Molecules of the title compound, C27H23N3O2, contain four rings that are not coplanar and the pyrimidine ring is slightly distorted from planarity. The dihedral angles between pairs of benzene rings are 88.6 (1), 88.6 (1) and 62.9 (1)°. The three benzene rings form dihedral angles of 55.3 (1), 36.2 (1) and 65.5 (1)° with the pyrimidine ring.
Supporting information
CCDC reference: 642924
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.137
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.19 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.11 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 94.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-(4-Methylbenzoyl)-4-(4-methylphenyl)-1-[(1-phenylethylidene)amino]pyrimidin-
2(1
H)-one
top
Crystal data top
C27H23N3O2 | F(000) = 888 |
Mr = 421.48 | Dx = 1.185 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 37167 reflections |
a = 13.6001 (7) Å | θ = 2.0–27.6° |
b = 17.1608 (10) Å | µ = 0.08 mm−1 |
c = 10.8703 (5) Å | T = 296 K |
β = 111.351 (4)° | Plate, colourless |
V = 2362.9 (2) Å3 | 0.65 × 0.45 × 0.21 mm |
Z = 4 | |
Data collection top
Stoe IPDSII diffractometer | 3269 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.049 |
Plane graphite monochromator | θmax = 26.0°, θmin = 2.0° |
Detector resolution: 6.67 pixels mm-1 | h = −16→16 |
ω scans | k = −21→21 |
29539 measured reflections | l = −13→13 |
4639 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0774P)2 + 0.1415P] where P = (Fo2 + 2Fc2)/3 |
4639 reflections | (Δ/σ)max < 0.001 |
292 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Experimental. IR (KBr) ν (cm-1): 3050–3036 (aromatic C—H), 2911 (aliphatic C—H), 1695
(s), 1650 (s, C═O), 1602–1573 (C═C and C═N). 1H
NMR (DMSO): δ 8.25 (s, 1H at C6), 7.97–7.02 (m, 13H, ArH),
2.35, 2.30, 2.26 (s, 9H, 3 × CH3). Analysis calculated for
C27H23N3O2: C 76.93, H 5.49, N 9.96%; found: C 76.87, H 5.71, N 9.81%. |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.73143 (12) | 0.29963 (9) | 0.82542 (13) | 0.0743 (5) | |
O2 | 0.42370 (10) | 0.30815 (9) | 0.25890 (13) | 0.0690 (5) | |
N1 | 0.84218 (11) | 0.32442 (9) | 0.66503 (16) | 0.0588 (5) | |
N2 | 0.72960 (11) | 0.32175 (8) | 0.61895 (13) | 0.0506 (5) | |
N3 | 0.57722 (12) | 0.34296 (9) | 0.66902 (13) | 0.0517 (5) | |
C1 | 1.00573 (15) | 0.26398 (12) | 0.73428 (19) | 0.0634 (7) | |
