0.21775 (16) | 0.24243 (10) | 0.65708 (17) | 0.0319 (4) | |
C4 | 0.33858 (16) | 0.23696 (11) | 0.65857 (18) | 0.0364 (5) | |
C4A | 0.40076 (15) | 0.28765 (10) | 0.58222 (16) | 0.0284 (4) | |
C5 | 0.52758 (16) | 0.28100 (11) | 0.5806 (2) | 0.0398 (5) | |
C6 | 0.58638 (16) | 0.32743 (11) | 0.50234 (19) | 0.0373 (5) | |
C6A | 0.52606 (14) | 0.38826 (9) | 0.41853 (15) | 0.0238 (4) | |
C7 | 0.58593 (14) | 0.43595 (9) | 0.33297 (15) | 0.0230 (4) | |
C71 | 0.71477 (14) | 0.42529 (9) | 0.32303 (16) | 0.0235 (4) | |
C72 | 0.80096 (15) | 0.43672 (10) | 0.43597 (17) | 0.0280 (4) | |
C73 | 0.91823 (15) | 0.42338 (10) | 0.42185 (17) | 0.0284 (4) | |
N74 | 0.95701 (12) | 0.40019 (8) | 0.30454 (14) | 0.0305 (4) | |
C75 | 0.87328 (15) | 0.38993 (10) | 0.19608 (17) | 0.0306 (4) | |
C76 | 0.75347 (15) | 0.40106 (10) | 0.20057 (16) | 0.0268 (4) | |
C7A | 0.51852 (14) | 0.49169 (9) | 0.25525 (15) | 0.0224 (4) | |
C8 | 0.53921 (15) | 0.55383 (9) | 0.16384 (16) | 0.0260 (4) | |
C81 | 0.65178 (15) | 0.58037 (11) | 0.11540 (18) | 0.0323 (4) | |
N9 | 0.43940 (12) | 0.59074 (8) | 0.12348 (13) | 0.0278 (4) | |
N10 | 0.35014 (12) | 0.55494 (8) | 0.18465 (13) | 0.0250 (3) | |
C101 | 0.23473 (15) | 0.58816 (10) | 0.17145 (16) | 0.0252 (4) | |
C102 | 0.22343 (16) | 0.66740 (10) | 0.15336 (17) | 0.0337 (4) | |
C103 | 0.11157 (18) | 0.70048 (11) | 0.13938 (18) | 0.0404 (5) | |
C104 | 0.01195 (18) | 0.65562 (12) | 0.14412 (17) | 0.0393 (5) | |
C105 | 0.02419 (16) | 0.57690 (12) | 0.16256 (18) | 0.0374 (5) | |
C106 | 0.13528 (15) | 0.54244 (10) | 0.17547 (17) | 0.0297 (4) | |
C10A | 0.39630 (14) | 0.49528 (9) | 0.26704 (15) | 0.0223 (4) | |
N11 | 0.33552 (12) | 0.45111 (7) | 0.34522 (13) | 0.0223 (3) | |
C11A | 0.40127 (14) | 0.39777 (9) | 0.42079 (15) | 0.0211 (4) | |
C11B | 0.33774 (14) | 0.34580 (9) | 0.50358 (15) | 0.0223 (4) | |
H1 | 0.1711 | 0.3897 | 0.4503 | 0.032* | |
H2 | 0.0718 | 0.3038 | 0.5770 | 0.036* | |
H3 | 0.1770 | 0.2074 | 0.7092 | 0.038* | |
H4 | 0.3809 | 0.1979 | 0.7126 | 0.044* | |
H5 | 0.5704 | 0.2429 | 0.6363 | 0.048* | |
H6 | 0.6693 | 0.3203 | 0.5018 | 0.045* | |
H72 | 0.7790 | 0.4536 | 0.5218 | 0.034* | |
H73 | 0.9754 | 0.4311 | 0.5005 | 0.034* | |
H75 | 0.8980 | 0.3740 | 0.1110 | 0.037* | |
H76 | 0.6980 | 0.3922 | 0.1207 | 0.032* | |
H81A | 0.6802 | 0.5410 | 0.0555 | 0.048* | |
H81B | 0.7118 | 0.5890 | 0.1953 | 0.048* | |
H81C | 0.6374 | 0.6286 | 0.0636 | 0.048* | |
H102 | 0.2918 | 0.6986 | 0.1506 | 0.040* | |
H103 | 0.1034 | 0.7546 | 0.1264 | 0.049* | |
H104 | −0.0645 | 0.6786 | 0.1348 | 0.047* | |
H105 | −0.0444 | 0.5460 | 0.1664 | 0.045* | |