C2 | 1.05734 (19) | 0.31927 (18) | 0.8242 (3) | 0.0941 (10) | |
C3 | 1.1690 (2) | 0.3225 (2) | 0.8707 (3) | 0.1157 (13) | |
C4 | 1.2233 (2) | 0.2727 (2) | 0.8226 (3) | 0.1038 (13) | |
C5 | 1.1734 (2) | 0.2196 (2) | 0.7335 (4) | 0.1036 (11) | |
C6 | 1.06542 (19) | 0.21367 (17) | 0.6894 (3) | 0.0891 (10) | |
C7 | 0.88885 (14) | 0.25903 (11) | 0.68336 (17) | 0.0541 (6) | |
C8 | 0.83659 (18) | 0.18191 (13) | 0.6575 (3) | 0.0829 (9) | |
C9 | 0.68015 (15) | 0.31939 (10) | 0.71185 (17) | 0.0536 (6) | |
C10 | 0.52343 (13) | 0.35652 (9) | 0.54317 (15) | 0.0448 (5) | |
C11 | 0.56895 (13) | 0.34663 (9) | 0.44446 (15) | 0.0452 (5) | |
C12 | 0.67479 (13) | 0.33297 (10) | 0.49017 (16) | 0.0494 (5) | |
C13 | 0.41487 (13) | 0.38656 (9) | 0.51043 (15) | 0.0451 (5) | |
C14 | 0.35261 (14) | 0.35995 (10) | 0.57832 (17) | 0.0528 (6) | |
C15 | 0.25187 (15) | 0.38820 (12) | 0.54846 (19) | 0.0607 (7) | |
C16 | 0.21038 (15) | 0.44447 (11) | 0.4526 (2) | 0.0609 (7) | |
C17 | 0.27328 (15) | 0.47225 (11) | 0.38684 (18) | 0.0569 (6) | |
C18 | 0.37392 (14) | 0.44354 (10) | 0.41482 (16) | 0.0502 (5) | |
C19 | 0.0994 (2) | 0.47447 (17) | 0.4195 (3) | 0.0979 (10) | |
C20 | 0.50751 (13) | 0.34256 (10) | 0.29991 (16) | 0.0491 (5) | |
C21 | 0.55200 (13) | 0.37950 (10) | 0.20805 (15) | 0.0481 (5) | |
C22 | 0.52194 (14) | 0.35137 (11) | 0.07931 (16) | 0.0534 (5) | |
C23 | 0.56017 (16) | 0.38517 (12) | −0.00857 (16) | 0.0588 (6) | |
C24 | 0.62756 (16) | 0.44856 (11) | 0.02730 (17) | 0.0582 (6) | |
C25 | 0.65497 (16) | 0.47764 (11) | 0.15448 (17) | 0.0588 (6) | |
C26 | 0.61857 (14) | 0.44340 (11) | 0.24421 (16) | 0.0541 (6) | |
C27 | 0.6706 (2) | 0.48465 (14) | −0.0689 (2) | 0.0796 (9) | |
H2 | 1.01970 | 0.35460 | 0.85490 | 0.1130* | |
H3 | 1.20510 | 0.35890 | 0.93440 | 0.1390* | |
H4 | 1.29660 | 0.27580 | 0.85240 | 0.1250* | |
H5 | 1.21170 | 0.18610 | 0.70060 | 0.1240* | |
H6 | 1.03160 | 0.17520 | 0.62840 | 0.1070* | |
H8A | 0.76410 | 0.18760 | 0.64870 | 0.1240* | |
H8B | 0.87190 | 0.14740 | 0.72970 | 0.1240* | |
H8C | 0.83990 | 0.16070 | 0.57740 | 0.1240* | |
H12 | 0.70970 | 0.33140 | 0.43080 | 0.0590* | |
H14 | 0.37910 | 0.32280 | 0.64440 | 0.0630* | |
H15 | 0.21080 | 0.36900 | 0.59380 | 0.0730* | |
H17 | 0.24740 | 0.51080 | 0.32290 | 0.0680* | |
H18 | 0.41480 | 0.46260 | 0.36900 | 0.0600* | |
H19A | 0.05140 | 0.43130 | 0.40230 | 0.1470* | |
H19B | 0.08050 | 0.50710 | 0.34260 | 0.1470* | |
H19C | 0.09560 | 0.50410 | 0.49250 | 0.1470* | |
H22 | 0.47570 | 0.30940 | 0.05280 | 0.0640* | |
H23 | 0.54050 | 0.36520 | −0.09370 | 0.0710* | |
H25 | 0.69870 | 0.52100 | 0.17950 | 0.0710* | |
H26 | 0.63880 | 0.46320 | 0.32950 | 0.0650* | |
H27A | 0.74480 | 0.47380 | −0.04130 | 0.1190* | |
H27B | 0.65990 | 0.54000 | −0.07140 | 0.1190* | |
H27C | 0.63470 | 0.46320 | −0.15520 | 0.1190* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0700 (9) | 0.0952 (11) | 0.0530 (7) | 0.0103 (8) | 0.0169 (6) | 0.0155 (7) |
O2 | 0.0554 (8) | 0.0908 (10) | 0.0647 (8) | −0.0206 (7) | 0.0265 (6) | −0.0277 (7) |
N1 | 0.0434 (8) | 0.0594 (9) | 0.0690 (9) | −0.0035 (7) | 0.0149 (7) | 0.0027 (7) |
N2 | 0.0445 (8) | 0.0525 (8) | 0.0544 (8) | 0.0012 (6) | 0.0177 (6) | 0.0024 (6) |
N3 | 0.0549 (9) | 0.0565 (8) | 0.0467 (7) | 0.0008 (7) | 0.0220 (6) | 0.0017 (6) |
C1 | 0.0479 (10) | 0.0754 (13) | 0.0621 (11) | 0.0009 (9) | 0.0143 (8) | 0.0167 (9) |
C2 | 0.0607 (13) | 0.124 (2) | 0.0895 (16) | −0.0222 (14) | 0.0177 (12) | −0.0187 (15) |
C3 | 0.0757 (19) | 0.161 (3) | 0.0949 (19) | −0.038 (2) | 0.0125 (15) | −0.013 (2) |
C4 | 0.0561 (15) | 0.147 (3) | 0.101 (2) | 0.0081 (18) | 0.0200 (15) | 0.050 (2) |
C5 | 0.0632 (15) | 0.121 (2) | 0.130 (2) | 0.0244 (16) | 0.0393 (16) | 0.037 (2) |
C6 | 0.0619 (14) | 0.0933 (17) | 0.1104 (19) | 0.0163 (12) | 0.0293 (13) | 0.0111 (14) |
C7 | 0.0487 (10) | 0.0588 (11) | 0.0515 (9) | 0.0007 (8) | 0.0143 (7) | 0.0031 (8) |
C8 | 0.0605 (13) | 0.0597 (12) | 0.1163 (19) | −0.0006 (10) | 0.0175 (12) | −0.0056 (12) |
C9 | 0.0569 (10) | 0.0549 (10) | 0.0504 (9) | 0.0010 (8) | 0.0211 (8) | 0.0043 (7) |
C10 | 0.0501 (9) | 0.0406 (8) | 0.0470 (8) | −0.0032 (7) | 0.0217 (7) | −0.0017 (6) |
C11 | 0.0454 (9) | 0.0470 (8) | 0.0467 (8) | −0.0019 (7) | 0.0208 (7) | −0.0033 (7) |
C12 | 0.0519 (10) | 0.0510 (9) | 0.0493 (9) | −0.0026 (8) | 0.0233 (7) | −0.0055 (7) |
C13 | 0.0496 (9) | 0.0439 (8) | 0.0458 (8) | −0.0025 (7) | 0.0221 (7) | −0.0048 (6) |
C14 | 0.0563 (10) | 0.0548 (10) | 0.0550 (9) | 0.0005 (8) | 0.0294 (8) | 0.0019 (8) |
C15 | 0.0610 (11) | 0.0636 (11) | 0.0718 (12) | −0.0033 (9) | 0.0414 (9) | −0.0030 (9) |
C16 | 0.0523 (11) | 0.0578 (11) | 0.0769 (12) | 0.0017 (8) | 0.0287 (9) | −0.0058 (9) |