H106 | 0.1430 | 0.4882 | 0.1869 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0276 (10) | 0.0283 (9) | 0.0246 (8) | 0.0035 (7) | 0.0020 (7) | 0.0017 (7) |
C2 | 0.0284 (10) | 0.0343 (10) | 0.0278 (9) | −0.0006 (8) | 0.0051 (7) | 0.0001 (8) |
C3 | 0.0369 (11) | 0.0327 (10) | 0.0270 (9) | −0.0021 (8) | 0.0073 (8) | 0.0048 (8) |
C4 | 0.0393 (12) | 0.0350 (11) | 0.0349 (10) | 0.0065 (9) | 0.0047 (8) | 0.0132 (8) |
C4A | 0.0322 (10) | 0.0270 (9) | 0.0260 (9) | 0.0035 (8) | 0.0032 (7) | 0.0017 (7) |
C5 | 0.0306 (11) | 0.0411 (11) | 0.0475 (11) | 0.0114 (9) | 0.0032 (9) | 0.0193 (9) |
C6 | 0.0255 (10) | 0.0453 (12) | 0.0416 (10) | 0.0114 (9) | 0.0057 (8) | 0.0142 (9) |
C6A | 0.0233 (9) | 0.0251 (9) | 0.0229 (8) | 0.0047 (7) | 0.0024 (7) | −0.0003 (7) |
C7 | 0.0237 (9) | 0.0264 (9) | 0.0185 (8) | 0.0025 (7) | 0.0014 (6) | −0.0047 (7) |
C71 | 0.0222 (9) | 0.0233 (9) | 0.0248 (8) | 0.0016 (7) | 0.0021 (7) | 0.0029 (7) |
C72 | 0.0295 (10) | 0.0293 (10) | 0.0245 (9) | 0.0027 (8) | 0.0008 (7) | −0.0012 (7) |
C73 | 0.0249 (10) | 0.0278 (9) | 0.0310 (9) | 0.0009 (7) | −0.0027 (7) | −0.0002 (7) |
N74 | 0.0253 (8) | 0.0334 (9) | 0.0329 (8) | 0.0006 (6) | 0.0046 (6) | 0.0038 (6) |
C75 | 0.0283 (11) | 0.0378 (10) | 0.0262 (9) | 0.0022 (8) | 0.0062 (7) | 0.0010 (8) |
C76 | 0.0244 (10) | 0.0323 (10) | 0.0232 (8) | 0.0021 (7) | 0.0007 (7) | 0.0003 (7) |
C7A | 0.0229 (9) | 0.0244 (9) | 0.0195 (8) | 0.0000 (7) | 0.0010 (6) | −0.0028 (7) |
C8 | 0.0260 (10) | 0.0271 (9) | 0.0242 (8) | −0.0001 (7) | 0.0010 (7) | −0.0003 (7) |
C81 | 0.0288 (10) | 0.0353 (10) | 0.0336 (10) | −0.0022 (8) | 0.0066 (8) | 0.0045 (8) |
N9 | 0.0271 (8) | 0.0287 (8) | 0.0276 (8) | −0.0024 (6) | 0.0039 (6) | 0.0027 (6) |
N10 | 0.0240 (8) | 0.0247 (8) | 0.0261 (7) | 0.0022 (6) | 0.0024 (6) | 0.0057 (6) |
C101 | 0.0258 (10) | 0.0296 (10) | 0.0194 (8) | 0.0066 (7) | 0.0004 (7) | 0.0005 (7) |
C102 | 0.0373 (11) | 0.0276 (10) | 0.0336 (9) | 0.0040 (8) | −0.0055 (8) | −0.0017 (8) |
C103 | 0.0510 (13) | 0.0313 (11) | 0.0364 (10) | 0.0155 (10) | −0.0048 (9) | −0.0038 (8) |
C104 | 0.0381 (12) | 0.0539 (13) | 0.0263 (9) | 0.0233 (10) | 0.0054 (8) | 0.0063 (9) |
C105 | 0.0280 (11) | 0.0516 (12) | 0.0339 (10) | 0.0083 (9) | 0.0084 (8) | 0.0156 (9) |
C106 | 0.0277 (10) | 0.0315 (10) | 0.0297 (9) | 0.0057 (8) | 0.0031 (7) | 0.0093 (8) |
C10A | 0.0245 (9) | 0.0236 (9) | 0.0181 (8) | 0.0021 (7) | 0.0001 (6) | −0.0019 (7) |
N11 | 0.0237 (8) | 0.0222 (7) | 0.0205 (7) | 0.0021 (6) | 0.0012 (6) | −0.0010 (6) |
C11A | 0.0244 (9) | 0.0209 (8) | 0.0173 (7) | 0.0037 (7) | −0.0004 (6) | −0.0030 (6) |