C17 | 0.0586 (11) | 0.0493 (9) | 0.0630 (10) | 0.0047 (8) | 0.0225 (9) | 0.0024 (8) |
C18 | 0.0543 (10) | 0.0498 (9) | 0.0516 (9) | −0.0012 (8) | 0.0253 (8) | −0.0002 (7) |
C19 | 0.0656 (14) | 0.0984 (18) | 0.138 (2) | 0.0190 (13) | 0.0469 (15) | 0.0116 (17) |
C20 | 0.0447 (9) | 0.0546 (9) | 0.0504 (9) | −0.0006 (8) | 0.0201 (7) | −0.0122 (7) |
C21 | 0.0458 (9) | 0.0556 (9) | 0.0419 (8) | 0.0058 (7) | 0.0148 (7) | −0.0050 (7) |
C22 | 0.0521 (10) | 0.0588 (10) | 0.0451 (8) | 0.0066 (8) | 0.0126 (7) | −0.0060 (7) |
C23 | 0.0687 (12) | 0.0666 (11) | 0.0393 (8) | 0.0149 (9) | 0.0175 (8) | −0.0017 (8) |
C24 | 0.0700 (12) | 0.0595 (11) | 0.0494 (9) | 0.0193 (9) | 0.0268 (8) | 0.0104 (8) |
C25 | 0.0695 (12) | 0.0551 (10) | 0.0549 (10) | −0.0014 (9) | 0.0262 (9) | 0.0001 (8) |
C26 | 0.0622 (11) | 0.0577 (10) | 0.0429 (8) | −0.0012 (8) | 0.0197 (8) | −0.0061 (7) |
C27 | 0.1121 (19) | 0.0744 (14) | 0.0659 (12) | 0.0112 (13) | 0.0488 (12) | 0.0147 (10) |
Geometric parameters (Å, º) top
O1—C9 | 1.224 (2) | C21—C26 | 1.385 (3) |
O2—C20 | 1.215 (2) | C22—C23 | 1.372 (3) |
N1—N2 | 1.428 (2) | C23—C24 | 1.384 (3) |
N1—C7 | 1.269 (2) | C24—C25 | 1.387 (2) |
N2—C9 | 1.403 (2) | C24—C27 | 1.505 (3) |
N2—C12 | 1.339 (2) | C25—C26 | 1.376 (3) |
N3—C9 | 1.366 (3) | C2—H2 | 0.9300 |
N3—C10 | 1.316 (2) | C3—H3 | 0.9300 |
C1—C2 | 1.360 (4) | C4—H4 | 0.9300 |
C1—C6 | 1.390 (4) | C5—H5 | 0.9300 |
C1—C7 | 1.483 (3) | C6—H6 | 0.9300 |
C2—C3 | 1.416 (4) | C8—H8A | 0.9600 |
C3—C4 | 1.353 (4) | C8—H8B | 0.9600 |
C4—C5 | 1.323 (5) | C8—H8C | 0.9600 |
C5—C6 | 1.373 (4) | C12—H12 | 0.9300 |
C7—C8 | 1.480 (3) | C14—H14 | 0.9300 |
C10—C11 | 1.431 (2) | C15—H15 | 0.9300 |
C10—C13 | 1.480 (3) | C17—H17 | 0.9300 |
C11—C12 | 1.361 (3) | C18—H18 | 0.9300 |
C11—C20 | 1.489 (2) | C19—H19A | 0.9600 |
C13—C14 | 1.388 (3) | C19—H19B | 0.9600 |
C13—C18 | 1.387 (2) | C19—H19C | 0.9600 |
C14—C15 | 1.376 (3) | C22—H22 | 0.9300 |
C15—C16 | 1.382 (3) | C23—H23 | 0.9300 |
C16—C17 | 1.384 (3) | C25—H25 | 0.9300 |
C16—C19 | 1.509 (4) | C26—H26 | 0.9300 |
C17—C18 | 1.380 (3) | C27—H27A | 0.9600 |
C20—C21 | 1.485 (2) | C27—H27B | 0.9600 |
C21—C22 | 1.394 (2) | C27—H27C | 0.9600 |
| | | |
O1···N1 | 2.721 (2) | C12···H26 | 2.7700 |
O1···C7 | 3.140 (3) | C15···H26iv | 3.0100 |
O1···C8 | 3.370 (3) | C16···H26iv | 2.9600 |