C11B | 0.0268 (10) | 0.0230 (9) | 0.0170 (7) | 0.0018 (7) | 0.0019 (7) | −0.0046 (7) |
C1—C2 | 1.377 (2) | C75—H75 | 0.95 |
C1—C11B | 1.402 (2) | C76—H76 | 0.95 |
C1—H1 | 0.95 | C7A—C10A | 1.409 (2) |
C2—C3 | 1.394 (2) | C7A—C8 | 1.437 (2) |
C2—H2 | 0.95 | C8—N9 | 1.318 (2) |
C3—C4 | 1.374 (2) | C8—C81 | 1.491 (2) |
C3—H3 | 0.95 | C81—H81A | 0.98 |
C4—C4A | 1.400 (2) | C81—H81B | 0.98 |
C4—H4 | 0.95 | C81—H81C | 0.98 |
C4A—C11B | 1.407 (2) | N9—N10 | 1.3865 (18) |
C4A—C5 | 1.447 (2) | N10—C10A | 1.373 (2) |
C5—C6 | 1.344 (2) | N10—C101 | 1.423 (2) |
C5—H5 | 0.95 | C101—C106 | 1.385 (2) |
C6—C6A | 1.453 (2) | C101—C102 | 1.390 (2) |
C6—H6 | 0.95 | C102—C103 | 1.385 (3) |
C6A—C7 | 1.410 (2) | C102—H102 | 0.95 |
C6A—C11A | 1.430 (2) | C103—C104 | 1.379 (3) |
C7—C7A | 1.396 (2) | C103—H103 | 0.95 |
C7—C71 | 1.490 (2) | C104—C105 | 1.382 (3) |
C71—C76 | 1.389 (2) | C104—H104 | 0.95 |
C71—C72 | 1.393 (2) | C105—C106 | 1.387 (2) |
C72—C73 | 1.376 (2) | C105—H105 | 0.95 |
C72—H72 | 0.95 | C106—H106 | 0.95 |
C73—N74 | 1.339 (2) | C10A—N11 | 1.334 (2) |
C73—H73 | 0.95 | N11—C11A | 1.349 (2) |
N74—C75 | 1.342 (2) | C11A—C11B | 1.461 (2) |
C75—C76 | 1.380 (2) | ||
C2—C1—C11B | 120.88 (15) | C7—C7A—C8 | 137.32 (15) |
C2—C1—H1 | 119.6 | C10A—C7A—C8 | 104.92 (14) |
C11B—C1—H1 | 119.6 | N9—C8—C7A | 110.37 (14) |
C1—C2—C3 | 120.24 (16) | N9—C8—C81 | 119.65 (15) |
C1—C2—H2 | 119.9 | C7A—C8—C81 | 129.97 (15) |
C3—C2—H2 | 119.9 | C8—C81—H81A | 109.5 |
C4—C3—C2 | 119.52 (16) | C8—C81—H81B | 109.5 |
C4—C3—H3 | 120.2 | H81A—C81—H81B | 109.5 |
C2—C3—H3 | 120.2 | C8—C81—H81C | 109.5 |
C3—C4—C4A | 121.42 (16) | H81A—C81—H81C | 109.5 |
C3—C4—H4 | 119.3 | H81B—C81—H81C | 109.5 |
C4A—C4—H4 | 119.3 | C8—N9—N10 | 107.56 (13) |
C4—C4A—C11B | 118.99 (16) | C10A—N10—N9 | 110.11 (13) |
C4—C4A—C5 | 121.70 (16) | C10A—N10—C101 | 129.60 (14) |
C11B—C4A—C5 | 119.31 (15) | N9—N10—C101 | 119.66 (13) |
C6—C5—C4A | 121.68 (16) | C106—C101—C102 | 120.51 (16) |
C6—C5—H5 | 119.2 | C106—C101—N10 | 120.70 (15) |
C4A—C5—H5 | 119.2 | C102—C101—N10 | 118.78 (15) |
C5—C6—C6A | 121.50 (17) | C103—C102—C101 | 119.42 (18) |
C5—C6—H6 | 119.3 | C103—C102—H102 | 120.3 |
C6A—C6—H6 | 119.3 | C101—C102—H102 | 120.3 |
C7—C6A—C11A | 119.65 (14) | C104—C103—C102 | 120.60 (18) |
C7—C6A—C6 | 122.10 (15) | C104—C103—H103 | 119.7 |
C11A—C6A—C6 | 118.23 (15) | C102—C103—H103 | 119.7 |
C7A—C7—C6A | 117.12 (15) | C103—C104—C105 | 119.52 (18) |
C7A—C7—C71 | 121.74 (14) | C103—C104—H104 | 120.2 |
C6A—C7—C71 | 121.11 (14) | C105—C104—H104 | 120.2 |
C76—C71—C72 | 117.17 (15) | C104—C105—C106 | 120.86 (18) |
C76—C71—C7 | 120.90 (14) | C104—C105—H105 | 119.6 |