O1···C8i | 3.379 (3) | C17···H26iv | 3.0800 |
O1···C12i | 3.160 (2) | C20···H18 | 2.6600 |
O2···C18 | 3.093 (2) | C21···H27Bviii | 3.0500 |
O2···C5ii | 3.348 (3) | C21···H12 | 2.7100 |
O2···C13 | 3.089 (2) | C22···H27Bviii | 3.0700 |
O2···C4ii | 3.348 (3) | C23···H8Aiii | 2.9500 |
O1···H12i | 2.5900 | C24···H8Aiii | 2.9800 |
O1···H8A | 2.8600 | C26···H12 | 2.7400 |
O1···H8Ci | 2.6800 | H2···N1 | 2.5900 |
O2···H22 | 2.5800 | H3···H27Bix | 2.5700 |
O2···H4ii | 2.7200 | H4···O2vi | 2.7200 |
O2···H5ii | 2.7200 | H5···O2vi | 2.7200 |
O2···H14iii | 2.5300 | H6···C8 | 2.7900 |
N1···O1 | 2.721 (2) | H6···H8C | 2.4700 |
N1···H2 | 2.5900 | H8A···O1 | 2.8600 |
N2···H8A | 2.3500 | H8A···N2 | 2.3500 |
N2···H17iv | 2.9300 | H8A···C9 | 2.7300 |
N3···H14 | 2.6300 | H8A···C12 | 3.0200 |
N3···H23v | 2.8300 | H8A···C23i | 2.9500 |
N3···H27Cv | 2.7300 | H8A···C24i | 2.9800 |
C4···O2vi | 3.348 (3) | H8B···C6 | 3.0400 |
C4···C14vi | 3.527 (4) | H8C···C6 | 3.0000 |
C5···O2vi | 3.348 (3) | H8C···H6 | 2.4700 |
C7···O1 | 3.140 (3) | H8C···O1iii | 2.6800 |
C8···O1iii | 3.379 (3) | H12···C21 | 2.7100 |
C8···C24i | 3.488 (3) | H12···C26 | 2.7400 |
C8···O1 | 3.370 (3) | H12···H26 | 2.5500 |
C8···C9 | 3.370 (3) | H12···O1iii | 2.5900 |
C8···C12 | 3.458 (3) | H14···N3 | 2.6300 |
C9···C8 | 3.370 (3) | H14···O2i | 2.5300 |
C10···C22i | 3.590 (2) | H15···C4x | 2.9400 |
C12···C17iv | 3.574 (3) | H17···H19B | 2.3600 |
C12···C8 | 3.458 (3) | H17···N2iv | 2.9300 |
C12···C26 | 3.136 (2) | H18···C11 | 2.7900 |
C12···O1iii | 3.160 (2) | H18···C20 | 2.6600 |
C13···O2 | 3.089 (2) | H18···H27Cviii | 2.5200 |
C14···C4ii | 3.527 (4) | H19B···H17 | 2.3600 |
C17···C12iv | 3.574 (3) | H22···O2 | 2.5800 |
C18···O2 | 3.093 (2) | H22···C10iii | 2.9300 |
C18···C20 | 3.085 (3) | H23···N3xi | 2.8300 |
C20···C18 | 3.085 (3) | H23···H27C | 2.3500 |
C22···C10iii | 3.590 (2) | H26···C11 | 2.7100 |
C24···C8iii | 3.488 (3) | H26···C12 | 2.7700 |
C26···C12 | 3.136 (2) | H26···H12 | 2.5500 |
C4···H15vii | 2.9400 | H26···C15iv | 3.0100 |
C6···H8B | 3.0400 | H26···C16iv | 2.9600 |
C6···H8C | 3.0000 | H26···C17iv | 3.0800 |
C8···H6 | 2.7900 | H27B···C21viii | 3.0500 |
C9···H8A | 2.7300 | H27B···C22viii | 3.0700 |
C9···H27Cv | 3.0400 | H27B···H3ix | 2.5700 |
C10···H22i | 2.9300 | H27C···N3xi | 2.7300 |
C11···H26 | 2.7100 | H27C···C9xi | 3.0400 |
C11···H18 | 2.7900 | H27C···H23 | 2.3500 |
C12···H8A | 3.0200 | H27C···H18viii | 2.5200 |
| | | |
N2—N1—C7 | 115.97 (15) | C21—C26—C25 | 120.25 (16) |
N1—N2—C9 | 118.83 (14) | C1—C2—H2 | 120.00 |
N1—N2—C12 | 118.68 (15) | C3—C2—H2 | 120.00 |
C9—N2—C12 | 121.77 (16) | C2—C3—H3 | 120.00 |
C9—N3—C10 | 121.30 (16) | C4—C3—H3 | 120.00 |
C2—C1—C6 | 118.1 (2) | C3—C4—H4 | 120.00 |
C2—C1—C7 | 120.7 (2) | C5—C4—H4 | 120.00 |
C6—C1—C7 | 121.1 (2) | C4—C5—H5 | 120.00 |
C1—C2—C3 | 119.3 (3) | C6—C5—H5 | 120.00 |
C2—C3—C4 | 120.2 (3) | C1—C6—H6 | 119.00 |
C3—C4—C5 | 120.8 (3) | C5—C6—H6 | 119.00 |
C4—C5—C6 | 120.3 (3) | C7—C8—H8A | 109.00 |
C1—C6—C5 | 121.3 (3) | C7—C8—H8B | 109.00 |
N1—C7—C1 | 114.51 (17) | C7—C8—H8C | 109.00 |
N1—C7—C8 | 125.66 (19) | H8A—C8—H8B | 110.00 |
C1—C7—C8 | 119.83 (18) | H8A—C8—H8C | 109.00 |
O1—C9—N2 | 119.18 (19) | H8B—C8—H8C | 109.00 |
O1—C9—N3 | 124.24 (18) | N2—C12—H12 | 119.00 |
N2—C9—N3 | 116.52 (15) | C11—C12—H12 | 119.00 |
N3—C10—C11 | 122.01 (17) | C13—C14—H14 | 120.00 |
N3—C10—C13 | 116.10 (15) | C15—C14—H14 | 120.00 |
C11—C10—C13 | 121.82 (14) | C14—C15—H15 | 119.00 |
C10—C11—C12 | 115.81 (14) | C16—C15—H15 | 119.00 |
C10—C11—C20 | 124.56 (16) | C16—C17—H17 | 120.00 |
C12—C11—C20 | 119.33 (16) | C18—C17—H17 | 120.00 |
N2—C12—C11 | 121.24 (16) | C13—C18—H18 | 120.00 |
C10—C13—C14 | 120.40 (14) | C17—C18—H18 | 120.00 |
C10—C13—C18 | 121.26 (16) | C16—C19—H19A | 109.00 |
C14—C13—C18 | 118.30 (17) | C16—C19—H19B | 110.00 |
C13—C14—C15 | 120.44 (16) | C16—C19—H19C | 110.00 |
C14—C15—C16 | 121.49 (19) | H19A—C19—H19B | 109.00 |
C15—C16—C17 | 118.1 (2) | H19A—C19—H19C | 109.00 |
C15—C16—C19 | 121.1 (2) | H19B—C19—H19C | 109.00 |
C17—C16—C19 | 120.80 (19) | C21—C22—H22 | 120.00 |
C16—C17—C18 | 120.87 (17) | C23—C22—H22 | 120.00 |
C13—C18—C17 | 120.80 (17) | C22—C23—H23 | 120.00 |
O2—C20—C11 | 120.07 (16) | C24—C23—H23 | 119.00 |
O2—C20—C21 | 121.21 (15) | C24—C25—H25 | 119.00 |
C11—C20—C21 | 118.70 (15) | C26—C25—H25 | 119.00 |
C20—C21—C22 | 119.02 (16) | C21—C26—H26 | 120.00 |
C20—C21—C26 | 122.11 (14) | C25—C26—H26 | 120.00 |
C22—C21—C26 | 118.80 (16) | C24—C27—H27A | 109.00 |
C21—C22—C23 | 120.40 (17) | C24—C27—H27B | 109.00 |
C22—C23—C24 | 121.09 (16) | C24—C27—H27C | 109.00 |
C23—C24—C25 | 118.28 (18) | H27A—C27—H27B | 109.00 |
C23—C24—C27 | 120.86 (17) | H27A—C27—H27C | 110.00 |