C72—C71—C7 | 121.91 (14) | C106—C105—H105 | 119.6 |
C73—C72—C71 | 119.29 (15) | C101—C106—C105 | 119.08 (17) |
C73—C72—H72 | 120.4 | C101—C106—H106 | 120.5 |
C71—C72—H72 | 120.4 | C105—C106—H106 | 120.5 |
N74—C73—C72 | 124.28 (15) | N11—C10A—N10 | 125.53 (15) |
N74—C73—H73 | 117.9 | N11—C10A—C7A | 127.43 (14) |
C72—C73—H73 | 117.9 | N10—C10A—C7A | 107.02 (14) |
C73—N74—C75 | 115.91 (14) | C10A—N11—C11A | 114.60 (14) |
N74—C75—C76 | 124.01 (15) | N11—C11A—C6A | 123.51 (14) |
N74—C75—H75 | 118.0 | N11—C11A—C11B | 116.62 (14) |
C76—C75—H75 | 118.0 | C6A—C11A—C11B | 119.81 (14) |
C75—C76—C71 | 119.33 (15) | C1—C11B—C4A | 118.95 (15) |
C75—C76—H76 | 120.3 | C1—C11B—C11A | 121.57 (14) |
C71—C76—H76 | 120.3 | C4A—C11B—C11A | 119.44 (15) |
C7—C7A—C10A | 117.68 (14) | ||
C11B—C1—C2—C3 | 0.2 (2) | C10A—N10—C101—C106 | −38.1 (2) |
C1—C2—C3—C4 | −0.1 (3) | N9—N10—C101—C106 | 151.94 (15) |
C2—C3—C4—C4A | −0.3 (3) | C10A—N10—C101—C102 | 142.43 (17) |
C3—C4—C4A—C11B | 0.6 (3) | N9—N10—C101—C102 | −27.6 (2) |
C3—C4—C4A—C5 | −178.43 (17) | C106—C101—C102—C103 | 0.0 (2) |
C4—C4A—C5—C6 | 176.90 (18) | N10—C101—C102—C103 | 179.54 (15) |
C11B—C4A—C5—C6 | −2.2 (3) | C101—C102—C103—C104 | 0.4 (3) |
C4A—C5—C6—C6A | 1.9 (3) | C102—C103—C104—C105 | −0.2 (3) |
C5—C6—C6A—C7 | −178.16 (18) | C103—C104—C105—C106 | −0.4 (3) |
C5—C6—C6A—C11A | −0.1 (3) | C102—C101—C106—C105 | −0.6 (2) |
C11A—C6A—C7—C7A | 0.9 (2) | N10—C101—C106—C105 | 179.86 (14) |
C6—C6A—C7—C7A | 178.95 (15) | C104—C105—C106—C101 | 0.8 (3) |
C11A—C6A—C7—C71 | −177.14 (13) | N9—N10—C10A—N11 | 177.00 (14) |
C6—C6A—C7—C71 | 0.9 (2) | C101—N10—C10A—N11 | 6.2 (3) |
C7A—C7—C71—C76 | −64.3 (2) | N9—N10—C10A—C7A | −1.51 (17) |
C6A—C7—C71—C76 | 113.68 (17) | C101—N10—C10A—C7A | −172.26 (14) |
C7A—C7—C71—C72 | 117.68 (18) | C7—C7A—C10A—N11 | 0.1 (2) |
C6A—C7—C71—C72 | −64.3 (2) | C8—C7A—C10A—N11 | −177.24 (15) |
C76—C71—C72—C73 | −0.4 (2) | C7—C7A—C10A—N10 | 178.58 (13) |
C7—C71—C72—C73 | 177.73 (15) | C8—C7A—C10A—N10 | 1.23 (16) |
C71—C72—C73—N74 | 0.5 (3) | N10—C10A—N11—C11A | −177.85 (14) |
C72—C73—N74—C75 | 0.0 (2) | C7A—C10A—N11—C11A | 0.3 (2) |
C73—N74—C75—C76 | −0.7 (3) | C10A—N11—C11A—C6A | −0.2 (2) |
N74—C75—C76—C71 | 0.8 (3) | C10A—N11—C11A—C11B | −177.45 (13) |
C72—C71—C76—C75 | −0.3 (2) | C7—C6A—C11A—N11 | −0.5 (2) |
C7—C71—C76—C75 | −178.39 (15) | C6—C6A—C11A—N11 | −178.58 (14) |
C6A—C7—C7A—C10A | −0.8 (2) | C7—C6A—C11A—C11B | 176.72 (14) |
C71—C7—C7A—C10A | 177.31 (13) | C6—C6A—C11A—C11B | −1.4 (2) |
C6A—C7—C7A—C8 | 175.47 (17) | C2—C1—C11B—C4A | 0.1 (2) |
C71—C7—C7A—C8 | −6.5 (3) | C2—C1—C11B—C11A | 178.00 (15) |
C7—C7A—C8—N9 | −177.09 (17) | C4—C4A—C11B—C1 | −0.6 (2) |
C10A—C7A—C8—N9 | −0.55 (17) | C5—C4A—C11B—C1 | 178.54 (15) |
C7—C7A—C8—C81 | 1.6 (3) | C4—C4A—C11B—C11A | −178.46 (15) |
C10A—C7A—C8—C81 | 178.14 (16) | C5—C4A—C11B—C11A | 0.6 (2) |
C7A—C8—N9—N10 | −0.36 (18) | N11—C11A—C11B—C1 | 0.6 (2) |
C81—C8—N9—N10 | −179.20 (13) | C6A—C11A—C11B—C1 | −176.77 (14) |
C8—N9—N10—C10A | 1.17 (17) | N11—C11A—C11B—C4A | 178.49 (14) |
C8—N9—N10—C101 | 172.98 (13) | C6A—C11A—C11B—C4A | 1.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···N11i | 0.95 | 2.56 | 3.404 (2) | 149 |
C75—H75···Cg2ii | 0.95 | 2.60 | 3.463 (2) | 151 |
C4—H4···Cg3iii | 0.95 | 2.84 | 3.771 (2) | 165 |
C4—H4···Cg4iii | 0.95 | 2.92 | 3.700 (2) | 140 |
C103—H103···Cg5iv | 0.95 | 2.87 | 3.749 (2) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, −y−1/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
Experimental details
(IV) | (V) | (VIII) | (IX) | |
Crystal data | ||||
Chemical formula | C27H20ClN3 | C26H20N4 | C28H23N3 | C28H23N3O |
Mr | 421.91 | 388.46 | 401.49 | 417.49 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 120 | 120 | 118 | 120 |
a, b, c (Å) | 12.1072 (4), 14.2672 (5), 12.7635 (4) | 11.2274 (6), 13.7079 (8), 12.6935 (7) | 11.1334 (3), 11.4672 (2), 17.6270 (4) | 18.0854 (3), 21.2296 (5), 23.8007 (5) |
α, β, γ (°) | 90, 109.953 (8), 90 | 90, 95.731 (3), 90 | 97.858 (2), 106.135 (3), 97.496 (2) | 90, 108.258 (1), 90 |
V (Å3) | 2072.37 (16) | 1943.82 (19) | 2107.66 (9) | 8678.1 (3) |
Z | 4 | 4 | 4 | 16 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.21 | 0.08 | 0.08 | 0.08 |
Crystal size (mm) | 0.38 × 0.38 × 0.10 | 0.12 × 0.10 × 0.02 | 0.20 × 0.18 × 0.12 | 0.90 × 0.30 × 0.10 |
Data collection | ||||
Diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.936, 0.980 | 0.987, 0.998 | 0.982, 0.991 | 0.934, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23840, 4752, 3209 | 19684, 4456, 2654 | 40500, 9647, 7878 | 99695, 19715, 8289 |
Rint | 0.052 | 0.085 | 0.048 | 0.166 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.650 | 0.650 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.130, 1.02 | 0.068, 0.137, 1.03 | 0.044, 0.108, 1.03 | 0.096, 0.169, 0.98 |
No. of reflections | 4752 | 4456 | 9647 | 19715 |
No. of parameters | 281 | 272 | 564 | 1161 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.43 | 0.23, −0.21 | 0.27, −0.25 | 0.26, −0.30 |
Absolute structure | ? | ? | ? | ? |
(XIV) | (XV) | |
Crystal data | ||
Chemical formula | C30H27N3O3 | C26H18N4 |
Mr | 477.55 | 386.44 |
Crystal system, space group | Monoclinic, Cc | Monoclinic, P21/c |