C25—C24—C27 | 120.87 (18) | H27B—C27—H27C | 110.00 |
C24—C25—C26 | 121.16 (18) | | |
| | | |
C7—N1—N2—C9 | 89.55 (19) | N3—C10—C11—C12 | −8.8 (2) |
C7—N1—N2—C12 | −100.04 (19) | C11—C10—C13—C18 | −36.2 (2) |
N2—N1—C7—C8 | 1.9 (3) | C20—C11—C12—N2 | −167.50 (15) |
N2—N1—C7—C1 | −178.59 (15) | C10—C11—C20—O2 | −38.8 (3) |
N1—N2—C9—N3 | 158.60 (15) | C12—C11—C20—O2 | 134.71 (19) |
C12—N2—C9—O1 | 171.17 (17) | C12—C11—C20—C21 | −43.8 (2) |
N1—N2—C9—O1 | −18.7 (2) | C10—C11—C20—C21 | 142.72 (17) |
C12—N2—C9—N3 | −11.5 (2) | C10—C11—C12—N2 | 6.5 (2) |
N1—N2—C12—C11 | −166.69 (15) | C10—C13—C14—C15 | 179.61 (16) |
C9—N2—C12—C11 | 3.4 (2) | C18—C13—C14—C15 | 1.7 (3) |
C9—N3—C10—C13 | −176.23 (15) | C10—C13—C18—C17 | −178.73 (16) |
C10—N3—C9—O1 | −173.58 (17) | C14—C13—C18—C17 | −0.8 (2) |
C10—N3—C9—N2 | 9.3 (2) | C13—C14—C15—C16 | −1.2 (3) |
C9—N3—C10—C11 | 0.7 (3) | C14—C15—C16—C17 | −0.2 (3) |
C7—C1—C2—C3 | −179.9 (2) | C14—C15—C16—C19 | 179.3 (2) |
C2—C1—C6—C5 | −0.4 (4) | C15—C16—C17—C18 | 1.1 (3) |
C6—C1—C2—C3 | −1.4 (4) | C19—C16—C17—C18 | −178.5 (2) |
C6—C1—C7—N1 | −140.7 (2) | C16—C17—C18—C13 | −0.6 (3) |
C2—C1—C7—N1 | 37.8 (3) | O2—C20—C21—C22 | −24.4 (3) |
C7—C1—C6—C5 | 178.1 (3) | O2—C20—C21—C26 | 152.49 (19) |
C6—C1—C7—C8 | 38.9 (3) | C11—C20—C21—C22 | 154.10 (17) |
C2—C1—C7—C8 | −142.7 (2) | C11—C20—C21—C26 | −29.0 (3) |
C1—C2—C3—C4 | 2.2 (5) | C20—C21—C22—C23 | 178.82 (18) |
C2—C3—C4—C5 | −1.2 (5) | C26—C21—C22—C23 | 1.8 (3) |
C3—C4—C5—C6 | −0.7 (5) | C20—C21—C26—C25 | −177.61 (18) |
C4—C5—C6—C1 | 1.5 (5) | C22—C21—C26—C25 | −0.7 (3) |
C13—C10—C11—C12 | 167.95 (15) | C21—C22—C23—C24 | −1.2 (3) |
C13—C10—C11—C20 | −18.4 (2) | C22—C23—C24—C25 | −0.5 (3) |
N3—C10—C11—C20 | 164.89 (16) | C22—C23—C24—C27 | 179.1 (2) |
N3—C10—C13—C18 | 140.76 (16) | C23—C24—C25—C26 | 1.7 (3) |
C11—C10—C13—C14 | 145.99 (16) | C27—C24—C25—C26 | −177.9 (2) |
N3—C10—C13—C14 | −37.1 (2) | C24—C25—C26—C21 | −1.0 (3) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1; (vi) x+1, −y+1/2, z+1/2; (vii) x+1, y, z; (viii) −x+1, −y+1, −z; (ix) −x+2, −y+1, −z+1; (x) x−1, y, z; (xi) x, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N2 | 0.96 | 2.35 | 2.758 (3) | 105 |
C12—H12···O1iii | 0.93 | 2.59 | 3.160 (2) | 120 |
C14—H14···O2i | 0.93 | 2.53 | 3.425 (2) | 161 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2. |