Temperature (K) | 120 | 120 |
a, b, c (Å) | 10.4716 (9), 20.0027 (18), 12.1529 (9) | 11.3560 (3), 17.3507 (5), 9.7577 (2) |
α, β, γ (°) | 90, 107.818 (4), 90 | 90, 97.262 (2), 90 |
V (Å3) | 2423.4 (4) | 1907.18 (8) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.08 |
Crystal size (mm) | 0.60 × 0.30 × 0.02 | 0.50 × 0.24 × 0.10 |
Data collection | ||
Diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.963, 0.998 | 0.971, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20344, 2720, 1499 | 26391, 4372, 2818 |
Rint | 0.199 | 0.064 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.152, 1.08 | 0.050, 0.142, 1.01 |
No. of reflections | 2720 | 4372 |
No. of parameters | 329 | 272 |
No. of restraints | 2 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.55 | 0.33, −0.34 |
Absolute structure | Friedel pairs merged | ? |
Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) & COLLECT, DENZO & COLLECT, Sir2004 (Burla et al., 2005), OSCAIL (McArdle, 2003 & SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 & PRPKAPPA (Ferguson, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···Cg1i | 0.95 | 2.88 | 3.823 (2) | 170 |
C75—H75···Cg2ii | 0.95 | 2.94 | 3.860 (2) | 164 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···Cg1i | 0.95 | 2.79 | 3.706 (3) | 163 |
C75—H75···Cg2ii | 0.95 | 2.66 | 3.431 (3) | 139 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···Cg6i | 0.95 | 2.89 | 3.662 (2) | 136 |
C122—H122···Cg7 | 0.95 | 2.75 | 3.412 (2) | 127 |
C125—H125···Cg8ii | 0.95 | 2.87 | 3.772 (2) | 160 |
C222—H222···Cg9 | 0.95 | 2.75 | 3.322 (2) | 119 |
C225—H225···Cg10iii | 0.95 | 2.93 | 3.834 (2) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···N39 | 0.95 | 2.60 | 3.504 (3) | 159 |
C326—H326···N47 | 0.95 | 2.59 | 3.526 (3) | 168 |
C122—H122···Cg11 | 0.95 | 2.77 | 3.542 (3) | 139 |
C222—H222···Cg12i | 0.95 | 2.77 | 3.568 (3) | 142 |
C225—H225···Cg8ii | 0.95 | 2.76 | 3.628 (3) | 152 |
C322—H322···Cg7iii | 0.95 | 2.77 | 3.483 (3) | 132 |
C422—H422···Cg9 | 0.95 | 2.83 | 3.693 (3) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C82—H82···Cg13i | 0.95 | 2.73 | 3.472 (6) | 130 |
Symmetry code: (i) x+1, −y, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C72—H72···N11i | 0.95 | 2.56 | 3.404 (2) | 149 |
C75—H75···Cg2ii | 0.95 | 2.60 | 3.463 (2) | 151 |
C4—H4···Cg3iii | 0.95 | 2.84 | 3.771 (2) | 165 |
C4—H4···Cg4iii | 0.95 | 2.92 | 3.700 (2) | 140 |
C103—H103···Cg5iv | 0.95 | 2.87 | 3.749 (2) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, −y−1/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2. |
In full text version